| Revision as of 11:24, 15 February 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: ChEMBL KEGG.← Previous edit |
Latest revision as of 14:31, 4 July 2024 edit undoTeaktl17 (talk | contribs)Extended confirmed users18,034 edits →top: + caprylyl, reordered per frequency of use |
| (145 intermediate revisions by 97 users not shown) |
| Line 1: |
Line 1: |
|
|
{{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)}} |
|
| verifiedrevid = 401943095 |
|
|
|
{{Chembox |
|
| ImageFile = Caprylic acid.svg |
|
|
|
|Watchedfields = changed |
|
| ImageSize = 210px |
|
|
|
|verifiedrevid = 443496721 |
|
| ImageName = Skeletal formula |
|
|
| ImageFile1 = Caprylic-acid-3D-balls.png |
|
|ImageFile = Caprylic acid.svg |
|
|
|ImageName = Skeletal formula |
|
| ImageSize1 = 210px |
|
|
|
|ImageFile1 = Caprylic-acid-3D-balls.png |
|
| 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 |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
|
|
|IUPHAR_ligand = 4585 |
|
| UNII = OBL58JN025 |
|
|
|
|UNII_Ref = {{fdacite|correct|FDA}} |
|
| KEGG = D05220 |
|
|
|
|UNII = OBL58JN025 |
|
| InChI = 1/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) |
|
|
|
|KEGG_Ref = {{keggcite|correct|kegg}} |
|
| InChIKey = WWZKQHOCKIZLMA-UHFFFAOYAH |
|
|
| ChEMBL = 324846 |
|
|KEGG = D05220 |
|
|
|InChI = 1/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) |
|
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|
|
|InChIKey = WWZKQHOCKIZLMA-UHFFFAOYAH |
|
| StdInChI = 1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) |
|
|
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
|ChEMBL_Ref = {{ebicite|correct|EBI}} |
|
|
|ChEMBL = 324846 |
|
| StdInChIKey = WWZKQHOCKIZLMA-UHFFFAOYSA-N |
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
|
|StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
|
|
|StdInChI = 1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) |
|
| CASNo = 124-07-2 |
|
|
|
|StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
|
| PubChem = 379 |
|
|
|
|StdInChIKey = WWZKQHOCKIZLMA-UHFFFAOYSA-N |
|
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
|
|
|CASNo_Ref = {{cascite|correct|CAS}} |
|
| ChemSpiderID = 370 |
|
|
|
|CASNo = 124-07-2 |
|
| SMILES = CCCCCCCC(=O)O |
|
|
|
|PubChem = 379 |
|
| IUPACName = Octanoic acid |
|
|
|
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
|
}} |
|
|
|
|ChemSpiderID = 370 |
|
|Section2= {{Chembox Properties |
|
|
|
|DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
|
| Formula=C<sub>8</sub>H<sub>16</sub>O<sub>2</sub> |
|
|
|
|DrugBank = DB04519 |
|
| MolarMass=144.21 g/mol |
|
|
|
|ChEBI_Ref = {{ebicite|correct|EBI}} |
|
| Appearance=Oily colorless liquid |
|
|
|
|ChEBI = 28837 |
|
| Density=0.910 g/cm<sup>3</sup> |
|
|
|
|SMILES = CCCCCCCC(=O)O |
|
| MeltingPt=16.7 °C<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> |
|
|
|
|EINECS = 204-677-5 |
|
| BoilingPtC=237 |
|
|
|
}} |
|
| Solubility= |
|
|
|
|Section2 = {{Chembox Properties |
|
| SolubleOther = 6.31 M <ref></ref> |
|
|
|
|C = 8 | H = 16 | O = 2 |
|
| Solvent = ] |
|
|
|
|MolarMassUnit = g/mol |
|
| 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> |
|
|
|
|Appearance = Oily colorless liquid |
|
}} |
|
|
|
|Odor = Faint, fruity-acid; irritating |
|
|Section3= {{Chembox Hazards |
|
|
|
|Density = 0.910 g/cm<sup>3</sup><ref name=Merck/> |
|
| MainHazards= |
|
|
|
|MeltingPtC = 16.7 |
|
| FlashPt= |
|
|
|
|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> |
|
| Autoignition= |
|
|
|
|BoilingPtC = 239.7 |
|
}} |
|
|
|
|BoilingPt_ref = <ref name=Merck>{{Merck12th}}</ref> |
|
|
|Solubility = 0.068 g/100 mL<ref name=Merck/> |
|
|
|SolubleOther = Soluble in ], ], ], ], ], ] |
|
|
|pKa = {{ubli |
|
|
|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 (2.06–2.63 K) |
|
|
|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. |
|
|
|
|
|
|
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 ].{{clarify|date=October 2010}} |
|
|
|
{{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}} |
|
] |
|
|
] |
|
|
] |
|
] |
|
|
] |
|
|
|
|
|
] |
|
] |
|
|
|
] |
|
] |
|
|
|
] |
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|
|
] |
|