hexanoic acid (CHEBI:30776)

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CHEBI:30776 - hexanoic acid

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ChEBI Name	hexanoic acid

ChEBI ID	CHEBI:30776

Definition	A C₆, straight-chain saturated fatty acid.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:40213, CHEBI:24571, CHEBI:5702

Supplier Information	ChemicalBook:CB3224164, eMolecules:483343, ZINC000001529230

Download	Molfile XML SDF

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20 19 0 0 0 0 999 V2000

2.2870 1.7631 -1.2050 C 0 0 0 0 0 0 0 0 0 0 0 0

0.8968 1.5237 -0.8791 C 0 0 0 0 0 0 0 0 0 0 0 0

0.6812 0.1813 -0.1318 C 0 0 0 0 0 0 0 0 0 0 0 0

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-1.0157 -1.4452 0.9612 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.4960 -1.7093 1.3085 C 0 0 0 0 0 0 0 0 0 0 0 0

2.8927 2.7265 -0.7572 O 0 0 0 0 0 0 0 0 0 0 0 0

2.8923 0.9876 -1.9363 O 0 0 0 0 0 0 0 0 0 0 0 0

0.3201 1.5264 -1.8083 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5046 2.3377 -0.2612 H 0 0 0 0 0 0 0 0 0 0 0 0

1.2710 0.1873 0.7899 H 0 0 0 0 0 0 0 0 0 0 0 0

1.0475 -0.6414 -0.7536 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.3872 -0.1033 -0.6984 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.1712 0.7136 0.8526 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6528 -2.2674 0.3381 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4339 -1.4531 1.8872 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.5982 -2.6643 1.8262 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1023 -1.7434 0.4010 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.8833 -0.9222 1.9588 H 0 0 0 0 0 0 0 0 0 0 0 0

3.7462 1.1023 -2.1161 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 1 0 0 0 0

8 1 1 0 0 0 0

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2 9 1 0 0 0 0

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4 14 1 0 0 0 0

5 15 1 0 0 0 0

5 16 1 0 0 0 0

6 17 1 0 0 0 0

6 18 1 0 0 0 0

6 19 1 0 0 0 0

8 20 1 0 0 0 0

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Wikipedia	License
Caproic acid, also known as hexanoic acid, is the carboxylic acid derived from hexane with the chemical formula CH3(CH2)4COOH. It is a colorless oily liquid with a fatty, cheesy, waxy odor resembling that of goats or other barnyard animals. It is a fatty acid found naturally in various animal fats and oils, and is one of the chemicals that gives the decomposing fleshy seed coat of the ginkgo its characteristic unpleasant odor. It is also one of the components of vanilla and cheese. The primary use of caproic acid is in the manufacture of its esters for use as artificial flavors, and in the manufacture of hexyl derivatives, such as hexylphenols. Salts and esters of caproic acid are known as caproates or hexanoates. Several progestin medications are caproate esters, such as hydroxyprogesterone caproate and gestonorone caproate. Two other acids are named after goats: caprylic acid (C8) and capric acid (C10). Along with caproic acid, they account for 15% of the fat in goat's milk. Caproic, caprylic, and capric acids (capric is a crystal- or wax-like substance, whereas the other two are mobile liquids) are not only used for the formation of esters, but also commonly used "neat" in: butter, milk, cream, strawberry, bread, beer, nut, and other flavors.
Read full article at Wikipedia

Formula

C6H12O2

Net Charge

Average Mass

116.15830

Monoisotopic Mass

116.08373

InChI

InChI=1S/C6H12O2/c1-2-3-4-5-6(7)8/h2-5H2,1H3,(H,7,8)

InChIKey

FUZZWVXGSFPDMH-UHFFFAOYSA-N

SMILES

CCCCCC(O)=O

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	plant metabolite Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	hexanoic acid (CHEBI:30776) has role human metabolite (CHEBI:77746) hexanoic acid (CHEBI:30776) has role plant metabolite (CHEBI:76924) hexanoic acid (CHEBI:30776) is a medium-chain fatty acid (CHEBI:59554) hexanoic acid (CHEBI:30776) is a straight-chain saturated fatty acid (CHEBI:39418) hexanoic acid (CHEBI:30776) is conjugate acid of hexanoate (CHEBI:17120)

Incoming	(3R)-3,6-diaminohexanoic acid (CHEBI:85040) has functional parent hexanoic acid (CHEBI:30776) (3S)-3,6-diaminohexanoic acid (CHEBI:15613) has functional parent hexanoic acid (CHEBI:30776) (3S,5S)-3,5-diaminohexanoic acid (CHEBI:15616) has functional parent hexanoic acid (CHEBI:30776) (4S,5S)-4,5-dihydroxy-2,6-dioxohexanoic acid (CHEBI:15624) has functional parent hexanoic acid (CHEBI:30776) (5R)-5-hydroxyhexanoic acid (CHEBI:78842) has functional parent hexanoic acid (CHEBI:30776) (5S)-5-amino-3-oxohexanoic acid (CHEBI:27713) has functional parent hexanoic acid (CHEBI:30776) (9R,13R)-1a,1b-dinor-10,11-dihydro-12-oxo-15-phytoenoic acid (CHEBI:139085) has functional parent hexanoic acid (CHEBI:30776) (R)-3-hydroxyhexanoyl-CoA (CHEBI:74474) has functional parent hexanoic acid (CHEBI:30776) (S)-(+)-4-(5-carboxypentyl)methamphetamine (CHEBI:67238) has functional parent hexanoic acid (CHEBI:30776) 1,2-dihexanoyl-sn-glycero-3-phosphocholine (CHEBI:138194) has functional parent hexanoic acid (CHEBI:30776) 1,2-dihexanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:138922) has functional parent hexanoic acid (CHEBI:30776) 1,2-dihexanoyl-sn-glycerol (CHEBI:140526) has functional parent hexanoic acid (CHEBI:30776) 1-heptanoyl-2-hexanoyl-sn-glycero-3-phosphocholine (CHEBI:138198) has functional parent hexanoic acid (CHEBI:30776) 1-heptanoyl-2-hexanoyl-sn-glycero-3-phosphoethanolamine (CHEBI:138923) has functional parent hexanoic acid (CHEBI:30776) 1-hexanoyl-2-heptanoyl-sn-glycero-3-phosphocholine (CHEBI:138197) has functional parent hexanoic acid (CHEBI:30776) 1-hexanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine (CHEBI:86282) has functional parent hexanoic acid (CHEBI:30776) 1-octadecanoyl-2-hexanoyl-sn-glycero-3-phosphocholine (CHEBI:138212) has functional parent hexanoic acid (CHEBI:30776) 2,5-diaminohexanoic acid (CHEBI:16926) has functional parent hexanoic acid (CHEBI:30776) 2,6-dioxo-6-phenylhexanoic acid (CHEBI:15707) has functional parent hexanoic acid (CHEBI:30776) 2-amino-5-oxohexanoic acid (CHEBI:19450) has functional parent hexanoic acid (CHEBI:30776) 2-aminohexanoic acid (CHEBI:36405) has functional parent hexanoic acid (CHEBI:30776) 2-hydroxyhexanoic acid (CHEBI:86542) has functional parent hexanoic acid (CHEBI:30776) 2-oxohexanoic acid (CHEBI:17308) has functional parent hexanoic acid (CHEBI:30776) 3-deoxy-D-glycero-hexo-2,5-diulosonic acid (CHEBI:15623) has functional parent hexanoic acid (CHEBI:30776) 3-hydroxy-5-oxohexanoic acid (CHEBI:37032) has functional parent hexanoic acid (CHEBI:30776) 3-oxohexanoic acid (CHEBI:28422) has functional parent hexanoic acid (CHEBI:30776) 4-hydroxy-2-oxohexanoic acid (CHEBI:27530) has functional parent hexanoic acid (CHEBI:30776) 5-hydroxyhexanoic acid (CHEBI:131434) has functional parent hexanoic acid (CHEBI:30776) 5-oxohexanoic acid (CHEBI:15888) has functional parent hexanoic acid (CHEBI:30776) 6-acetamido-3-aminohexanoic acid (CHEBI:2164) has functional parent hexanoic acid (CHEBI:30776) 6-amino-2-oxohexanoic acid (CHEBI:17534) has functional parent hexanoic acid (CHEBI:30776) 6-aminohexanoic acid (CHEBI:16586) has functional parent hexanoic acid (CHEBI:30776) 6-bromohexanoic acid (CHEBI:60700) has functional parent hexanoic acid (CHEBI:30776) 6-hydroxy-2-oxohexanoic acid (CHEBI:28028) has functional parent hexanoic acid (CHEBI:30776) 6-hydroxyhexanoic acid (CHEBI:17869) has functional parent hexanoic acid (CHEBI:30776) 6-oxohexanoic acid (CHEBI:2490) has functional parent hexanoic acid (CHEBI:30776) 6-{4-[hydroxy-(4-nitrophenoxy)phosphoryl]butyrylamino}hexanoic acid (CHEBI:45068) has functional parent hexanoic acid (CHEBI:30776) N-(6-aminohexanoyl)-6-aminohexanoic acid (CHEBI:49255) has functional parent hexanoic acid (CHEBI:30776) N-(hexanoyl)ethanolamine (CHEBI:85303) has functional parent hexanoic acid (CHEBI:30776) N-caproyl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85798) has functional parent hexanoic acid (CHEBI:30776) N-hexanoyl-β-D-galactosylsphinganine (CHEBI:83251) has functional parent hexanoic acid (CHEBI:30776) N-hexanoyl-(2S)-hydroxyglycine (CHEBI:142746) has functional parent hexanoic acid (CHEBI:30776) N-hexanoyldihydroceramide (CHEBI:76226) has functional parent hexanoic acid (CHEBI:30776) N-hexanoylphytosphingosine (CHEBI:88095) has functional parent hexanoic acid (CHEBI:30776) N-hexanoylphytosphingosine 1-phosphate (CHEBI:90165) has functional parent hexanoic acid (CHEBI:30776) N-hexanoylsphingosine 1-phosphate (CHEBI:83798) has functional parent hexanoic acid (CHEBI:30776) N-hexanoylsphingosine-1-phosphocholine (CHEBI:78254) has functional parent hexanoic acid (CHEBI:30776) N-hexanoylsphingosine-1-phosphoethanolamine (CHEBI:79069) has functional parent hexanoic acid (CHEBI:30776) S-hexanoyl-4ʼ-phosphopantetheine (CHEBI:132311) has functional parent hexanoic acid (CHEBI:30776) S-propyl hexanethioate (CHEBI:180249) has functional parent hexanoic acid (CHEBI:30776) caproylcholine (CHEBI:74096) has functional parent hexanoic acid (CHEBI:30776) dethiobiotin (CHEBI:16691) has functional parent hexanoic acid (CHEBI:30776) hexanamide (CHEBI:142683) has functional parent hexanoic acid (CHEBI:30776) hexanoate ester (CHEBI:87656) has functional parent hexanoic acid (CHEBI:30776) hexanoyl-CoA (CHEBI:27540) has functional parent hexanoic acid (CHEBI:30776) lysine (CHEBI:25094) has functional parent hexanoic acid (CHEBI:30776) lysophosphatidylcholine 6:0 (CHEBI:85563) has functional parent hexanoic acid (CHEBI:30776) perfluorohexanoic acid (CHEBI:83492) has functional parent hexanoic acid (CHEBI:30776) pescaprein XXIX (CHEBI:67859) has functional parent hexanoic acid (CHEBI:30776) hexanoate (CHEBI:17120) is conjugate base of hexanoic acid (CHEBI:30776) hexanoyl group (CHEBI:24574) is substituent group from hexanoic acid (CHEBI:30776)

IUPAC Name

hexanoic acid

Synonyms	Sources
1-hexanoic acid	ChemIDplus
1-pentanecarboxylic acid	ChemIDplus
6:0	ChEBI
butylacetic acid	ChemIDplus
C6:0	ChEBI
caproic acid	ChEBI
capronic acid	NIST Chemistry WebBook
CH₃‒[CH₂]₄‒COOH	IUPAC
Hexanoate	KEGG COMPOUND
Hexanoic acid	KEGG COMPOUND
HEXANOIC ACID	PDBeChem
hexoic acid	NIST Chemistry WebBook
Hexylic acid	KEGG COMPOUND
n-Caproic acid	KEGG COMPOUND
n-hexanoic acid	NIST Chemistry WebBook
n-hexoic acid	ChemIDplus
n-hexylic acid	ChemIDplus
Pentanecarboxylic acid	ChemIDplus
pentiformic acid	ChemIDplus
pentylformic acid	ChemIDplus

Manual Xrefs	Databases
6NA	PDBeChem
C00001218	KNApSAcK
C01585	KEGG COMPOUND
ECMDB21229	ECMDB
HEXANOATE	MetaCyc
Hexanoic_acid	Wikipedia
HMDB0000535	HMDB
LMFA01010006	LIPID MAPS
YMDB01424	YMDB
View more database links

Registry Numbers	Types	Sources
142-62-1	CAS Registry Number	KEGG COMPOUND
142-62-1	CAS Registry Number	ChemIDplus
142-62-1	CAS Registry Number	NIST Chemistry WebBook
185066	Gmelin Registry Number	Gmelin
773837	Reaxys Registry Number	Reaxys

Citations

Running CA, Mattes RD (2014)
Different oral sensitivities to and sensations of short-, medium-, and long-chain fatty acids in humans.
American journal of physiology. Gastrointestinal and liver physiology 307, G381-9 [PubMed:24924750]
[show Abstract]

Öztürk M, Geçgel U, Duran A, Uslu N, Özcan MM (2014)
The fatty acid compositions of several plant seed oils belong to Leguminosae and Umbelliferae families.
Environmental monitoring and assessment 186, 2795-2799 [PubMed:24357269]
[show Abstract]

Traul KA, Driedger A, Ingle DL, Nakhasi D (2000)
Review of the toxicologic properties of medium-chain triglycerides.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association 38, 79-98 [PubMed:10685018]
[show Abstract]
Medium chain triglycerides (MCTs) are a family of triglycerides, containing predominantly, caprylic (C(8)) and capric (C(10)) fatty acids with lesser amounts of caproic (C(6)) and lauric (C(12)) fatty acids. MCTs are widely used for parenteral nutrition in individuals requiring supplemental nutrition and are being more widely used in foods, drugs and cosmetics. MCTs are essentially non-toxic in acute toxicity tests conducted in several species of animals. In ocular and dermal irritation testing MCTs exhibit virtually no potential as ocular or dermal irritants, even with prolonged eye or skin exposure. MCTs exhibit no capacity for induction of hypersensitivity. Ninety-day toxicity tests did not result in notable toxicity, whether the product was administered in the diet up to 9375mg/kg body weight/day or by intramuscular (im) injection (up to 0. 5ml/kg/day, rabbits). There was no evidence that intravenous (iv) or dietary administration of MCTs adversely affected the reproductive performance of rats or resulted in maternal toxicity, foetal toxicity or teratogenic effects at doses up to 4.28g/kg body weight/day (iv) or 12,500mg/kg body weight/day (dietary). There was no evidence that dietary administration of MCTs adversely affected the reproductive performance of pigs or resulted in maternal toxicity, foetal toxicity or teratogenic effects at doses up to 4000mg/kg body weight/day in the diet. In rabbits, following iv administration, the maternal and foetal no-observed-adverse-effect levels (NOAELs) were between 1.0 and 4.28g/kg body weight/ day. A 2-year study in rats, conducted with a closely related compound (tricaprylin, a triglyceride with C(8) fatty acids), provided no evidence of a carcinogenic effect when the material was administered by oral gavage at levels up to 10ml/kg (9.54g/kg) per day. Although tricaprylin was found to be positive in one of five strains of Salmonella typhimurium in the presence of metabolic activation in an Ames mutagenicity assay, the results of the carcinogenicity test with tricaprylin and mutagenicity tests with caprylic acid indicate that MCTs do not have the potential to be carcinogenic or mutagenic. The safety of human dietary consumption of MCTs, up to levels of 1g/kg, has been confirmed in several clinical trials.

Miyata S, Monnier V (1992)
Immunohistochemical detection of advanced glycosylation end products in diabetic tissues using monoclonal antibody to pyrraline.
The Journal of clinical investigation 89, 1102-1112 [PubMed:1556177]
[show Abstract]

Last Modified

11 May 2023

General Comment
2011-03-29	Together with caprylic (C₈) and capric (C₁₀) acids, caproic acid constitutes 15% of goat milk fat (L. caper = goat).

CHEBI:30776 - hexanoic acid

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