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Fatty acids
Capric acid
Другие языки:

Capric acid

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Not to be confused with Caproic acid or Caprylic acid.
Decanoic acid
Skeletal formula of decanoic acid
Ball-and-stick model of decanoic acid
Names
Preferred IUPAC name
Decanoic acid
Other names
Caprinic acid; Caprynic acid; Decoic acid; Decylic acid;
1-Nonanecarboxylic acid;
C10:0 (Lipid numbers)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.005.798
EC Number
  • 206-376-4
KEGG
PubChem CID
RTECS number
  • HD9100000
UNII
  • InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) checkY
    Key: GHVNFZFCNZKVNT-UHFFFAOYSA-N checkY
  • InChI=1/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)
    Key: GHVNFZFCNZKVNT-UHFFFAOYAC
  • O=C(O)CCCCCCCCC
Properties
C10H20O2
Molar mass 172.268 g·mol−1
Appearance White crystals
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
log P 4.09
Vapor pressure 4.88·10−5 kPa (25 °C)
0.1 kPa (108 °C)
2.03 kPa (160 °C)
Acidity (pKa) 4.9
Thermal conductivity 0.372 W/m·K (solid)
0.141 W/m·K (liquid)
1.4288 (40 °C)
Viscosity 4.327 cP (50 °C)
2.88 cP (70 °C)
Structure
Monoclinic (−3.15 °C)
P21/c
a = 23.1 Å, b = 4.973 Å, c = 9.716 Å
α = 90°, β = 91.28°, γ = 90°
Thermochemistry
475.59 J/mol·K
−713.7 kJ/mol
6079.3 kJ/mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Medium toxicity
Ingestion hazards
 May be toxic
Inhalation hazards
 May cause irritation
Skin hazards
 May be toxic on contact
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P305+P351+P338
NFPA 704 (fire diamond)
2
1
0
Flash point 110 °C (230 °F; 383 K)
Lethal dose or concentration (LD, LC):
10 g/kg (rats, oral)
Safety data sheet (SDS) External MSDS
Related compounds
Related fatty acids
Nonanoic acid, Undecanoic acid
Related compounds
 Decanol
Decanal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Capric acid, also known as decanoic acid or decylic acid, is a saturated fatty acid, medium-chain fatty acid (MCFA), and carboxylic acid. Its formula is CH3(CH2)8COOH. Salts and esters of decanoic acid are called caprates or decanoates. The term capric acid is derived from the Latin "caper / capra" (goat) because the sweaty, unpleasant smell of the compound is reminiscent of goats.

Occurrence

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.

Two other acids are named after goats: caproic acid (a C6:0 fatty acid) and caprylic acid (a C8:0 fatty acid). Along with capric acid, these total 15% in goat milk fat.

Production

Capric acid can be prepared from oxidation of the primary alcohol decanol by using chromium trioxide (CrO3) oxidant under acidic conditions.

Neutralization of capric acid or saponification of its triglyceride esters with sodium hydroxide yields sodium caprate, CH3(CH2)8CO−2Na+. This salt is a component of some types of soap.

Uses

Capric 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.

Pharmaceuticals

Caprate ester prodrugs of various pharmaceuticals are available. Since capric 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 caprate form. Some examples of drugs available as a caprate ester include nandrolone, fluphenazine, bromperidol, and haloperidol.

Effects

Capric 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 capric 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.

Capric 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.

See also


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