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			\| ImageFile = D-sorbitol.svg
			\| ImageSize = 220px
			\| ImageFile1 = Sorbitol-3D-balls.png
			\| ImageSize1 = 220px
			\|IUPACName=<small>D</small>-Glucitol<ref>publications.iupac.org/pac/1996/pdf/6810x1919.pdf</ref>
			\| SystematicName = (2''S'',3''R'',4''R'',5''R'')-Hexane-1,2,3,4,5,6-hexol
			\| OtherNames = <small>D</small>-Sorbitol; Sorbogem; Sorbo
			\| Section1 = {{Chembox Identifiers
			\| ChemSpiderID_Ref = {{chemspidercite\|changed\|chemspider}}
			\| ChemSpiderID = 5576
			\| ChEMBL_Ref = {{ebicite\|changed\|EBI}}
			\| ChEMBL = 1682
			\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\| UNII = 506T60A25R
			\| KEGG = C00794
			\| InChI = 1/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1
			\| InChIKey = FBPFZTCFMRRESA-JGWLITMVSA
			\| StdInChI_Ref = {{stdinchicite\|changed\|pubchem}}
			\| StdInChI = 1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1
			\| StdInChIKey_Ref = {{stdinchicite\|changed\|pubchem}}
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			\| CASNo = 50-70-4
			\| CASNo_Ref = {{cascite\|correct\|CAS}}
			\| PubChem = 5780
			\| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
			\| DrugBank = DB01638
			\| ChEBI_Ref = {{ebicite\|changed\|EBI}}
			\| ChEBI = 17924
			\| SMILES = OC((O)(O)(O)CO)CO
			\| MeSHName = Sorbitol
			}}
			\| Section2 = {{Chembox Properties
			\| C=6 \| H=14 \| O=6
			\| MolarMass = 182.17 g/mol
			\| Appearance = White crystalline powder
			\| Density = 1.49 g/cm<sup>3</sup><ref name=GESTIS>{{GESTIS\|ZVG=30670}}</ref>
			\| MeltingPtC = 94–96
			\| MeltingPt_ref = <ref name=GESTIS/>
			\| Solubility = 2350 g/L<ref name=GESTIS/>
			\| BoilingPtC =
			\| MagSus = -107.80·10<sup>−6</sup> cm<sup>3</sup>/mol
			\| LogP =-4.67<ref name="chemsrc">{{cite web\|url=https://www.chemsrc.com/en/cas/50-70-4_904692.html\|title=Sorbitol_msds}}</ref>
			}}
			\| Section3 =
			\| Section4 =
			\| Section5 =
			\| Section6 = {{Chembox Pharmacology
			\| ATCCode_prefix = A06
			\| ATCCode_suffix = AD18
			\| ATC_Supplemental = {{ATC\|A06\|AG07}} {{ATC\|B05\|CX02}} {{ATC\|V04\|CC01}}
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			\| Section7 = {{Chembox Hazards
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			\| NFPA-F = 1
			\| NFPA-R = 0
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			\| FlashPt = >
			\| FlashPtC= 100
			\| FlashPt_ref = <ref name=GESTIS/>
			\| AutoignitionPtC = 420
			\| AutoignitionPt_ref = <ref name=GESTIS/>
			}}
			}}

			'''Sorbitol''' ({{IPAc-en\|ˈ\|s\|ɔː\|(\|r\|)\|b\|ᵻ\|t\|ɒ\|l}}), less commonly known as '''glucitol''' ({{IPAc-en\|ˈ\|g\|l\|uː\|s\|ᵻ\|t\|ɒ\|l}}), is a ] with a ] ] which the human body metabolizes slowly. It can be obtained by ] of ], which changes the converted ] group (−CHO) to a primary alcohol group (−CH<sub>2</sub>OH). Most sorbitol is made from ], but it is also found in nature, for example in apples, pears, peaches, and prunes.<ref name=Teo>{{cite journal \| pmid = 17132742 \| year = 2006 \| last1 = Teo \| first1 = G \| last2 = Suzuki \| first2 = Y \| last3 = Uratsu \| first3 = SL \| last4 = Lampinen \| first4 = B \| last5 = Ormonde \| first5 = N \| last6 = Hu \| first6 = WK \| last7 = Dejong \| first7 = TM \| last8 = Dandekar \| first8 = AM \| title = Silencing leaf sorbitol synthesis alters long-distance partitioning and apple fruit quality \| volume = 103 \| issue = 49 \| pages = 18842–7 \| doi = 10.1073/pnas.0605873103 \| pmc = 1693749 \| journal = Proceedings of the National Academy of Sciences of the United States of America\| bibcode = 2006PNAS..10318842T \| doi-access = free }}</ref> It is converted to ] by ]. Sorbitol is an ] of ], another sugar alcohol; the two differ only in the orientation of the ] group on carbon{{nbs}}2.<ref name="Kearsley, M. W. pp 249-249">Kearsley, M. W.; Deis, R. C. Sorbitol and Mannitol. In Sweeteners and Sugar Alternatives in Food Technology; Ames: Oxford, 2006; pp 249-249-261.</ref> While similar, the two sugar alcohols have very different sources in nature, ]s, and uses.
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			As an ], sorbitol is used as a ] to treat ].<ref name="drugs">{{cite web \|title=Sorbitol \|url=https://www.drugs.com/mtm/sorbitol.html \|publisher=Drugs.com \|access-date=8 July 2022 \|date=23 November 2021}}</ref>
	! {{chembox header}}\| '''{{PAGENAME}}''' <!-- replace if not identical with the article name -->
	\|-
	\| ]
	\| {{PAGENAME}} <!-- replace if not identical with the article name -->
	\|-
	\| ]
	\| {{carbon}}<sub>6</sub>{{hydrogen}}<sub>14</sub>{{oxygen}}<sub>6</sub>
	\|-
	\| ]
	\| 182.17 g/mol
	\|-
	\| ]
	\| 95°C
	\|-
	\| ]
	\| 295°C
	\|-
	\| ]
	\| x.xxx g/cm<sup>3</sup>
	\|-
	\| ]
	\| 50-70-4
	\|-
	\| ]
	\| OCC(O)C(O)C(O)C(O)CO
	\|-
	\| align="center" colspan="2" \| ]
	\|-
	\| {{chembox header}} \| <small>]</small>
	\|-
	\|}
	</div>
	'''Sorbitol''', also known as '''glucitol''', is a ] the body metabolises slowly. It is obtained by ] of ] taking the ] group to an additional ] group hence the name ''sugar alcohol''.

			==Synthesis==
	Sorbitol is an ] often used in diet ]s (including diet drinks). It is called a nutritive sweetener because it provides 2.6 ]s (11 ]s) per ] versus the 4 calories (17 kJ) of ] and ]. Sorbitol also occurs naturally in many ]s.
			<!-- linked from redirect ] -->
			Sorbitol may be synthesised via a glucose reduction reaction<ref>{{cite web\|title=Reduction of Glucose\|url=http://butane.chem.uiuc.edu/pshapley/GenChem2/B8/1.html\|website=butane.chem.uiuc.edu\|access-date=2017-10-03\|archive-date=2017-09-25\|archive-url=https://web.archive.org/web/20170925133922/http://butane.chem.uiuc.edu/pshapley/GenChem2/B8/1.html\|url-status=dead}}</ref> in which the converted ] group is converted into a ] group. The reaction requires ] and is catalyzed by ]. Glucose reduction is the first step of the ] of ], and is implicated in multiple diabetic complications.

			<chem display="block">C6H12O6 + NADH + H+ -> C6H14O6 + NAD+</chem>The mechanism involves a ] residue in the active site of aldehyde reductase. The hydrogen atom on NADH is transferred to the electrophilic aldehyde carbon atom; electrons on the aldehyde carbon-oxygen double bond are transferred to the oxygen that abstracts the proton on tyrosine side chain to form the hydroxyl group. The role of aldehyde reductase tyrosine phenol group is to serve as a general acid to provide proton to the reduced aldehyde oxygen on glucose.
	Sorbitol is produced naturally by the body, yet sorbitol is poorly ] by the body. Too much sorbitol in ]s can cause damage.

			]
	] ] and ] may be related to excess sorbitol in the cells of the ]s and ]s. The source of this sorbitol in diabetics is excess ], which goes through the ]. Ingesting large amounts of sorbitol can lead to some abdominal pain, gas, and mild to severe ]. Sorbitol can also aggravate ] and ].

			Glucose reduction is not the major ] pathway in a normal human body, where the ] is in the normal range. However, in diabetic patients whose blood glucose level is high, up to 1/3 of their glucose could go through the glucose reduction pathway. This will consume NADH and eventually leads to cell damage.
	Sorbitol is often used in modern ] as a ] and ]. Some transparent ]s can only be made with sorbitol as it has a ] sufficiently high for transparent formulations. It is also used as a ] in some ]s.

			==Uses==
	Sorbitol is used as a ] additive (mixed with ] and sodium poly]s) in the manufacture of ], a highly ], uncooked ] paste most commonly produced from ] (or walleye) ] (Theragra chalcogramma).

			===Sweetener===
	Sorbitol is identified as a potential key chemical intermediate <ref>''Production of Liquid Hydrocarbons from Biomass '' Jürgen O. Metzger ] Volume 45, Issue 5 , Pages 696 - 698 '''2005''' </ref> from ] resources. Complete reduction of sorbitol opens the way to ]s such as ] which can be used as a ]. Sorbitol itself provides much of the hydrogen required for the transformation.
			Sorbitol is a ], and when used in food it has the ] and ] 420. Sorbitol is about 60% as sweet as sucrose (table sugar).<ref>]</ref>

			Sorbitol is referred to as a nutritive sweetener because it provides some dietary energy. It is partly absorbed from the small intestine and metabolized in the body, and partly fermented in the large intestine. The fermentation produces ]s, ], ], and ], which are mostly absorbed and provide energy, but also ], ], and ] which do not provide energy. Even though the ] of sorbitol is higher than that of glucose (having two extra hydrogen atoms), the net energy contribution is between 2.5 and 3.4 ]s per ], versus the approximately 4 kilocalories (17 kilojoules) for carbohydrates.<ref>{{cite journal \|last1=Tsuneyuki Oku and Sadako Nakamura \|title=Digestion, absorption, fermentation, and metabolism of functional sugar substitutes and their available energy \|journal=Pure Appl. Chem. \|date=2002 \|volume=74 \|issue=7 \|pages=1253–1261 \|doi=10.1351/pac200274071253 \|url=http://media.iupac.org/publications/pac/2002/pdf/7407x1253.pdf}}</ref> It is often used in ]s (including diet drinks and ice cream), mints, ]s, and sugar-free ].<ref>{{cite book \|last1=Campbell \|last2=Farrell \|title=Biochemistry \|publisher=Brooks/Cole \|edition=Seventh \|year=2011 \|isbn=978-1-111-42564-7 }}</ref> Most bacteria cannot use sorbitol for energy, but it can be slowly fermented in the mouth by '']'', a bacterium that causes ]. In contrast, many other sugar alcohols such as ] and ] are considered non-acidogenic.<ref>{{cite journal\|last=Hayes\|first=C.\|date=October 2001\|title=The effect of non-cariogenic sweeteners on the prevention of dental caries: a review of the evidence\|journal=Journal of Dental Education\|volume=65\|issue=10\|pages=1106–1109\|doi=10.1002/j.0022-0337.2001.65.10.tb03457.x\|issn=0022-0337\|pmid=11699985}}</ref><ref>{{cite journal\|last1=Nicolas\|first1=Guillaume G.\|last2=Lavoie\|first2=Marc C.\|date=January 2011\|title=\|journal=Canadian Journal of Microbiology\|volume=57\|issue=1\|pages=1–20\|doi=10.1139/w10-095\|issn=1480-3275\|pmid=21217792}}</ref>
	:<math>19 C_6 O_6 H_{14} \to 13 C_6 H_{14} + 36 C O_2 + 42 H_2 O</math>

			It also occurs naturally in many ]s and berries from trees of the genus '']''.<ref name=Teo/><ref>{{cite book \|last1=Nelson \|last2=Cox \|title=Lehninger Principles of Biochemistry \|location=New York \|publisher=W. H. Freeman \|edition=Fourth \|year=2005 \|isbn=0-7167-4339-6 \|url-access=registration \|url=https://archive.org/details/lehningerprincip00lehn_0 }}</ref>
	The above ] is ] and 1.5 ] of sorbitol generates 1 mole of hexane. When hydrogen is co-fed no ] production takes place. The advantage of hexane as a biofuel over well established other biofuels such as ] is that hexane easily separates from water. In fact, the energy required to distill ethanol from water in the bio-ethanol production process eliminates much of the energy advantages.

			===Medical applications===
	== See also ==
	* ]
	* ]

			====Laxative====
	For Immediate Release: September 27, 1999 Consumer Group Petitions FDA to Require "Diarrhea" Notice on Foods that Contain Sorbitol at by
			As is the case with other ]s, foods containing sorbitol can cause ]. Sorbitol can be used as a ] when taken orally or as an ].<ref name=drugs/> Sorbitol works as a laxative by drawing water into the ], stimulating ].<ref name=drugs/><ref>{{cite web\|url=http://www.cancer.org/docroot/CDG/content/CDG_sorbitol.asp \|publisher=American Cancer Society \|work= Cancer Drug Guide\|title=sorbitol\|archive-url=https://web.archive.org/web/20070630001051/http://www.cancer.org/docroot/CDG/content/CDG_sorbitol.asp \|archive-date=2007-06-30 }}</ref> Sorbitol has been determined safe for use by the elderly, although it is not recommended without the advice of a physician.<ref name=drugs/><ref>{{cite journal \| pmid= 7663066 \| year= 1995 \| last1= Lederle \| first1= FA \| title= Epidemiology of constipation in elderly patients. Drug utilisation and cost-containment strategies \| volume= 6 \| issue= 6 \| pages= 465–9 \| journal= Drugs & Aging \| doi=10.2165/00002512-199506060-00006\| s2cid= 43386314 }}</ref>

	== '''The Center for Science for Public Interest''' ==

			Sorbitol is commonly used orally as a one-time dose of {{convert\|30\|-\|150\|ml}} 70% solution.<ref name=drugs/> It may also be used as a one-time ] enema.<ref name=drugs/>

			====Other medical applications====
	"WASHINGTON - The Center for Science in the Public Interest today petitioned the Food and Drug Administration (FDA) to improve the existing warning label on processed foods that contain the sugar substitute sorbitol. Sorbitol is a sweet-tasting sugar alcohol used in many sugar-free or “dietetic” candies, cake mixes, syrups, and other foods, as well as in some medicines. It provides fewer calories than regular sugars, because it is poorly absorbed by the body.
			Sorbitol is used in bacterial culture media to distinguish the pathogenic ] from most other strains of '']'', because it is usually unable to ferment sorbitol, unlike 93% of known ''E. coli'' strains.<ref name=wells_1983_101>{{cite journal \|vauthors=Wells JG, Davis BR, Wachsmuth IK, etal \|title=Laboratory investigation of hemorrhagic colitis outbreaks associated with a rare Escherichia coli serotype\|journal=Journal of Clinical Microbiology\|volume=18\|issue=3\|pages=512–20\| date=September 1983 \|pmid=6355145\|pmc=270845\|doi=10.1128/JCM.18.3.512-520.1983\|quote=The organism does not ferment sorbitol; whereas 93% of E. coli of human origin are sorbitol positive}}</ref>

			A treatment for ] (elevated blood ]) uses sorbitol and the ] resin ] (tradename Kayexalate).<ref>{{cite journal \|vauthors=Rugolotto S, Gruber M, Solano PD, Chini L, Gobbo S, Pecori S \|title=Necrotizing enterocolitis in a 850 gram infant receiving sorbitol-free sodium polystyrene sulfonate (Kayexalate): clinical and histopathologic findings \|journal=J Perinatol \|volume=27 \|issue=4 \|pages=247–9 \| date=April 2007 \|pmid=17377608 \|doi=10.1038/sj.jp.7211677 \|doi-access=free }}</ref> The resin exchanges sodium ions for potassium ions in the bowel, while sorbitol helps to eliminate it. In 2010, the U.S. ] issued a warning of increased risk for gastrointestinal necrosis with this combination.<ref>{{cite web\|url=https://www.fda.gov/Safety/MedWatch/SafetyInformation/ucm186845.htm\|title=Kayexalate (sodium polystyrene sulfonate) powder\|work=fda.gov\|access-date=12 July 2015}}</ref>
	Studies over the past fifteen years have proven that sorbitol can cause gastrointestinal symptoms, ranging from mild discomfort to severe diarrhea, when adults consume between 10 and 50 grams of the additive. Children, because of their small size, may be affected by even smaller amounts. Currently, the FDA requires a laxative notice only on the few products that may lead to the consumption of 50 grams or more of sorbitol daily, though some companies voluntarily label additional products.

			Sorbitol is also used in the manufacture of ]s to store single doses of liquid medicines.<ref name="Catalent Softgel website">{{cite web\|url=http://www.catalent.com/offerings/drug-delivery/drug-delivery-oral/softgel-technology\|title=Home – Catalent\|work=catalent.com\|access-date=12 July 2015}}</ref>
	“The FDA should require a better label notice on sorbitol-containing products,” said Michael F. Jacobson, Ph.D., executive director of CSPI. “The FDA has known for years that sorbitol can cause severe diarrhea. It’s high time that the Agency required a strong label notice on all products that might cause problems.”

			===Health care, food, and cosmetic uses===
	“Since even small amounts of sorbitol can cause gastrointestinal symptoms it is important for the FDA to inform the public of this potential problem,” said Dr. Jeffrey S. Hyams, Head, Department of Digestive Diseases and Nutrition, Connecticut Children’s Medical Center, and Professor of Pediatrics, Connecticut University School of Medicine. “I know of people who have undergone extensive medical testing for abdominal pain and diarrhea when the problem was simply that they were ingesting excessive amounts of sorbitol.” Dr. Hyams conducted a clinical study in which five of seven adults experienced gastrointestinal symptoms after ingesting 10 grams of sorbitol.
			Sorbitol often is used in modern ] as a ] and ].<ref>{{cite web\|url=http://www.bttcogroup.in/sorbitol-70.html\|title=Sorbitol 70%\|work=bttcogroup.in\|access-date=12 July 2015\|archive-date=10 July 2020\|archive-url=https://web.archive.org/web/20200710015140/http://www.bttcogroup.in/sorbitol-70.html\|url-status=dead}}</ref> It is also used in ] and ]. Some transparent ]s can be made only with sorbitol, because of its high ].

			Sorbitol is used as a ] additive (mixed with ] and sodium poly]s) in the manufacture of ], a processed fish paste.<ref name="MedinaGarrote2002">{{cite journal\|last1=Medina\|first1=J.R.\|last2=Garrote\|first2=R.L.\|title=The effect of two cryoprotectant mixtures on frozen surubí surimi\|journal=Brazilian Journal of Chemical Engineering\|volume=19\|issue=4\|year=2002\|pages=419–424\|issn=0104-6632\|doi=10.1590/S0104-66322002000400010\|doi-access=free}}</ref> It is also used as a humectant in some ]s.<ref>{{cite web\|url=http://www.gallaher-group.com/products/table3_display.asp?brand_name=Benson+%26+Hedges+Gold&brand_family=Benson+%26+Hedges&product_type=CIGARETTE&country=UNITED+KINGDOM\|title=Gallaher Group\|work=gallaher-group.com\|access-date=12 July 2015\|archive-date=27 December 2008\|archive-url=https://web.archive.org/web/20081227113352/http://www.gallaher-group.com/products/table3_display.asp?brand_name=Benson+%26+Hedges+Gold&brand_family=Benson+%26+Hedges&product_type=CIGARETTE&country=UNITED+KINGDOM\|url-status=dead}}</ref>
	Some products that contain more than 10 grams of sorbitol or similar sugar substitute per serving include: Brach’s Star Brites Fruity Candies, Life Savers Delites Hard Candy; Cumberland Packing Corp.’s Sweet ‘N Low Sugar Free, Low Fat Cake Mixes; Frutay Peppermint Drops; Cary’s Maple Syrup; Allen Wertz Simply Sugar Free Chocolate & Vanilla Caramels, Fruit Taffy Whips, and Coffee Toffee.

			Beyond its use as a sugar substitute in reduced-sugar foods, sorbitol is also used as a humectant in cookies and low-moisture foods like peanut butter and fruit preserves.<ref name=":0">{{cite book\|title=Chemical and functional properties of food saccharides\|date=2004\|publisher=CRC Press\|others=Tomasik, Piotr\|isbn=9780203495728\|location=Boca Raton\|oclc=317752036}}</ref> In baking, it is also valuable because it acts as a ], and slows down the ] process.<ref name=":0" />
	“With Halloween coming up, people should be concerned about well-meaning families giving candy to children that could end up giving them severe diarrhea,” said Dr. Ray Breitenbach. Dr. Breitenbach is a practicing family physician and retired United States Air Force Lt. Colonel Flight Surgeon who has written about the risks of eating sorbitol-containing candy.

			===Miscellaneous uses===
	CSPI has petitioned the FDA to require foods containing one or more grams per serving of sorbitol or other sugar alcohol, such as mannitol, to carry a more informative notice. CSPI’s petition recommends that labels state: “NOTICE: This product contains sorbitol, which may cause diarrhea, bloating, and abdominal pain. Not suitable for consumption by children. To protect yourself, start by eating no more than one serving at a time.”
			A mixture of sorbitol and ] has found some success as an ] solid ]. It has similar performance to sucrose-based ], but is easier to cast, less hygroscopic and does not ].<ref>{{Cite web \|last=Nakka \|first=Richard \|title=KNSB Propellant \|url=http://www.nakka-rocketry.net/sorb.html \|access-date=12 July 2015 \|website=nakka-rocketry.net}}</ref>

			Sorbitol is identified as a potential key chemical intermediate<ref>{{cite journal
	== External links ==
			\| last1 = Metzger \| first1 = Jürgen O.
	* — see entry on sorbitol
			\| title = Production of Liquid Hydrocarbons from Biomass
			\| doi = 10.1002/anie.200502895
			\| pmid = 16374789
			\| journal = Angewandte Chemie International Edition
			\| volume = 45
			\| issue = 5
			\| pages = 696–698
			\| year = 2006
			}}</ref> for production of fuels from ] resources. ] fractions in biomass such as ] undergo sequential ] and ] in the presence of metal catalysts to produce sorbitol.<ref>{{cite journal\|last=Shrotri\|first=Abhijit\|author2=Tanksale, Akshat \|author3=Beltramini, Jorge Norberto \|author4=Gurav, Hanmant \|author5= Chilukuri, Satyanarayana V. \|title=Conversion of cellulose to polyols over promoted nickel catalysts\|journal=Catalysis Science & Technology\|year=2012\|volume=2\|issue=9\|pages=1852–1858\|doi=10.1039/C2CY20119D}}</ref> Complete reduction of sorbitol opens the way to ]s, such as ], which can be used as a ]. Hydrogen required for this reaction can be produced by aqueous phase ] of sorbitol.<ref>{{cite journal\|last=Tanksale\|first=Akshat\|author2=Beltramini, Jorge Norberto \|author3=Lu, GaoQing Max \|title=A review of catalytic hydrogen production processes from biomass\|journal=Renewable and Sustainable Energy Reviews\|year=2010\|volume=14\|issue=1\|pages=166–182\|doi=10.1016/j.rser.2009.08.010\|bibcode=2010RSERv..14..166T }}</ref>

			:19 C<sub>6</sub>H<sub>14</sub>O<sub>6</sub> → 13 C<sub>6</sub>H<sub>14</sub> + 36 CO<sub>2</sub> + 42 H<sub>2</sub>O
	== References ==
	<references />

			The above ] is ], and 1.5 ]s of sorbitol generate approximately 1 mole of ]. When hydrogen is co-fed, no ] is produced.
	]
	]
	]

			Sorbitol based polyols are used in the production of ] foam for the construction industry.
	Used in Eclipse Gum, Orbit
	ë

			It is also added after ] of yeasts in transformation protocols, allowing the cells to recover by raising the ] of the medium.
	]

	]
			==Medical importance==
	]
			] is the first enzyme in the ]<ref>{{cite journal \| pmid = 10783895 \| year = 2000 \| last1 = Nishikawa \| first1 = T \| last2 = Edelstein \| first2 = D \| last3 = Du \| first3 = XL \| last4 = Yamagishi \| first4 = S \| last5 = Matsumura \| first5 = T \| last6 = Kaneda \| first6 = Y \| last7 = Yorek \| first7 = MA \| last8 = Beebe \| first8 = D \| last9 = Oates \| first9 = PJ \| last10 = Oates \| first10 = Peter J. \| last11 = Hammes \| first11 = Hans-Peter \| last12 = Giardino \| first12 = Ida \| title = Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage \| volume = 404 \| issue = 6779 \| pages = 787–90 \| doi = 10.1038/35008121 \| journal = Nature \| bibcode = 2000Natur.404..787N \| s2cid = 4426750 \| display-authors = 8 }}</ref> responsible for the reduction of glucose to sorbitol, as well as the reduction of ] to ]. Too much sorbitol trapped in retinal cells, the cells of the lens, and the ] that ]ate peripheral nerves, is a frequent result of long-term hyperglycemia that accompanies poorly controlled ]. This can damage these cells, leading to ], ]s and peripheral ], respectively.
	]

	]
			Sorbitol is fermented in the colon and produces short-chain fatty acids, which are beneficial to overall colon health.<ref name=":2">{{cite journal \| last1 = Islam \| first1 = M. S. \| last2 = Sakaguchi \| first2 = E \| year = 2006 \| title = Sorbitol-based osmotic diarrhea: Possible causes and mechanism of prevention investigated in rats \| journal = World Journal of Gastroenterology \| volume = 12 \| issue = 47\| pages = 7635–7641 \| doi=10.3748/wjg.v12.i47.7635\| pmid = 17171792 \| pmc = 4088045 \| doi-access = free }}</ref>
	]

	]
			==Potential adverse effects==
	]
			Sorbitol may cause ]s in some people.<ref name=drugs/> Common side effects from use as a laxative are ]s, vomiting, ] or rectal bleeding.<ref name=drugs/>
	]

			==Compendial status==
			* ]<ref name=rffs>{{cite web
			\|last = The United States Pharmacopeial Convention
			\|title = Revisions to FCC, First Supplement
			\|url = http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport04.html
			\|access-date = 6 July 2009
			\|url-status = dead
			\|archive-url = https://archive.today/20100705223317/http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport04.html
			\|archive-date = 5 July 2010
			}}</ref>
			* ]<ref name=dsbtl>{{cite web
			\| last = Sigma Aldrich
			\| author-link = Sigma Aldrich
			\| title = D-Sorbitol
			\| url = http://www.sigmaaldrich.com/US/en/product/sial/97336
			\| access-date = 15 February 2022
			}}</ref> 6.1<ref name=ipe>{{cite web\| last =European Pharmacopoeia\| author-link =European Pharmacopoeia\| title =Index, Ph Eur\| url =https://www.edqm.eu/store/images/majbdd/200709201618250.6_1%20IndexE.pdf\| access-date =6 July 2009\| url-status =dead\| archive-url =https://web.archive.org/web/20110720160054/https://www.edqm.eu/store/images/majbdd/200709201618250.6_1%20IndexE.pdf\| archive-date =20 July 2011}}</ref>
			* ] 2009<ref name=ib29>{{cite web
			\|last=British Pharmacopoeia
			\|title=Index, BP 2009
			\|year=2009
			\|url=http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf
			\|access-date=6 July 2009
			\|url-status=dead
			\|archive-url=https://web.archive.org/web/20090411071437/http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf
			\|archive-date=11 April 2009
			}}</ref>
			* ] 17 <ref name=nihs>{{cite web
			\|last=National Institute of Health Sciences
			\|title=The Japanese Pharmacopoeia, Seventeenth Edition
			\|year=2016
			\|url=http://jpdb.nihs.go.jp/jp17e/000217655.pdf
			\|access-date=17 August 2018
			\|archive-date=4 March 2018
			\|archive-url=https://web.archive.org/web/20180304194003/http://jpdb.nihs.go.jp/jp17e/000217655.pdf
			\|url-status=dead
			}}</ref>

			==See also==
			*]
			*]

			==References==
			{{Reflist\|30em}}

			==External links==
			*{{Commons category-inline}}

			{{Alcohols}}
			{{Blood substitutes and perfusion solutions}}
			{{Consumer Food Safety}}
			{{Diagnostic agents}}
			{{Fructose and galactose metabolism enzymes}}
			{{Laxatives}}

			]
			]
			]
			]
			]
			]
			]

Latest revision as of 21:14, 31 December 2024

Sorbitol
Names


IUPAC name D-Glucitol
Systematic IUPAC name (2S,3R,4R,5R)-Hexane-1,2,3,4,5,6-hexol
Other names D-Sorbitol; Sorbogem; Sorbo
Identifiers
CAS Number	50-70-4
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17924
ChEMBL	ChEMBL1682
ChemSpider	5576
DrugBank	DB01638
ECHA InfoCard	100.000.056
E number	E420 (thickeners, ...)
KEGG	C00794
MeSH	Sorbitol
PubChem CID	5780
UNII	506T60A25R
CompTox Dashboard (EPA)	DTXSID5023588
InChI InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1Key: FBPFZTCFMRRESA-JGWLITMVSA-N InChI=1/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5-,6-/m1/s1Key: FBPFZTCFMRRESA-JGWLITMVSA
SMILES OC((O)(O)(O)CO)CO
Properties
Chemical formula	C₆H₁₄O₆
Molar mass	182.17 g/mol
Appearance	White crystalline powder
Density	1.49 g/cm
Melting point	94–96 °C (201–205 °F; 367–369 K)
Solubility in water	2350 g/L
log P	-4.67
Magnetic susceptibility (χ)	-107.80·10 cm/mol
Pharmacology
ATC code	A06AD18 (WHO) A06AG07 (WHO) B05CX02 (WHO) V04CC01 (WHO)
Hazards
NFPA 704 (fire diamond)	1 1 0
Flash point	> 100 °C (212 °F; 373 K)
Autoignition temperature	420 °C (788 °F; 693 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Sorbitol (/ˈsɔː(r)bɪtɒl/), less commonly known as glucitol (/ˈɡluːsɪtɒl/), is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alcohol group (−CH₂OH). Most sorbitol is made from potato starch, but it is also found in nature, for example in apples, pears, peaches, and prunes. It is converted to fructose by sorbitol-6-phosphate 2-dehydrogenase. Sorbitol is an isomer of mannitol, another sugar alcohol; the two differ only in the orientation of the hydroxyl group on carbon 2. While similar, the two sugar alcohols have very different sources in nature, melting points, and uses.

As an over-the-counter drug, sorbitol is used as a laxative to treat constipation.

Synthesis

Sorbitol may be synthesised via a glucose reduction reaction in which the converted aldehyde group is converted into a hydroxyl group. The reaction requires NADH and is catalyzed by aldose reductase. Glucose reduction is the first step of the polyol pathway of glucose metabolism, and is implicated in multiple diabetic complications.

${\ce {C6H12O6 + NADH + H+ -> C6H14O6 + NAD+}}$ The mechanism involves a tyrosine residue in the active site of aldehyde reductase. The hydrogen atom on NADH is transferred to the electrophilic aldehyde carbon atom; electrons on the aldehyde carbon-oxygen double bond are transferred to the oxygen that abstracts the proton on tyrosine side chain to form the hydroxyl group. The role of aldehyde reductase tyrosine phenol group is to serve as a general acid to provide proton to the reduced aldehyde oxygen on glucose.

Glucose reduction is not the major glucose metabolism pathway in a normal human body, where the glucose level is in the normal range. However, in diabetic patients whose blood glucose level is high, up to 1/3 of their glucose could go through the glucose reduction pathway. This will consume NADH and eventually leads to cell damage.

Uses

Sweetener

Sorbitol is a sugar substitute, and when used in food it has the INS number and E number 420. Sorbitol is about 60% as sweet as sucrose (table sugar).

Sorbitol is referred to as a nutritive sweetener because it provides some dietary energy. It is partly absorbed from the small intestine and metabolized in the body, and partly fermented in the large intestine. The fermentation produces short-chain fatty acids, acetic acid, propionic acid, and butyric acid, which are mostly absorbed and provide energy, but also carbon dioxide, methane, and hydrogen which do not provide energy. Even though the heat of combustion of sorbitol is higher than that of glucose (having two extra hydrogen atoms), the net energy contribution is between 2.5 and 3.4 kilocalories per gram, versus the approximately 4 kilocalories (17 kilojoules) for carbohydrates. It is often used in diet foods (including diet drinks and ice cream), mints, cough syrups, and sugar-free chewing gum. Most bacteria cannot use sorbitol for energy, but it can be slowly fermented in the mouth by Streptococcus mutans, a bacterium that causes tooth decay. In contrast, many other sugar alcohols such as isomalt and xylitol are considered non-acidogenic.

It also occurs naturally in many stone fruits and berries from trees of the genus Sorbus.

Medical applications

Laxative

As is the case with other sugar alcohols, foods containing sorbitol can cause gastrointestinal distress. Sorbitol can be used as a laxative when taken orally or as an enema. Sorbitol works as a laxative by drawing water into the large intestine, stimulating bowel movements. Sorbitol has been determined safe for use by the elderly, although it is not recommended without the advice of a physician.

Sorbitol is commonly used orally as a one-time dose of 30–150 millilitres (1.1–5.3 imp fl oz; 1.0–5.1 US fl oz) 70% solution. It may also be used as a one-time rectal enema.

Other medical applications

Sorbitol is used in bacterial culture media to distinguish the pathogenic Escherichia coli O157:H7 from most other strains of E. coli, because it is usually unable to ferment sorbitol, unlike 93% of known E. coli strains.

A treatment for hyperkalaemia (elevated blood potassium) uses sorbitol and the ion-exchange resin sodium polystyrene sulfonate (tradename Kayexalate). The resin exchanges sodium ions for potassium ions in the bowel, while sorbitol helps to eliminate it. In 2010, the U.S. FDA issued a warning of increased risk for gastrointestinal necrosis with this combination.

Sorbitol is also used in the manufacture of softgel capsules to store single doses of liquid medicines.

Health care, food, and cosmetic uses

Sorbitol often is used in modern cosmetics as a humectant and thickener. It is also used in mouthwash and toothpaste. Some transparent gels can be made only with sorbitol, because of its high refractive index.

Sorbitol is used as a cryoprotectant additive (mixed with sucrose and sodium polyphosphates) in the manufacture of surimi, a processed fish paste. It is also used as a humectant in some cigarettes.

Beyond its use as a sugar substitute in reduced-sugar foods, sorbitol is also used as a humectant in cookies and low-moisture foods like peanut butter and fruit preserves. In baking, it is also valuable because it acts as a plasticizer, and slows down the staling process.

Miscellaneous uses

A mixture of sorbitol and potassium nitrate has found some success as an amateur solid rocket fuel. It has similar performance to sucrose-based rocket candy, but is easier to cast, less hygroscopic and does not caramelize.

Sorbitol is identified as a potential key chemical intermediate for production of fuels from biomass resources. Carbohydrate fractions in biomass such as cellulose undergo sequential hydrolysis and hydrogenation in the presence of metal catalysts to produce sorbitol. Complete reduction of sorbitol opens the way to alkanes, such as hexane, which can be used as a biofuel. Hydrogen required for this reaction can be produced by aqueous phase catalytic reforming of sorbitol.

19 C₆H₁₄O₆ → 13 C₆H₁₄ + 36 CO₂ + 42 H₂O

The above chemical reaction is exothermic, and 1.5 moles of sorbitol generate approximately 1 mole of hexane. When hydrogen is co-fed, no carbon dioxide is produced.

Sorbitol based polyols are used in the production of polyurethane foam for the construction industry.

It is also added after electroporation of yeasts in transformation protocols, allowing the cells to recover by raising the osmolarity of the medium.

Medical importance

Aldose reductase is the first enzyme in the sorbitol-aldose reductase pathway responsible for the reduction of glucose to sorbitol, as well as the reduction of galactose to galactitol. Too much sorbitol trapped in retinal cells, the cells of the lens, and the Schwann cells that myelinate peripheral nerves, is a frequent result of long-term hyperglycemia that accompanies poorly controlled diabetes. This can damage these cells, leading to retinopathy, cataracts and peripheral neuropathy, respectively.

Sorbitol is fermented in the colon and produces short-chain fatty acids, which are beneficial to overall colon health.

Potential adverse effects

Sorbitol may cause allergic reactions in some people. Common side effects from use as a laxative are stomach cramps, vomiting, diarrhea or rectal bleeding.

Compendial status

References

publications.iupac.org/pac/1996/pdf/6810x1919.pdf
^ Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
"Sorbitol_msds".
^ Teo G, Suzuki Y, Uratsu SL, Lampinen B, Ormonde N, Hu WK, Dejong TM, Dandekar AM (2006). "Silencing leaf sorbitol synthesis alters long-distance partitioning and apple fruit quality". Proceedings of the National Academy of Sciences of the United States of America. 103 (49): 18842–7. Bibcode:2006PNAS..10318842T. doi:10.1073/pnas.0605873103. PMC 1693749. PMID 17132742.
Kearsley, M. W.; Deis, R. C. Sorbitol and Mannitol. In Sweeteners and Sugar Alternatives in Food Technology; Ames: Oxford, 2006; pp 249-249-261.
^ "Sorbitol". Drugs.com. 23 November 2021. Retrieved 8 July 2022.
"Reduction of Glucose". butane.chem.uiuc.edu. Archived from the original on 2017-09-25. Retrieved 2017-10-03.
Sugar substitute
Tsuneyuki Oku and Sadako Nakamura (2002). "Digestion, absorption, fermentation, and metabolism of functional sugar substitutes and their available energy" (PDF). Pure Appl. Chem. 74 (7): 1253–1261. doi:10.1351/pac200274071253.
Campbell, Farrell (2011). Biochemistry (Seventh ed.). Brooks/Cole. ISBN 978-1-111-42564-7.
Hayes C (October 2001). "The effect of non-cariogenic sweeteners on the prevention of dental caries: a review of the evidence". Journal of Dental Education. 65 (10): 1106–1109. doi:10.1002/j.0022-0337.2001.65.10.tb03457.x. ISSN 0022-0337. PMID 11699985.
Nicolas GG, Lavoie MC (January 2011). "". Canadian Journal of Microbiology. 57 (1): 1–20. doi:10.1139/w10-095. ISSN 1480-3275. PMID 21217792.
Nelson, Cox (2005). Lehninger Principles of Biochemistry (Fourth ed.). New York: W. H. Freeman. ISBN 0-7167-4339-6.
"sorbitol". Cancer Drug Guide. American Cancer Society. Archived from the original on 2007-06-30.
Lederle FA (1995). "Epidemiology of constipation in elderly patients. Drug utilisation and cost-containment strategies". Drugs & Aging. 6 (6): 465–9. doi:10.2165/00002512-199506060-00006. PMID 7663066. S2CID 43386314.
Wells JG, Davis BR, Wachsmuth IK, et al. (September 1983). "Laboratory investigation of hemorrhagic colitis outbreaks associated with a rare Escherichia coli serotype". Journal of Clinical Microbiology. 18 (3): 512–20. doi:10.1128/JCM.18.3.512-520.1983. PMC 270845. PMID 6355145. The organism does not ferment sorbitol; whereas 93% of E. coli of human origin are sorbitol positive
Rugolotto S, Gruber M, Solano PD, Chini L, Gobbo S, Pecori S (April 2007). "Necrotizing enterocolitis in a 850 gram infant receiving sorbitol-free sodium polystyrene sulfonate (Kayexalate): clinical and histopathologic findings". J Perinatol. 27 (4): 247–9. doi:10.1038/sj.jp.7211677. PMID 17377608.
"Kayexalate (sodium polystyrene sulfonate) powder". fda.gov. Retrieved 12 July 2015.
"Home – Catalent". catalent.com. Retrieved 12 July 2015.
"Sorbitol 70%". bttcogroup.in. Archived from the original on 10 July 2020. Retrieved 12 July 2015.
Medina J, Garrote R (2002). "The effect of two cryoprotectant mixtures on frozen surubí surimi". Brazilian Journal of Chemical Engineering. 19 (4): 419–424. doi:10.1590/S0104-66322002000400010. ISSN 0104-6632.
"Gallaher Group". gallaher-group.com. Archived from the original on 27 December 2008. Retrieved 12 July 2015.
^ Chemical and functional properties of food saccharides. Tomasik, Piotr. Boca Raton: CRC Press. 2004. ISBN 9780203495728. OCLC 317752036.{{cite book}}: CS1 maint: others (link)
Nakka R. "KNSB Propellant". nakka-rocketry.net. Retrieved 12 July 2015.
Metzger JO (2006). "Production of Liquid Hydrocarbons from Biomass". Angewandte Chemie International Edition. 45 (5): 696–698. doi:10.1002/anie.200502895. PMID 16374789.
Shrotri A, Tanksale, Akshat, Beltramini, Jorge Norberto, Gurav, Hanmant, Chilukuri, Satyanarayana V. (2012). "Conversion of cellulose to polyols over promoted nickel catalysts". Catalysis Science & Technology. 2 (9): 1852–1858. doi:10.1039/C2CY20119D.
Tanksale A, Beltramini, Jorge Norberto, Lu, GaoQing Max (2010). "A review of catalytic hydrogen production processes from biomass". Renewable and Sustainable Energy Reviews. 14 (1): 166–182. Bibcode:2010RSERv..14..166T. doi:10.1016/j.rser.2009.08.010.
Nishikawa T, Edelstein D, Du XL, Yamagishi S, Matsumura T, Kaneda Y, Yorek MA, Beebe D, et al. (2000). "Normalizing mitochondrial superoxide production blocks three pathways of hyperglycaemic damage". Nature. 404 (6779): 787–90. Bibcode:2000Natur.404..787N. doi:10.1038/35008121. PMID 10783895. S2CID 4426750.
Islam MS, Sakaguchi E (2006). "Sorbitol-based osmotic diarrhea: Possible causes and mechanism of prevention investigated in rats". World Journal of Gastroenterology. 12 (47): 7635–7641. doi:10.3748/wjg.v12.i47.7635. PMC 4088045. PMID 17171792.
The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". Archived from the original on 5 July 2010. Retrieved 6 July 2009.
Sigma Aldrich. "D-Sorbitol". Retrieved 15 February 2022.
European Pharmacopoeia. "Index, Ph Eur" (PDF). Archived from the original (PDF) on 20 July 2011. Retrieved 6 July 2009.
British Pharmacopoeia (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 6 July 2009.
National Institute of Health Sciences (2016). "The Japanese Pharmacopoeia, Seventeenth Edition" (PDF). Archived from the original (PDF) on 4 March 2018. Retrieved 17 August 2018.

External links

Media related to Sorbitol at Wikimedia Commons

Alcohols

By consumption

Alcohols found in alcoholic drinks	1-Propanol 2-Methyl-1-butanol Ethanol Isoamyl alcohol Isobutanol Phenethyl alcohol tert-Amyl alcohol tert-Butyl alcohol Tryptophol
Medical alcohol	Ethchlorvynol Methylpentynol Methanol poisoning Ethanol
Toxic alcohols	Isopropyl alcohol Methanol

Primary
alcohols (1°)

Methanol	4-Methylcyclohexanemethanol Aminomethanol Cyclohexylmethanol Methoxymethanol Methylazoxymethanol Trifluoromethanol
Ethanol	1-Aminoethanol 2,2,2-Trichloroethanol 2,2,2-Trifluoroethanol 2-(2-Ethoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-(2-Methoxyethoxy)ethanol 2-Butoxyethanol 2-Chloroethanol 2-Ethoxyethanol 2-Fluoroethanol 2-Mercaptoethanol 2-Methoxyethanol Aminoethylethanolamine Diethylethanolamine Dimethylethanolamine Ethanol Ethanolamine N,N-Diisopropylaminoethanol N-Methylethanolamine Phenoxyethanol Tribromoethanol
Butanol	2-Methyl-1-butanol Isobutanol n-Butanol
Straight-chain saturated C₁ — C₉	Methanol Ethanol 1-Propanol 1-Butanol 1-Pentanol 1-Hexanol 1-Heptanol 1-Octanol (capryl) 1-Nonanol (pelargonic)
Straight-chain saturated C₁₀ — C₁₉	1-Decanol (capric) 1-Undecanol (hendecyl) 1-Dodecanol (lauryl) 1-Tridecanol 1-Tetradecanol (myristyl) 1-Pentadecanol 1-Hexadecanol (cetyl / palmityl) 1-Heptadecanol 1-Octadecanol (stearyl) 1-Nonadecanol
Straight-chain saturated C₂₀ — C₂₉	1-Icosanol (arachidyl) 1-Heneicosanol 1-Docosanol (behenyl) 1-Tricosanol 1-Tetracosanol (lignoceryl) 1-Pentacosanol 1-Hexacosanol (ceryl) 1-Heptacosanol 1-Octacosanol (cluytyl / montanyl) 1-Nonacosanol
Straight-chain saturated C₃₀ — C₃₉	1-Triacontanol (melissyl / myricyl) 1-Hentriacontanol 1-Dotriacontanol (lacceryl) 1-Tritriacontanol 1-Tetratriacontanol (geddyl) 1-Pentatriacontanol 1-Hexatriacontanol 1-Heptatriacontanol 1-Octatriacontanol 1-Nonatriacontanol
Straight-chain saturated C₄₀ — C₄₉	1-Tetracontanol 1-Hentetracontanol 1-Dotetracontanol 1-Tritetracontanol 1-Tetratetracontanol 1-Pentatetracontanol 1-Hexatetracontanol 1-Heptatetracontanol 1-Octatetracontanol 1-Nonatetracontanol

Secondary
alcohols (2°)

Propylene glycol methyl ether

Tertiary
alcohols (3°)

Hydric alcohols

Monohydric alcohols	Methanol (C₁) Ethanol (C₂) Isopropanol (C₃) 1-Butanol (C₄) 1-Pentanol (C₅) Cetyl alcohol (C₁₆)
Dihydric alcohols	Ethylene glycol Propylene glycol
Trihydric alcohols	Glycerol
Polyhydric alcohols (sugar alcohols)	Pentaerythritol Ethylene glycol (C₂) Glycerol, Propylene glycol (C₃) Erythritol, Threitol (C₄) Xylitol (C₅) Mannitol, Sorbitol (C₆) Volemitol (C₇)

Amyl alcohols

Aromatic alcohols

Saturated
fatty alcohols

Branched and
unsaturated
fatty alcohols

Sugar alcohols

C₁ — C₇	Methylene glycol (C₁) Ethylene glycol (C₂) Glycerol (C₃) Erythritol (C₄) Threitol (C₄) Arabitol (C₅) Ribitol (C₅) Xylitol (C₅) Mannitol (C₆) Sorbitol (C₆) Galactitol (C₆) Iditol (C₆) Volemitol (C₇)
Deoxy sugar alcohols	Fucitol
Cyclic sugar alcohols	Inositol
Glycylglycitols	Maltitol Lactitol Isomalt Maltotriitol Maltotetraitol Polyglycitol

Terpene alcohols

Monoterpene alcohols	Borneol Citronellol Geraniol Linalool Menthol Nerol Rhodinol Terpineol
Sesquiterpene alcohols	Bisabolol Farnesol Nerolidol Patchoulol
Diterpene alcohols	Phytol

Dialcohols

Trialcohols

Glycerol

Sterols

Fluoroalcohols

Preparations

Reactions

Category

v t e Blood substitutes and perfusion solutions (B05)
Blood and related products (B05A)	Serum albumin Dextran Gelatin agents Hemoglobin crosfumaril Hemoglobin raffimer Hydroxyethyl starch Erythrocytes Thrombocytes Blood plasma Stem cells from umbilical cord blood
Intravenous solutions (B05B)	Amino acids Lipid emulsions Carbohydrates Protein hydrolysates Electrolytes Trometamol Mannitol Carbamide
Irrigating solutions (B05C)	Cetylpyridinium Chlorhexidine Nitrofural Sulfamethizole Taurolidine Mandelic acid Noxytiolin Ethacridine lactate Neomycin Sodium chloride Sodium citrate Magnesium citrate Sodium bicarbonate Glucose Sorbitol Glycine Mannitol
Others (B05D, B05X)	Peritoneal dialysis solutions Potassium chloride Sodium bicarbonate Sodium chloride Ammonium chloride Magnesium sulfate Potassium phosphate Calcium chloride Sodium acetate Sodium phosphate Magnesium phosphate Magnesium chloride Zinc chloride Hydrochloric acid Sodium glycerophosphate Potassium lactate Cardioplegia solutions Potassium acetate Arginine Alanyl glutamine Lysine

v t e Consumer food safety
Adulterants, food contaminants	3-MCPD Aldicarb Antibiotic use in livestock Cyanide Formaldehyde HGH controversies Lead poisoning Melamine Mercury in fish Sudan I
Food additives	Flavorings Monosodium glutamate (MSG) Salt Sugar High-fructose corn syrup Vegetable oil controversy
Intestinal parasites, parasitic disease	Amoebiasis Anisakiasis Cryptosporidiosis Cyclosporiasis Diphyllobothriasis Enterobiasis Fasciolopsiasis Fasciolosis Giardiasis Gnathostomiasis Paragonimiasis Toxocariasis Toxoplasmosis Trichinosis Trichuriasis
Microorganisms	Botulism Campylobacter jejuni Clostridium perfringens Cronobacter Enterovirus Escherichia coli O104:H4 Escherichia coli O157:H7 Hepatitis A Hepatitis E Listeria Norovirus Rotavirus Salmonella Shigatoxigenic and verotoxigenic E. coli Vibrio cholerae
Pesticides	Chlorpyrifos DDT Lindane Malathion Methamidophos
Preservatives	Benzoic acid Ethylenediaminetetraacetic acid (EDTA) Sodium benzoate
Sugar substitutes	Acesulfame potassium Aspartame controversy Saccharin Sodium cyclamate Sorbitol Sucralose
Toxins, poisons, environment pollution	Aflatoxin Arsenic contamination of groundwater Benzene in soft drinks Bisphenol A Dieldrin Diethylstilbestrol Dioxin Mycotoxins Nonylphenol Shellfish poisoning
Food fraud	Bread Breast milk Egg Olive oil Prawn Seafood Shrimp Tea Wine
Food processing	4-Hydroxynonenal Acid-hydrolyzed vegetable protein Acrylamide Food additives Food irradiation Heterocyclic amines Modified starch Nitrosamines Polycyclic aromatic hydrocarbon Shortening Trans fat Variant Creutzfeldt–Jakob disease Water fluoridation controversy
Food contamination incidents	Devon colic Swill milk scandal Esing Bakery incident 1858 Bradford sweets poisoning 1900 English beer poisoning Morinaga Milk arsenic poisoning incident Minamata disease 1959 Moroccan oil poisoning disaster [ar] 1971 Iraq poison grain disaster Toxic oil syndrome 1985 Austrian diethylene glycol wine scandal United Kingdom BSE outbreak Australian meat substitution scandal Jack in the Box E. coli outbreak 1996 Odwalla E. coli outbreak 2006 North American E. coli outbreaks ICA meat repackaging controversy 2008 Canada listeriosis outbreak 2008 Chinese milk scandal 2008 Irish pork crisis 2008 United States salmonellosis outbreak 2011 Germany E. coli outbreak 2011 United States listeriosis outbreak Bihar school meal poisoning 2013 horse meat scandal 2015 Mozambique funeral beer poisoning 2017 Brazil Operation Weak Meat 2017–2018 South African listeriosis outbreak 2018 Australian strawberry contamination 2024 United Kingdom Shigatoxigenic E. coli outbreak Kobayashi red yeast rice scandal Food safety incidents in China Food safety incidents in Taiwan Foodborne illness outbreaks death toll United States
Regulation, standards, watchdogs	Acceptable daily intake E number Food labeling regulations Food libel laws Food safety in Australia International Food Safety Network ISO 22000 Nutrition facts label Organic certification Quality Assurance International United Kingdom food information regulations
Institutions	Centre for Food Safety (Hong Kong) European Food Safety Authority Food and Drug Administration Food Information and Control Agency (Spain) Food Standards Agency (United Kingdom) Institute for Food Safety and Health International Food Safety Network Ministry of Food and Drug Safety (South Korea) Spanish Agency for Food Safety and Nutrition
Related topics	Curing (food preservation) Food and drink prohibitions Food marketing Food politics Food preservation Food quality Genetically modified food Conspiracy theories
Food portal Drink portal Category Commons Cookbook WikiProject

Diagnostic agents (V04)

Digestive system

Diabetes	Glucose Tolbutamide
Fat absorption	Vitamin A concentrates
Bile duct patency	Ceruletide Magnesium sulfate Sincalide Sorbitol
Liver functional capacity	Galactose Sulfobromophthalein
Gastric secretion	Betazole Caffeine and sodium benzoate Cation exchange resins Histamine phosphate Methylthioninium chloride Pentagastrin
Exocrine pancreatic function	Bentiromide Pancreozymin cholecystokinin Secretin

Endocrine system

Pituitary function	cortisol Corticorelin Metyrapone GH Pralmorelin Sermorelin Somatorelin
Thyroid function	Protirelin Thyrotropin
Fertility disturbances	Gonadorelin

Tuberculosis

Tuberculin

Renal function

v t e Metabolism: carbohydrate metabolism fructose and galactose enzymes
Fructose / Fructolysis	Hepatic fructokinase Aldolase B Triokinase
Sorbitol	Sorbitol dehydrogenase Aldose reductase
Galactose / Galactolysis	Galactokinase Galactose-1-phosphate uridylyltransferase/UDP-glucose 4-epimerase Aldose reductase Galactose mutarotase
Lactose	Lactose synthase Lactase
Mannose	Mannose phosphate isomerase

v t e Drugs for constipation (laxatives and cathartics) (A06)
Stool softeners	Docusate
Stimulant laxatives	Bisacodyl Bisoxatin Cascara Castor oil Dantron Oxyphenisatine Phenolphthalein Senna glycosides Sodium picosulfate
Bulk-forming laxatives	Dietary fiber Ethulose Ispaghula Methylcellulose Polycarbophil calcium Sterculia Triticum Syrup of figs
Lubricant laxatives	Liquid paraffin Mineral oil
Osmotic laxatives	Lactitol Lactulose Laminarid Magnesium carbonate Magnesium citrate Magnesium hydroxide (milk of magnesia) Magnesium oxide Magnesium peroxide Magnesium sulfate Mannitol Pentaerythritol Polyethylene glycol (macrogol) Sodium phosphate Sodium sulfate Sodium tartrate Sorbitol
Enemas	Bisacodyl Dantron Glycerol Oil Sodium laurilsulfate Sodium lauryl sulfoacetate Sodium phosphate Sorbitol
Opioid antagonists	Naloxone (Oxycodone/naloxone) PAMORAs Alvimopan Axelopran Bevenopran Methylnaltrexone Naldemedine Naloxegol
Others	Linaclotide Lubiprostone Oxyphenisatine Plecanatide Prucalopride Tegaserod Tenapanor Ulimorelin

Categories: