Caprylic acid

Caprylic acid
Names
	Preferred IUPAC name Octanoic acid
	Other names 1-Heptanecarboxylic acid; Octylic acid; Octoic acid; C8:0 (lipid numbers)
Identifiers
CAS Number	124-07-2 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28837 ;
ChEMBL	ChEMBL324846 ;
ChemSpider	370 ;
DrugBank	DB04519 ;
ECHA InfoCard	100.004.253
EC Number	204-677-5;
IUPHAR/BPS	4585;
KEGG	D05220 ;
PubChem CID	379;
UNII	OBL58JN025 ;
CompTox Dashboard (EPA)	DTXSID3021645 ;
	InChI InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) Key: WWZKQHOCKIZLMA-UHFFFAOYSA-N ; InChI=1/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10) Key: WWZKQHOCKIZLMA-UHFFFAOYAH;
	SMILES CCCCCCCC(=O)O;
Properties
Chemical formula	C8H16O2
Molar mass	144.214 g/mol
Appearance	Oily colorless liquid
Odor	Faint, fruity-acid; irritating
Density	0.910 g/cm3
Melting point	16.7 °C (62.1 °F; 289.8 K)
Boiling point	239.7 °C (463.5 °F; 512.8 K)
Solubility in water	0.068 g/100 mL
Solubility	Soluble in alcohol, chloroform, ether, CS2, petroleum ether, acetonitrile
log P	3.05
Vapor pressure	0.25 Pa
Acidity (pKa)	4.89; 1.055 (2.06–2.63 K); 1.53 (−191 °C);
Magnetic susceptibility (χ)	−101.60·10−6 cm3/mol
Refractive index (nD)	1.4285
Thermochemistry
Heat capacity (C)	297.9 J/K·mol
Std enthalpy of; formation (ΔfH⦵298)	−636 kJ/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314
Precautionary statements	P264, P280, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310, P363, P405, P501
NFPA 704 (fire diamond)	3 0 1 COR
Flash point	130 °C (266 °F; 403 K)
Autoignition; temperature	440 °C (824 °F; 713 K)
	Lethal dose or concentration (LD, LC):
LD50 (median dose)	10.08 g/kg (orally in rats)
Related compounds
Related compounds	Heptanoic acid, nonanoic acid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Caprylic acid (from Latin capra 'goat'), also known under the systematic name octanoic acid or C8 Acid, is a saturated fatty acid, medium-chain fatty acid (MCFA). It has the structural formula H₃C−(CH₂)₆−COOH, and is a colorless oily liquid that is minimally soluble in water with a slightly unpleasant rancid-like smell and taste.^[1] Salts and esters of octanoic acid are known as octanoates or caprylates. The name of the related acyl group is octanoyl, capryloyl, or caprylyl.^[5] It is a common industrial chemical, which is produced by oxidation of the C8 aldehyde.^[6] Its compounds are found naturally in the milk of various mammals and as a minor constituent of coconut oil and palm kernel oil.^[3]

Two other acids are named after goats via the Latin word capra: caproic acid (C6) and capric acid (C10). Together, these three fatty acids comprise 15% of the fatty acids in goat milk fat.

^ ^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.
^ ^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. S2CID 84492006.
^ Sigma-Aldrich Co., Octanoic acid. Retrieved on 2022-08-11.
^ "CHEBI:25650 - octanoyl group". Chemical Entities of Biological Interest (ChEBI). 23 November 2010. Retrieved 4 July 2024.
^ Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235. ISBN 978-3527306732.

[Merck-1] Budavari, Susan, ed. (1996), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (12th ed.), Merck, ISBN 0911910123

[crc-2] Lide, D.R. (Ed.) (1990). CRC Handbook of Chemistry and Physics (70th Edn.). Boca Raton (FL):CRC Press.

[lexicon-3] 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. S2CID 84492006.

[sigma-4] Sigma-Aldrich Co., Octanoic acid. Retrieved on 2022-08-11.

[5] "CHEBI:25650 - octanoyl group". Chemical Entities of Biological Interest (ChEBI). 23 November 2010. Retrieved 4 July 2024.

[Ullmann-6] Riemenschneider, Wilhelm (2002). "Carboxylic Acids, Aliphatic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a05_235. ISBN 978-3527306732.

[1]

[3]

[2]

[4]

[5]

[6]

Names


Preferred IUPAC name Octanoic acid
Other names 1-Heptanecarboxylic acid Octylic acid Octoic acid C8:0 (lipid numbers)
Identifiers
CAS Number	124-07-2^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28837^Y
ChEMBL	ChEMBL324846^Y
ChemSpider	370^Y
DrugBank	DB04519^Y
ECHA InfoCard	100.004.253
EC Number	204-677-5
IUPHAR/BPS	4585
KEGG	D05220^Y
PubChem CID	379
UNII	OBL58JN025^Y
CompTox Dashboard (EPA)	DTXSID3021645
InChI 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
SMILES CCCCCCCC(=O)O
Properties
Chemical formula	C₈H₁₆O₂
Molar mass	144.214 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)^[3]
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 (pK_a)	4.89^[2] 1.055 (2.06–2.63 K) 1.53 (−191 °C)
Magnetic susceptibility (χ)	−101.60·10⁻⁶ cm³/mol
Refractive index (n_D)	1.4285
Thermochemistry
Heat capacity (C)	297.9 J/K·mol
Std enthalpy of formation (Δ_fH^⦵₂₉₈)	−636 kJ/mol
Hazards
GHS labelling:
Pictograms	^[4]
Signal word	Danger
Hazard statements	H314
Precautionary statements	P264, P280, P301+P330+P331, P303+P361+P353, P304+P340+P310, P305+P351+P338+P310, P363, P405, P501
NFPA 704 (fire diamond)	3 0 1 COR
Flash point	130 °C (266 °F; 403 K)
Autoignition temperature	440 °C (824 °F; 713 K)
Lethal dose or concentration (LD, LC):
LD₅₀ (median dose)	10.08 g/kg (orally in rats)^[1]
Related compounds
Related compounds	Heptanoic acid, nonanoic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references