- For the term capric as it related to music see Capriccio (music)
Capric acid, n-Capric acid, n-Decanoic acid, Decylic acid, n-Decylic acid, C10:0 (Lipid numbers)
3D model (JSmol)
|Molar mass||172.27 g·mol−1|
|Odor||Strong rancid and unpleasant|
|Density||0.893 g/cm3 (25 °C)|
0.8884 g/cm3 (35.05 °C)
0.8773 g/cm3 (50.17 °C)
|Melting point||31.6 °C (88.9 °F; 304.8 K)|
|Boiling point||268.7 °C (515.7 °F; 541.8 K)|
|0.015 g/100 mL (20 °C)|
|Solubility||Soluble in alcohol, ether, CHCl3, C6H6, CS2, acetone|
|Vapor pressure||4.88·10−5 kPa (25 °C)|
0.1 kPa (108 °C)
2.03 kPa (160 °C)
|Thermal conductivity||0.372 W/m·K (solid)|
0.141 W/m·K (liquid)
Refractive index (nD)
|1.4288 (40 °C)|
|Viscosity||4.327 cP (50 °C)|
2.88 cP (70 °C)
|Monoclinic (−3.15 °C)|
α = 90°, β = 91.28°, γ = 90°
Heat capacity (C)
Std enthalpy of
Std enthalpy of
|Main hazards||Medium toxicity|
|Safety data sheet||External MSDS|
|GHS signal word||Warning|
|H315, H319, H335|
|Ingestion hazard||May be toxic|
|Inhalation hazard||May cause irritation|
|Skin hazard||May be toxic on contact|
|Flash point||110 °C (230 °F; 383 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|10 g/kg (rats, oral)|
Related fatty acids
|Nonanoic acid, Undecanoic acid|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Decanoic acid (capric acid, C10:0) is a saturated fatty acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called decanoates or "caprates". The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.
Capric acid occurs naturally in coconut oil (about 10%) and palm kernel oil (about 4%), otherwise it is uncommon in typical seed oils. It is found in the milk of various mammals and to a lesser extent in other animal fats. It also comprises 1.62% of the fats from the fruit of the durian species Durio graveolens.
Neutralization of decanoic acid or saponification of its esters, typically triglycerides, with sodium hydroxide will give sodium decanoate. This salt (CH3(CH2)8COO−Na+) is a component of some types of soap.
Decanoic acid is used in the manufacture of esters for artificial fruit flavors and perfumes. It is also used as an intermediate in chemical syntheses. It is used in organic synthesis and industrially in the manufacture of perfumes, lubricants, greases, rubber, dyes, plastics, food additives and pharmaceuticals.
Decanoate ester prodrugs of various pharmaceuticals are available. Since decanoic acid is a fatty acid, forming a salt or ester with a drug will increase its lipophilicity and its affinity for adipose tissue. Since distribution of a drug from fatty tissue is usually slow, one may develop a long-acting injectable form of a drug (called a Depot injection) by using its decanoate form. Some examples of drugs available as a decanoate ester include nandrolone, fluphenazine, bromperidol, and haloperidol.
Decanoic acid acts as a non-competitive AMPA receptor antagonist at therapeutically relevant concentrations, in a voltage- and subunit-dependent manner, and this is sufficient to explain its antiseizure effects. This direct inhibition of excitatory neurotransmission by decanoic acid in the brain contributes to the anticonvulsant effect of the MCT ketogenic diet. Decanoic acid and the AMPA receptor antagonist drug perampanel act at separate sites on the AMPA receptor, and so it is possible that they have a cooperative effect at the AMPA receptor, suggesting that perampanel and the ketogenic diet could be synergistic.
Decanoic acid may be responsible for the mitochondrial proliferation associated with the ketogenic diet, and that this may occur via PPARγ receptor agonism and its target genes involved in mitochondrial biogenesis. Complex I activity of the electron transport chain is substantially elevated by decanoic acid treatment.
It should however be noted that orally ingested medium chain fatty acids would be very rapidly degraded by first-pass metabolism by being taken up in the liver via the portal vein, and are quickly metabolized via coenzyme A intermediates through β-oxidation and the citric acid cycle to produce carbon dioxide, acetate and ketone bodies. Whether the ketones β-hydroxybutryate and acetone have direct antiseizure activity is unclear
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