Caprylic acid: Difference between revisions

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			{{not to be confused\|Caproic acid\|Capric acid}}
	{{chembox
			{{Short description\|Fatty acid (CH<sub>3</sub>−(CH<sub>2</sub>)<sub>6</sub>−COOH)}}
	\| Watchedfields = changed
			{{Chembox
	\| verifiedrevid = 414046263
			\|Watchedfields = changed
	\| ImageFile = Caprylic acid.svg
			\|verifiedrevid = 443496721
	\| ImageSize = 200px
			\|ImageFile = Caprylic acid.svg
	\| ImageName = Skeletal formula
			\|ImageName = Skeletal formula
	\| ImageFile1 = Caprylic-acid-3D-balls.png
			\|ImageFile1 = Caprylic-acid-3D-balls.png
	\| ImageSize1 = 200px
	\| ImageName1 = Ball-and-stick model		\|ImageName1 = Ball-and-stick model
	\| ~~IUPACName~~ = ~~octanoic~~ acid		\|PIN = Octanoic acid
	\| OtherNames = C8:0 (])		\|OtherNames = 1-Heptanecarboxylic acid<br />Octylic acid<br />Octoic acid<br />C8:0 (]s)
	\| Section1 = {{Chembox Identifiers		\|Section1 = {{Chembox Identifiers
			\|IUPHAR_ligand = 4585
	\| UNII_Ref = {{fdacite\|correct\|FDA}}
			\|UNII_Ref = {{fdacite\|correct\|FDA}}
	\| UNII = OBL58JN025
	\| KEGG_Ref = {{keggcite\|correct\|kegg}}		\|UNII = OBL58JN025
			\|KEGG_Ref = {{keggcite\|correct\|kegg}}
	\| KEGG = D05220		\|KEGG = D05220
	\| InChI = 1/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)		\|InChI = 1/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
	\| InChIKey = WWZKQHOCKIZLMA-UHFFFAOYAH		\|InChIKey = WWZKQHOCKIZLMA-UHFFFAOYAH
	\| ChEMBL_Ref = {{ebicite\|correct\|EBI}}		\|ChEMBL_Ref = {{ebicite\|correct\|EBI}}
	\| ChEMBL = 324846		\|ChEMBL = 324846
	\| StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}		\|StdInChI_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChI = 1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)		\|StdInChI = 1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
	\| StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}		\|StdInChIKey_Ref = {{stdinchicite\|correct\|chemspider}}
	\| StdInChIKey = WWZKQHOCKIZLMA-UHFFFAOYSA-N		\|StdInChIKey = WWZKQHOCKIZLMA-UHFFFAOYSA-N
	\| CASNo_Ref = {{cascite\|correct\|CAS}}		\|CASNo_Ref = {{cascite\|correct\|CAS}}
	\| CASNo = 124-07-2		\|CASNo = 124-07-2
	\| PubChem = 379		\|PubChem = 379
	\| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}		\|ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}}
	\| ChemSpiderID = 370		\|ChemSpiderID = 370
			\|DrugBank_Ref = {{drugbankcite\|correct\|drugbank}}
	\| DrugBank = DB04519
	\| ~~ChEBI~~ = ~~28837~~		\|DrugBank = DB04519
			\|ChEBI_Ref = {{ebicite\|correct\|EBI}}
	\| SMILES = CCCCCCCC(=O)O
			\|ChEBI = 28837
	\| IUPACName = Octanoic acid
			\|SMILES = CCCCCCCC(=O)O
	}}
			\|EINECS = 204-677-5
	\|Section2= {{Chembox Properties
			}}
	\| Formula=C<sub>8</sub>H<sub>16</sub>O<sub>2</sub>
			\|Section2 = {{Chembox Properties
	\| MolarMass=144.21 g/mol
			\|C = 8 \| H = 16 \| O = 2
	\| Appearance=Oily colorless liquid
			\|MolarMassUnit = g/mol
	\| Density=0.910 g/cm<sup>3</sup><ref name=Merck/>
			\|Appearance = Oily colorless liquid
	\| MeltingPtC=16.7
			\|Odor = Faint, fruity-acid; irritating
	\| Melting_notes = <ref name="lexicon">{{cite journal \|year=2001 \|title=Lexicon of lipid nutrition (IUPAC Technical Report) \|journal=Pure and Applied Chemistry \|volume=73 \|issue=4 \|pages=685–744 \|url=http://iupac.org/publications/pac/73/4/0685/ \|doi=10.1351/pac200173040685 \|last1=Beare-Rogers \|first1=J. \|last2=Dieffenbacher \|first2=A. \|last3=Holm \|first3=J.V. }}</ref>
			\|Density = 0.910 g/cm<sup>3</sup><ref name=Merck/>
	\| BoilingPtC=239.7
			\|MeltingPtC = 16.7
	\| Boiling_notes = <ref name=Merck>{{Merck12th}}</ref>
			\|MeltingPt_ref = <ref name="lexicon">{{cite journal \|year=2001 \|title=Lexicon of lipid nutrition (IUPAC Technical Report) \|journal=Pure and Applied Chemistry \|volume=73 \|issue=4 \|pages=685–744 \|doi=10.1351/pac200173040685 \|doi-access=free \|last1=Beare-Rogers \|first1=J. \|last2=Dieffenbacher \|first2=A. \|last3=Holm \|first3=J.V. \|s2cid=84492006 }}</ref>
	\| Solubility= 0.68 g/100 mL<ref name=Merck/>
			\|BoilingPtC = 239.7
	\| pKa=4.89<ref name=crc>{{cite book \| author=Lide, D. R. (Ed.) \| title=CRC Handbook of Chemistry and Physics (70th Edn.) \| publisher=Boca Raton (FL):CRC Press \| year=1990}}</ref> \|\| 1.055<ref>at 2.06–2.63 K</ref> \|\| 1.53<ref>at −191 °C</ref>
			\|BoilingPt_ref = <ref name=Merck>{{Merck12th}}</ref>
	}}
			\|Solubility = 0.068 g/100 mL<ref name=Merck/>
	\|Section3= {{Chembox Hazards
			\|SolubleOther = Soluble in ], ], ], ], ], ]
	\| MainHazards=
			\|pKa = {{ubli
	\| FlashPt=
			\|4.89<ref name=crc>{{cite book \| author=Lide, D.R. (Ed.) \| title=CRC Handbook of Chemistry and Physics (70th Edn.) \| publisher=Boca Raton (FL):CRC Press \| year=1990}}</ref>
	\| Autoignition=
			\|1.055 (2.06–2.63 K)
	\| LD50 = 10.08 g/kg (orally in rats)<ref name=Merck/>
			\|1.53 (−191 °C)
	}}
			}}
			\|LogP = 3.05
			\|RefractIndex = 1.4285
			\|VaporPressure = 0.25 Pa
			\|MagSus = −101.60·10<sup>−6</sup> cm<sup>3</sup>/mol
			}}
			\|Section3 = {{Chembox Thermochemistry
			\|DeltaHf = −636 kJ/mol
			\|HeatCapacity = 297.9 J/K·mol
			}}
			\|Section4 = {{Chembox Hazards
			\|FlashPtC = 130
			\|AutoignitionPtC = 440
			\|NFPA-H = 3 \| NFPA-F = 0 \| NFPA-R = 1 \| NFPA-S = COR
			\|LD50 = 10.08 g/kg (orally in rats)<ref name=Merck/>
			\|GHSPictograms = {{GHS05}}<ref name="sigma">{{Sigma-Aldrich\| id= w279927\|name=Octanoic acid\|accessdate=2022-08-11}}</ref>
			\|GHSSignalWord = Danger
			\|HPhrases = {{H-phrases\|314}}
			\|PPhrases = {{P-phrases\|264\|280\|301+330+331\|303+361+353\|304+340+310\|305+351+338+310\|363\|405\|501}}
			}}
			\|Section5 = {{Chembox Related
			\|OtherCompounds = ], ]
			}}
	}}		}}

			'''Caprylic acid''' ({{ety\|la\|]\|goat}}), also known under the ] '''octanoic acid''' or '''C8 Acid''', is a ], ] (MCFA). It has the structural formula {{chem2\|H3C\s(CH2)6\s]}}, and is a colorless oily liquid that is minimally ] in water with a slightly unpleasant rancid-like smell and taste.<ref name=Merck/> ] and ]s of octanoic acid are known as '''octanoates''' or '''caprylates'''. The name of the related ] is '''octanoyl''', '''capryloyl''', or '''caprylyl'''.<ref>{{cite web\|url=https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:25650\|title=CHEBI:25650 - octanoyl group\|publisher=Chemical Entities of Biological Interest (ChEBI)\|date=23 November 2010\|access-date=4 July 2024}}</ref> It is a common industrial chemical, which is produced by oxidation of the ].<ref name=Ullmann>{{Ullmann\|first1=Wilhelm\|last1=Riemenschneider\|title=Carboxylic Acids, Aliphatic\|year=2002\|doi=10.1002/14356007.a05_235}}</ref> Its compounds are found naturally in the ] of various mammals and as a minor constituent of ] and ].<ref name="lexicon" />
	'''Caprylic acid''' is the common name for the eight-carbon saturated ] known by the systematic name '''octanoic acid'''. It is found naturally in the ] of various mammals, and it is a minor constituent of ] and ].<ref name="lexicon" /> It is an oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste.<ref name=Merck/>

	Two other acids are named after ]s: ] (C6) and ] (C10). ~~Along~~ ~~with~~ ~~caprylic~~ ~~acid~~ ~~these~~ ~~total~~ 15% in goat milk fat.		Two other acids are named after ]s via the Latin word '']'': ] (C6) and ] (C10). Together, these three fatty acids comprise 15% of the fatty acids in ] fat.

	==Uses==		==Uses==
	Caprylic acid is used commercially in the production of ]s used in perfumery and also in the manufacture of dyes.		Caprylic acid is used commercially in the production of ]s used in perfumery and also in the manufacture of dyes.{{cn\|date=June 2022}}

			Caprylic acid is an antimicrobial pesticide used as a food contact surface sanitizer in commercial food handling establishments on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants. It is also used as disinfectant in health care facilities and public places. In addition, caprylic acid is used as an algicide, bactericide, fungicide, and herbicide in nurseries, greenhouses, garden centers, and interiors, and on ornamentation. Products containing caprylic acid are formulated as soluble concentrate/liquids and ready-to-use liquids.<ref>EPA - Antimicrobials Division. .</ref>
	Caprylic acid is also used in the treatment of some ]l infections. Due to its relatively short chain length it has no difficulty in penetrating fatty cell wall membranes, hence its effectiveness in combating certain lipid-coated bacteria, such as '']'' and various species of '']''.<ref>{{cite journal \| doi = 10.3168/jds.S0022-0302(05)73033-2 \| author = Nair MK, Joy J, Vasudevan P, Hinckley L, Hoagland TA, Venkitanarayanan KS \| title = Antibacterial effect of caprylic acid and monocaprylin on major bacterial mastitis pathogens \| journal = J Dairy Sci \| year = 2005 \| month = Oct \| volume = 88 \| issue = 10 \| pages = 3488–95 \| pmid = 16162522}}</ref>

			Caprylic acid plays an important role in the body's regulation of energy input and output, a function which is performed by the hormone ]. The sensation of hunger is a signal that the body requires an input of energy in the form of food consumption. Ghrelin stimulates hunger by triggering ] in the ]. In order to activate these receptors, ghrelin must undergo a process called ] in which it acquires an ], and caprylic acid provides this by linking at a specific ] site on ghrelin molecules. Other ]s in the same position have similar effects on hunger.{{cn\|date=March 2021}}
	Caprylic acid is an antimicrobial pesticide used as a food contact surface sanitizer in commercial food handling establishments on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants. It is also used as disinfectant in health care facilities, schools/colleges, animal care/veterinary facilities, industrial facilities, office buildings, recreational facilities, retail and wholesale establishments, livestock premises, restaurants, and hotels/motels. In addition, caprylic acid is used as an algaecide, bactericide, and fungicide in nurseries, greenhouses, garden centers, and interiorscapes on ornamentals. Products containing caprylic acid are formulated as soluble concentrate/liquids and ready-to-use liquids.<ref>EPA - Antimicrobials Division - www.regulations.gov - Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid. </ref>

			The ] of caprylic acid is used in the synthesis of ].<ref name=savu2000>{{cite encyclopedia \|doi=10.1002/0471238961.0612211519012221.a01 \|chapter=Fluorinated Higher Carboxylic Acids \|encyclopedia=] \|year=2000 \|last1=Savu \|first1=Patricia M. \|page=1 \|isbn=978-0-471-23896-6}}</ref>
	Caprylic acid must be covalently linked to the ] residue at the 3-position of ], specifically, it must acylate the ], for ] to have its hunger-stimulating action on the feeding centers of the ], though other fatty acids may have similar effects.{{Clarify\|date=August 2009}}

			===Dietary uses===
	The ] is used to measure ].
			{{see also\|Medium-chain triglyceride#Dietary relevance}}

			Caprylic acid is taken as a ]. In the body, caprylic acid would be found as octanoate, or unprotonated caprylic acid.<ref>{{Cite web\|url=https://pubchem.ncbi.nlm.nih.gov/compound/379\|title=Octanoic acid\|last=PubChem\|website=pubchem.ncbi.nlm.nih.gov\|language=en\|access-date=2019-05-15}}</ref>

			Some studies have shown that medium-chain triglycerides (MCTs) can help in the process of excess calorie burning, and thus ];<ref>{{cite journal\| title = Medium-chain triglycerides\|author1=B. Martena \|author2=M. Pfeuffer \|author3=J. Schrezenmeir \|journal= International Dairy Journal \|volume= 16\| issue= 11\|year= 2006\| pages =1374–1382 \|doi=10.1016/j.idairyj.2006.06.015\|pmc=2020023}}</ref><ref>{{Cite journal
			\| last1 = Takeuchi
			\| first1 = H
			\| last2 = Sekine
			\| first2 = S
			\| last3 = Kojima
			\| first3 = K
			\| last4 = Aoyama
			\| first4 = T
			\| title = The application of medium-chain fatty acids: edible oil with a suppressing effect on body fat accumulation
			\| journal = Asia Pacific Journal of Clinical Nutrition
			\| volume = 17
			\| pages = 320–3
			\| year = 2008
			\| issue = Suppl 1
			\| pmid = 18296368
			}}</ref><ref>{{Cite journal
			\| last1 = St-Onge
			\| first1 = MP
			\| last2 = Jones
			\| first2 = PJ
			\| title = Physiological effects of medium-chain triglycerides: potential agents in the prevention of obesity
			\| journal = The Journal of Nutrition
			\| volume = 132
			\| issue = 3
			\| pages = 329–32
			\| year = 2002
			\| pmid = 11880549
			\| doi = 10.1093/jn/132.3.329
			\| doi-access = free
			}}</ref><ref>{{Cite journal
			\| last1 = Papamandjaris
			\| first1 = AA
			\| last2 = MacDougall
			\| first2 = DE
			\| last3 = Jones
			\| first3 = PJ
			\| title = Medium chain fatty acid metabolism and energy expenditure: obesity treatment implications
			\| journal = Life Sciences
			\| volume = 62
			\| issue = 14
			\| pages = 1203–15
			\| year = 1998
			\| pmid = 9570335
			\| doi=10.1016/S0024-3205(97)01143-0
			}}</ref><ref name="Clegg">{{Cite journal
			\| last1 = Clegg \| first1 = M. E.
			\| title = Medium-chain triglycerides are advantageous in promoting weight loss although not beneficial to exercise performance
			\| journal = International Journal of Food Sciences and Nutrition
			\| volume = 61
			\| issue = 7
			\| pages = 653–679
			\| year = 2010
			\| pmid = 20367215
			\| doi = 10.3109/09637481003702114

			\| s2cid = 6128370
			}}</ref> however, a systematic review of the evidence concluded that the overall results are inconclusive.<ref>{{Cite journal \| journal = Nutr Hosp \| date = 2012 \| volume = 27 \| issue = 1 \| pages = 103–108 \| doi= 10.3305/nh.2012.27.1.5369 \| title = Influence of the dietary intake of medium chain triglycerides on body composition, energy expenditure and satiety: a systematic review \|vauthors=Rego Costa AC, Rosado EL, Soares-Mota M \| pmid = 22566308}}</ref> Also, interest in MCTs has been shown by endurance athletes and the ] community, but MCTs have not been found to be beneficial to exercise performance.<ref name=Clegg/>

			===Medical uses===
			Caprylic acid has been studied as part of a ] to treat children with ].<ref name=":0" /> Caprylic acid is currently being researched as a treatment for ].<ref name=":0">{{Cite journal\|last1=Voller\|first1=Bernhard\|last2=Lines\|first2=Emily\|last3=McCrossin\|first3=Gayle\|last4=Tinaz\|first4=Sule\|last5=Lungu\|first5=Codrin\|last6=Grimes\|first6=George\|last7=Starling\|first7=Judith\|last8=Potti\|first8=Gopal\|last9=Buchwald\|first9=Peter\|date=2016-02-29\|title=Dose-escalation study of octanoic acid in patients with essential tremor\|journal=Journal of Clinical Investigation\|language=en\|volume=126\|issue=4\|pages=1451–1457\|doi=10.1172/JCI83621\|pmid=26927672\|issn=0021-9738\|pmc=4811161}}</ref><ref>{{Cite journal\|last1=Lowell\|first1=Soren Y.\|last2=Kelley\|first2=Richard T.\|last3=Monahan\|first3=Marika\|last4=Hosbach-Cannon\|first4=Carly Jo\|last5=Colton\|first5=Raymond H.\|last6=Mihaila\|first6=Dragos\|date=2018-12-25\|title=The Effect of Octanoic Acid on Essential Voice Tremor: A Double-Blind, Placebo-Controlled Study: Effect of Octanoic Acid on EVT\|journal=The Laryngoscope\|volume=129\|issue=8\|pages=1882–1890\|language=en\|doi=10.1002/lary.27695\|pmid=30585335\|pmc=6592780}}</ref>

			==See also==
			* ]
			* ]

	==References==		==References==
	{{Reflist}}		{{Reflist}}

			== External links ==

			* – Caprylic Acid: Benefits & Side Effects

	{{Fatty acids}}		{{Fatty acids}}
			{{Authority control}}

	{{DEFAULTSORT:Caprylic Acid}}		{{DEFAULTSORT:Caprylic Acid}}
	]
	]
	]		]
			]

			]
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Latest revision as of 14:31, 4 July 2024

Not to be confused with Caproic acid or Capric acid. Fatty acid (CH₃−(CH₂)₆−COOH)

Caprylic acid
Names
Skeletal formula
Ball-and-stick model
Preferred IUPAC name Octanoic acid
Other names 1-Heptanecarboxylic acid Octylic acid Octoic acid C8:0 (lipid numbers)
Identifiers
CAS Number	124-07-2
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28837
ChEMBL	ChEMBL324846
ChemSpider	370
DrugBank	DB04519
ECHA InfoCard	100.004.253
EC Number	204-677-5
IUPHAR/BPS	4585
KEGG	D05220
PubChem CID	379
UNII	OBL58JN025
CompTox Dashboard (EPA)	DTXSID3021645
InChI InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)Key: WWZKQHOCKIZLMA-UHFFFAOYSA-N InChI=1/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)Key: WWZKQHOCKIZLMA-UHFFFAOYAH
SMILES CCCCCCCC(=O)O
Properties
Chemical formula	C₈H₁₆O₂
Molar mass	144.214 g/mol
Appearance	Oily colorless liquid
Odor	Faint, fruity-acid; irritating
Density	0.910 g/cm
Melting point	16.7 °C (62.1 °F; 289.8 K)
Boiling point	239.7 °C (463.5 °F; 512.8 K)
Solubility in water	0.068 g/100 mL
Solubility	Soluble in alcohol, chloroform, ether, CS₂, petroleum ether, acetonitrile
log P	3.05
Vapor pressure	0.25 Pa
Acidity (pK_a)	4.89 1.055 (2.06–2.63 K) 1.53 (−191 °C)
Magnetic susceptibility (χ)	−101.60·10 cm/mol
Refractive index (n_D)	1.4285
Thermochemistry
Heat capacity (C)	297.9 J/K·mol
Std enthalpy of formation (Δ_fH₂₉₈)	−636 kJ/mol
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P264, P280, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310, P363, P405, P501
NFPA 704 (fire diamond)	3 0 1 COR
Flash point	130 °C (266 °F; 403 K)
Autoignition temperature	440 °C (824 °F; 713 K)
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	10.08 g/kg (orally in rats)
Related compounds
Related compounds	Heptanoic acid, nonanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Y verify (what is ?) Infobox references

Chemical compound

Caprylic acid (from Latin capra 'goat'), also known under the systematic name octanoic acid or C8 Acid, is a saturated fatty acid, medium-chain fatty acid (MCFA). It has the structural formula H₃C−(CH₂)₆−COOH, and is a colorless oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste. Salts and esters of octanoic acid are known as octanoates or caprylates. The name of the related acyl group is octanoyl, capryloyl, or caprylyl. It is a common industrial chemical, which is produced by oxidation of the C8 aldehyde. Its compounds are found naturally in the milk of various mammals and as a minor constituent of coconut oil and palm kernel oil.

Two other acids are named after goats via the Latin word capra: caproic acid (C6) and capric acid (C10). Together, these three fatty acids comprise 15% of the fatty acids in goat milk fat.

Uses

Caprylic acid is used commercially in the production of esters used in perfumery and also in the manufacture of dyes.

Caprylic acid is an antimicrobial pesticide used as a food contact surface sanitizer in commercial food handling establishments on dairy equipment, food processing equipment, breweries, wineries, and beverage processing plants. It is also used as disinfectant in health care facilities and public places. In addition, caprylic acid is used as an algicide, bactericide, fungicide, and herbicide in nurseries, greenhouses, garden centers, and interiors, and on ornamentation. Products containing caprylic acid are formulated as soluble concentrate/liquids and ready-to-use liquids.

Caprylic acid plays an important role in the body's regulation of energy input and output, a function which is performed by the hormone ghrelin. The sensation of hunger is a signal that the body requires an input of energy in the form of food consumption. Ghrelin stimulates hunger by triggering receptors in the hypothalamus. In order to activate these receptors, ghrelin must undergo a process called acylation in which it acquires an acyl group, and caprylic acid provides this by linking at a specific serine site on ghrelin molecules. Other fatty acids in the same position have similar effects on hunger.

The acyl chloride of caprylic acid is used in the synthesis of perfluorooctanoic acid.

Dietary uses

Caprylic acid is taken as a dietary supplement. In the body, caprylic acid would be found as octanoate, or unprotonated caprylic acid.

Some studies have shown that medium-chain triglycerides (MCTs) can help in the process of excess calorie burning, and thus weight loss; however, a systematic review of the evidence concluded that the overall results are inconclusive. Also, interest in MCTs has been shown by endurance athletes and the bodybuilding community, but MCTs have not been found to be beneficial to exercise performance.

Medical uses

Caprylic acid has been studied as part of a ketogenic diet to treat children with intractable epilepsy. Caprylic acid is currently being researched as a treatment for essential tremor.

References

^ Budavari, Susan, ed. (1996). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.). Merck. ISBN 0911910123.
Lide, D.R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.
^ Beare-Rogers, J.; Dieffenbacher, A.; Holm, J.V. (2001). "Lexicon of lipid nutrition (IUPAC Technical Report)". Pure and Applied Chemistry. 73 (4): 685–744. doi:10.1351/pac200173040685. S2CID 84492006.
Sigma-Aldrich Co., Octanoic acid. Retrieved on 2022-08-11.
"CHEBI:25650 - octanoyl group". Chemical Entities of Biological Interest (ChEBI). 23 November 2010. Retrieved 4 July 2024.
Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235. ISBN 978-3-527-30673-2.
EPA - Antimicrobials Division. Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid.
Savu, Patricia M. (2000). "Fluorinated Higher Carboxylic Acids". Kirk-Othmer Encyclopedia of Chemical Technology. p. 1. doi:10.1002/0471238961.0612211519012221.a01. ISBN 978-0-471-23896-6.
PubChem. "Octanoic acid". pubchem.ncbi.nlm.nih.gov. Retrieved 2019-05-15.
B. Martena; M. Pfeuffer; J. Schrezenmeir (2006). "Medium-chain triglycerides". International Dairy Journal. 16 (11): 1374–1382. doi:10.1016/j.idairyj.2006.06.015. PMC 2020023.
Takeuchi, H; Sekine, S; Kojima, K; Aoyama, T (2008). "The application of medium-chain fatty acids: edible oil with a suppressing effect on body fat accumulation". Asia Pacific Journal of Clinical Nutrition. 17 (Suppl 1): 320–3. PMID 18296368.
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External links

Caprylic Acid Benefits – Caprylic Acid: Benefits & Side Effects

v t e Lipids: fatty acids
Saturated	Propionic (C3) Butyric (C4) Valeric (C5) Caproic (C6) Enanthic (C7) Caprylic (C8) Pelargonic (C9) Capric (C10) Undecylic (C11) Lauric (C12) Tridecylic (C13) Myristic (C14) Pentadecylic (C15) Palmitic (C16) Margaric (C17) Stearic (C18) Nonadecylic (C19) Arachidic (C20) Heneicosylic (C21) Behenic (C22) Tricosylic (C23) Lignoceric (C24) Pentacosylic (C25) Cerotic (C26) Carboceric (C27) Montanic (C28) Nonacosylic (C29) Melissic (C30) Hentriacontylic (C31) Lacceroic (C32) Psyllic (C33) Geddic (C34) Ceroplastic (C35) Hexatriacontylic (C36) Heptatriacontanoic (C37) Octatriacontanoic (C38) Nonatriacontanoic (C39) Tetracontanoic (C40)
ω−3 Unsaturated	Octenoic (8:1) Decenoic (10:1) Decadienoic (10:2) Lauroleic (12:1) Laurolinoleic (12:2) Myristovaccenic (14:1) Myristolinoleic (14:2) Myristolinolenic (14:3) Palmitolinolenic (16:3) Palmitidonic (16:4) α-Linolenic (18:3) Stearidonic (18:4) α-Parinaric (18:4) Dihomo-α-linolenic (20:3) Eicosatetraenoic (20:4) Eicosapentaenoic (20:5) Clupanodonic (22:5) Docosahexaenoic (22:6) 9,12,15,18,21-Tetracosapentaenoic (24:5) 6,9,12,15,18,21-Tetracosahexaenoic (24:6)
ω−5 Unsaturated	Myristoleic (14:1) Palmitovaccenic (16:1) α-Eleostearic (18:3) β-Eleostearic (trans-18:3) Punicic (18:3) 7,10,13-Octadecatrienoic (18:3) 9,12,15-Eicosatrienoic (20:3) β-Eicosatetraenoic (20:4)
ω−6 Unsaturated	8-Tetradecenoic (14:1) 12-Octadecenoic (18:1) Linoleic (18:2) Linolelaidic (trans-18:2) γ-Linolenic (18:3) Calendic (18:3) Pinolenic (18:3) Dihomo-linoleic (20:2) Dihomo-γ-linolenic (20:3) Sciadonic (20:3) Arachidonic (20:4) Adrenic (22:4) Osbond (22:5)
ω−7 Unsaturated	Palmitoleic (16:1) Vaccenic (18:1) Rumenic (18:2) Paullinic (20:1) 7,10,13-Eicosatrienoic (20:3)
ω−9 Unsaturated	Oleic (18:1) Elaidic (trans-18:1) Gondoic (20:1) Erucic (22:1) Nervonic (24:1) 8,11-Eicosadienoic (20:2) Mead (20:3)
ω−10 Unsaturated	Sapienic (16:1)
ω−11 Unsaturated	Gadoleic (20:1)
ω−12 Unsaturated	4-Hexadecenoic (16:1) Petroselinic (18:1) 8-Eicosenoic (20:1)

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