Decanoate
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| Names | |
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IUPAC name
Decanoic acid
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| Other names
Capric acid,n-Capric acid, n-Decanoic acid, Decylic acid, n-Decylic acid, C10:0 (Lipid numbers)
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| Identifiers | |
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3D model (Jmol)
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| ChEBI | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.005.798 |
| EC Number | 206-376-4 |
| KEGG | |
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PubChem CID
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| RTECS number | HD9100000 |
| UNII | |
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| Properties | |
| C10H20O2 | |
| Molar mass | 172.27 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) |
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Refractive index (nD)
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1.4288 (40 °C) |
| Viscosity | 4.327 cP (50 °C) 2.88 cP (70 °C) |
| Structure | |
| Monoclinic (−3.15 °C) | |
| P21/c | |
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a = 23.1 Å, b = 4.973 Å, c = 9.716 Å
α = 90°, β = 91.28°, γ = 90°
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| Thermochemistry | |
| 475.59 J/mol·K | |
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Std enthalpy of
formation (ΔfH |
−713.7 kJ/mol |
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Std enthalpy of
combustion (ΔcH |
6079.3 kJ/mol |
| Hazards | |
| Main hazards | Medium toxicity |
| Safety data sheet | External MSDS |
| GHS pictograms |  |
| GHS signal word | Warning |
| H315, H319, H335 | |
| P261, P305+351+338 | |
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EU classification (DSD)
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 Xi |
| R-phrases | R36/37/38 |
| S-phrases | S24/25, S26, S36/37/39 |
| Ingestion hazard | May be toxic |
| Inhalation hazard | May cause irritation |
| Skin hazard | May be toxic on contact |
| NFPA 704 | |
| Flash point | 110 °C (230 °F; 383 K) |
| Lethal dose or concentration (LD, LC): | |
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LD50 (median dose)
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10 g/kg (rats, oral) |
| Related compounds | |
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Related fatty acids
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Caprylic acid Lauric acid |
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Related compounds
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Decanol Decanal |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
Decanoic acid (capric acid) 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.
Two other acids are named after goats: caproic (a C6 fatty acid) and caprylic (a C8 fatty acid). Along with decanoic acid, these total 15% in goat milk fat.
Decanoic acid can be prepared from oxidation of primary alcohol decanol by using chromium trioxide (CrO3) oxidant under acidic conditions.
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 fatty 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.
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