| Caprylic acid |
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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 |
| KEGG |
D05220 Y |
| ChEBI |
CHEBI:28837 Y |
| ChEMBL |
CHEMBL324846 Y |
| Jmol-3D images |
Image 1 |
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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
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 |
| Molecular formula |
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] |
| Solubility in water |
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) |
1.4285 |
| Thermochemistry |
Specific
heat capacity C |
297.9 J/K mol |
Std enthalpy of
formation ΔfHo298 |
-636 kJ/mol |
| Hazards |
| NFPA 704 |
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| Flash point |
130 °C (266 °F; 403 K) |
| Autoignition temperature |
440 °C (824 °F; 713 K) |
| LD50 |
10.08 g/kg (orally in rats)[1] |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) |
| 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.
Medical uses
See also: Medium-chain triglyceride § Medical uses
Caprylic acid has medical uses as a medium-chain triglyceride.
Caprylic acid is also used in the treatment of some bacterial 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 Staphylococcus aureus and various species of Streptococcus.[7] The octanoic acid breath test is used to measure gastric emptying. Some potential benefit is possible from administration of octanoic acid for patients with Essential tremor.
Caprylic acid is taken as a dietary supplement within alternative medicine. It is believed to suppress fungal infections within the gut, notably candida albicans infection.
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.
- ^ Nair MK, Joy J, Vasudevan P, Hinckley L, Hoagland TA, Venkitanarayanan KS (Oct 2005). "Antibacterial effect of caprylic acid and monocaprylin on major bacterial mastitis pathogens". J Dairy Sci 88 (10): 3488–95. doi:10.3168/jds.S0022-0302(05)73033-2. PMID 16162522.
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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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