Caprylic acid
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| Other names |
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| Identifiers |
| CAS number |
124-07-2 Y |
| PubChem |
379 |
| ChemSpider |
370 Y |
| UNII |
OBL58JN025 Y |
| EC number |
204-677-5 |
| DrugBank |
DB04519 Y |
| KEGG |
D05220 Y |
| ChEBI |
CHEBI:28837 Y |
| ChEMBL |
ChEMBL324846 Y |
| Jmol-3D images |
Image |
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InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) Y
Key: WWZKQHOCKIZLMA-UHFFFAOYSA-N Y
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InChI=1/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
Key: WWZKQHOCKIZLMA-UHFFFAOYAH
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| Properties |
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Molecular formula
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C8H16O2 |
| Molar mass |
144.21 g/mol |
| Appearance |
Oily colorless liquid |
| Odor |
faint, fruity-acid; irritating |
| Density |
0.910 g/cm3[1] |
| Melting point |
16.7 °C (62.1 °F; 289.8 K)[5] |
| Boiling point |
239.7 °C (463.5 °F; 512.8 K)[1] |
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Solubility in water
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0.068 g/100 mL[1] |
| Solubility |
soluble in alcohol, chloroform, ether, CS2, petroleum ether, acetonitrile |
| log P |
3.05 |
| Vapor pressure |
0.25 Pa |
| Acidity (pKa) |
4.89[2]
1.055[3]
1.53[4]
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Refractive index (nD)
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1.4285 |
| Thermochemistry |
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Specific
heat capacity (C)
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297.9 J/K mol |
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Std enthalpy of
formation (ΔfHo298)
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-636 kJ/mol |
| Hazards |
| NFPA 704 |
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| Flash point |
130 °C (266 °F; 403 K) |
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Autoignition
temperature
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440 °C (824 °F; 713 K) |
| LD50 |
10.08 g/kg (orally in rats)[1] |
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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| Y verify (what is: Y/N?) |
| Infobox references |
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Caprylic acid is the common name for the eight-carbon saturated fatty acid known by the systematic name octanoic acid. Its compounds are found naturally in the milk of various mammals, and as a minor constituent of coconut oil and palm kernel oil.[5] It is an oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste.[1]
Two other acids are named after goats: caproic (C6) and capric (C10). Along with caprylic acid these total 15% 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, 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.[6]
For ghrelin to have a hunger-stimulating action on a hypothalamus, caprylic acid must be linked to a serine residue at the 3-position of ghrelin. To cause hunger, it must acylate an -OH group. Other fatty acids in the same position have similar effects on hunger.
The acid chloride of caprylic acid is used in the synthesis of perfluorooctanoic acid.
Dietary uses
See also: Medium-chain triglyceride § Dietary relevance
Caprylic acid is taken as a dietary supplement.
Some studies have shown that MCTs can help in the process of excess calorie burning, and thus weight loss.[7][8][9][10] MCTs are also seen as promoting fat oxidation and reduced food intake.[11] There has also been interest in MCTs from endurance athletes and the bodybuilding community.[12]
It is believed to suppress fungal infections within the gut, notably candida albicans infection.[citation needed]
References
- ^ a b c d e 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.
- ^ at 2.06–2.63 K
- ^ at −191 °C
- ^ a b 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.
- ^ EPA - Antimicrobials Division. Docket Number; EPA-HQ-OPP-2008-0477 Caprylic (Octanoic) Acid.
- ^ 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.
- ^ 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. edit
- ^ St-Onge, MP; Jones, PJ (2002). "Physiological effects of medium-chain triglycerides: potential agents in the prevention of obesity". The Journal of nutrition 132 (3): 329–32. PMID 11880549. edit
- ^ Papamandjaris, AA; MacDougall, DE; Jones, PJ (1998). "Medium chain fatty acid metabolism and energy expenditure: obesity treatment implications". Life Sciences 62 (14): 1203–15. doi:10.1016/S0024-3205(97)01143-0. PMID 9570335. edit
- ^ Clegg, M. E. (2010). "Medium-chain triglycerides are advantageous in promoting weight loss although not beneficial to exercise performance". International Journal of Food Sciences and Nutrition 61 (7): 653–679. doi:10.3109/09637481003702114. PMID 20367215. edit
- ^ Talbott, Shawn M. and Kerry Hughes. (2006). The Health Professional's Guide to Dietary Supplements. Lippincott Williams & Wilkins. pp. 60–63. ISBN 978-0-7817-4672-4.
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Lipids: fatty acids
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| Saturated |
- VFA: Acetic (C2)
- Propionic acid (C3)
- Butyric (C4)
- Valeric (C5)
- Caproic (C6)
- Enanthic (C7)
- Caprylic (C8)
- Pelargonic (C9)
- Capric (C10)
- Undecylic (C11)
- Lauric (C12)
- Tridecylic (C13)
- Myristic (C14)
- Pentadecanoic (C15)
- Palmitic (C16)
- Margaric (C17)
- Stearic (C18)
- Nonadecylic (C19)
- Arachidic (C20)
- Heneicosylic (C21)
- Behenic (C22)
- Tricosylic (C23)
- Lignoceric (C24)
- Pentacosylic (C25)
- Cerotic (C26)
- Heptacosylic (C27)
- Montanic (C28)
- Nonacosylic (C29)
- Melissic (C30)
- Hentriacontylic (C31)
- Lacceroic (C32)
- Psyllic (C33)
- Geddic (C34)
- Ceroplastic (C35)
- Hexatriacontylic (C36)
- Heptatriacontanoic (C37)
- Octatriacontanoic (C38)
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| ω−3 Unsaturated |
- α-Linolenic (18:3)
- Stearidonic (18:4)
- Eicosapentaenoic (20:5)
- Docosahexaenoic (22:6)
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| ω−6 Unsaturated |
- Linoleic (18:2)
- γ-Linolenic (18:3)
- Dihomo-γ-linolenic (20:3)
- Arachidonic (20:4)
- Adrenic (22:4)
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| ω-7 Unsaturated |
- Palmitoleic (16:1)
- Vaccenic (18:1)
- Paullinic (20:1)
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| ω−9 Unsaturated |
- Oleic (18:1)
- Elaidic (trans-18:1)
- Gondoic (20:1)
- Erucic (22:1)
- Nervonic (24:1)
- Mead (20:3)
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- Biochemical families
- carbohydrates
- alcohols
- glycoproteins
- glycosides
- lipids
- eicosanoids
- fatty acids / intermediates
- glycerides
- phospholipids
- sphingolipids
- steroids
- nucleic acids
- constituents / intermediates
- proteins
- amino acids / intermediates
- tetrapyrroles / intermediates
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