Sodium decanoate

Decanoic acid

Names
IUPAC name Decanoic acid
Other names Capric acid,n-Capric acid, n-Decanoic acid, Decylic acid, n-Decylic acid, C10:0 (Lipid numbers)
Identifiers
CAS Number	334-48-5 Y 1002-62-6 (sodium salt) N
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30813 Y
ChEMBL	ChEMBL107498 Y
ChemSpider	2863 Y
DrugBank	DB03600 N
ECHA InfoCard	100.005.798
EC Number	206-376-4
IUPHAR/BPS	5532
KEGG	C01571 Y
PubChem CID	2969
RTECS number	HD9100000
UNII	4G9EDB6V73 Y
InChI InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) Y Key: GHVNFZFCNZKVNT-UHFFFAOYSA-N Y InChI=1/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12) Key: GHVNFZFCNZKVNT-UHFFFAOYAC
SMILES O=C(O)CCCCCCCCC
Properties
Chemical formula	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)
Solubility in water	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)
Refractive index (nD)	1.4288 (40 °C)
Viscosity	4.327 cP (50 °C) 2.88 cP (70 °C)
Structure
Crystal structure	Monoclinic (−3.15 °C)
Space group	P21/c
Lattice constant	a = 23.1 Å, b = 4.973 Å, c = 9.716 Å α = 90°, β = 91.28°, γ = 90°
Thermochemistry
Specific heat capacity (C)	475.59 J/mol·K
Std enthalpy of formation (ΔfHo298)	−713.7 kJ/mol
Std enthalpy of combustion (ΔcHo298)	6079.3 kJ/mol
Hazards
Main hazards	Medium toxicity
Safety data sheet	External MSDS
GHS pictograms
GHS signal word	Warning
GHS hazard statements	H315, H319, H335
GHS precautionary statements	P261, P305+351+338
Ingestion hazard	May be toxic
Inhalation hazard	May cause irritation
Skin hazard	May be toxic on contact
NFPA 704	1 2 0
Flash point	110 °C (230 °F; 383 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)	10 g/kg (rats, oral)
Related compounds
Related fatty acids	Caprylic acid Lauric 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  (what is YN ?)
Infobox references

Decanoic acid (capric acid) is a saturated fatty acid (medium-chain triglyceride, MCT). 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.

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.