CHEBI:28837 - octanoic acid

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ChEBI Name octanoic acid
ChEBI ID CHEBI:28837
Definition A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group. Octanoic acid is also known as caprylic acid.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44501, CHEBI:3373, CHEBI:25648
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Formula C8H16O2
Net Charge 0
Average Mass 144.21140
Monoisotopic Mass 144.11503
InChI InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
InChIKey WWZKQHOCKIZLMA-UHFFFAOYSA-N
SMILES CCCCCCCC(O)=O
Metabolite of Species Details
Escherichia coli (NCBI:txid562) See: PubMed
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): Escherichia coli metabolite
Any bacterial metabolite produced during a metabolic reaction in Escherichia coli.
antibacterial agent
A substance (or active part thereof) that kills or slows the growth of bacteria.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
View more via ChEBI Ontology
ChEBI Ontology
Outgoing octanoic acid (CHEBI:28837) has role Escherichia coli metabolite (CHEBI:76971)
octanoic acid (CHEBI:28837) has role antibacterial agent (CHEBI:33282)
octanoic acid (CHEBI:28837) has role human metabolite (CHEBI:77746)
octanoic acid (CHEBI:28837) is a medium-chain fatty acid (CHEBI:59554)
octanoic acid (CHEBI:28837) is a straight-chain saturated fatty acid (CHEBI:39418)
octanoic acid (CHEBI:28837) is conjugate acid of octanoate (CHEBI:25646)
Incoming (+)-pentacycloanammoxic acid (CHEBI:132927) has functional parent octanoic acid (CHEBI:28837)
(3S,4S)-3-hydroxy-4-methyloctanoic acid (CHEBI:72563) has functional parent octanoic acid (CHEBI:28837)
(7R)-7-hydroxyoctanoic acid (CHEBI:78949) has functional parent octanoic acid (CHEBI:28837)
(R)-lipoic acid (CHEBI:30314) has functional parent octanoic acid (CHEBI:28837)
(S)-lipoic acid (CHEBI:43796) has functional parent octanoic acid (CHEBI:28837)
1,2-dioctanoyl-3-β-D-galactosyl-sn-glycerol (CHEBI:90453) has functional parent octanoic acid (CHEBI:28837)
1,3-dioctanoylglycerol (CHEBI:136814) has functional parent octanoic acid (CHEBI:28837)
1-O-(α-D-galactopyranosyl)-N-octanoylphytosphingosine (CHEBI:527437) has functional parent octanoic acid (CHEBI:28837)
1-octadecanoyl-2-octanoyl-sn-glycero-3-phosphocholine (CHEBI:138213) has functional parent octanoic acid (CHEBI:28837)
2-(pentylsulfanyl)acetic acid (CHEBI:65241) has functional parent octanoic acid (CHEBI:28837)
2-O-[6-O-octanoyl-α-D-glucosyl-(1→6)-α-D-glucosyl]-D-glyceric acid (CHEBI:137553) has functional parent octanoic acid (CHEBI:28837)
2-hydroxyoctanoic acid (CHEBI:86543) has functional parent octanoic acid (CHEBI:28837)
2-octanoyl-sn-glycero-3-phosphocholine (CHEBI:140082) has functional parent octanoic acid (CHEBI:28837)
2-oxooctanoic acid (CHEBI:173668) has functional parent octanoic acid (CHEBI:28837)
3-aminooctanoic acid (CHEBI:73739) has functional parent octanoic acid (CHEBI:28837)
3-hydroxyoctanoic acid (CHEBI:37098) has functional parent octanoic acid (CHEBI:28837)
3-methylbutyl octanoate (CHEBI:87536) has functional parent octanoic acid (CHEBI:28837)
3-oxooctanoic acid (CHEBI:44680) has functional parent octanoic acid (CHEBI:28837)
4,7-dioxooctanoic acid (CHEBI:73742) has functional parent octanoic acid (CHEBI:28837)
6-hydroxy-3,7-dimethyloctanoic acid (CHEBI:50451) has functional parent octanoic acid (CHEBI:28837)
8-(5-hexylfuran-2-yl)octanoic acid (CHEBI:34491) has functional parent octanoic acid (CHEBI:28837)
8-hydroxyoctanoic acid (CHEBI:79162) has functional parent octanoic acid (CHEBI:28837)
8-{3-oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}octanoic acid (CHEBI:191853) has functional parent octanoic acid (CHEBI:28837)
N-(octanoyl)-L-homoserine (CHEBI:74404) has functional parent octanoic acid (CHEBI:28837)
N-(octanoyl)ethanolamine (CHEBI:85302) has functional parent octanoic acid (CHEBI:28837)
N-capryloyl-1-palmitoyl-2-linoleoyl-sn-glycero-3-phosphoethanolamine (CHEBI:85797) has functional parent octanoic acid (CHEBI:28837)
N-octanoyl-(2S)-hydroxyglycine (CHEBI:142745) has functional parent octanoic acid (CHEBI:28837)
N-octanoylanthranilate (CHEBI:143722) has functional parent octanoic acid (CHEBI:28837)
N-octanoylanthranilic acid (CHEBI:143902) has functional parent octanoic acid (CHEBI:28837)
N-octanoyldihydrosphingosine (CHEBI:82841) has functional parent octanoic acid (CHEBI:28837)
N-octanoylglycine (CHEBI:74099) has functional parent octanoic acid (CHEBI:28837)
N-octanoylphytosphingosine (CHEBI:82842) has functional parent octanoic acid (CHEBI:28837)
N-octanoylsphingosine (CHEBI:45815) has functional parent octanoic acid (CHEBI:28837)
N-octanoylsphingosine 1-phosphate (CHEBI:85881) has functional parent octanoic acid (CHEBI:28837)
S-octanoyl-4ʼ-phosphopantetheine (CHEBI:132312) has functional parent octanoic acid (CHEBI:28837)
S-octanoyl-L-cysteine (CHEBI:134410) has functional parent octanoic acid (CHEBI:28837)
ciliatamide B (CHEBI:65631) has functional parent octanoic acid (CHEBI:28837)
dihydrolipoic acid (CHEBI:18047) has functional parent octanoic acid (CHEBI:28837)
lipoic acid (CHEBI:16494) has functional parent octanoic acid (CHEBI:28837)
lipoyl group (CHEBI:25064) has functional parent octanoic acid (CHEBI:28837)
lipoyl-AMP (CHEBI:55451) has functional parent octanoic acid (CHEBI:28837)
methyl (+)-pentacycloanammoxate (CHEBI:132928) has functional parent octanoic acid (CHEBI:28837)
octanamide (CHEBI:142682) has functional parent octanoic acid (CHEBI:28837)
octanoate ester (CHEBI:87657) has functional parent octanoic acid (CHEBI:28837)
octanoyl-CoA (CHEBI:15533) has functional parent octanoic acid (CHEBI:28837)
octanoyloxidanyl (CHEBI:192808) has functional parent octanoic acid (CHEBI:28837)
perfluorooctanoic acid (CHEBI:35549) has functional parent octanoic acid (CHEBI:28837)
pescaprein XXX (CHEBI:67860) has functional parent octanoic acid (CHEBI:28837)
octanoate (CHEBI:25646) is conjugate base of octanoic acid (CHEBI:28837)
octanoyl group (CHEBI:25650) is substituent group from octanoic acid (CHEBI:28837)
IUPAC Name
octanoic acid
INNs Sources
acide octanoïque WHO MedNet
ácido octanoico WHO MedNet
acidum octanoicum WHO MedNet
octanoic acid WHO MedNet
Synonyms Sources
1-heptanecarboxylic acid ChemIDplus
8:0 ChEBI
Acide octanoique ChemIDplus
Acido octanoico ChemIDplus
Acidum octanocium ChemIDplus
C8:0 ChEBI
Caprylic acid KEGG COMPOUND
Caprylic acid KEGG COMPOUND
CH3‒[CH2]6‒COOH IUPAC
Kaprylsäure ChEBI
n-caprylic acid ChemIDplus
n-octanoic acid NIST Chemistry WebBook
n-octoic acid ChemIDplus
n-octylic acid ChemIDplus
Octanoic acid KEGG COMPOUND
OCTANOIC ACID (CAPRYLIC ACID) PDBeChem
Octansäure ChEBI
octoic acid NIST Chemistry WebBook
Octylic acid KEGG COMPOUND
Manual Xrefs Databases
3998 DrugCentral
C00001231 KNApSAcK
C06423 KEGG COMPOUND
Caprylic_acid Wikipedia
CPD-195 MetaCyc
D05220 KEGG DRUG
DB04519 DrugBank
HMDB0000482 HMDB
LMFA01010008 LIPID MAPS
OCA PDBeChem
View more database links
Registry Numbers Types Sources
124-07-2 CAS Registry Number KEGG COMPOUND
124-07-2 CAS Registry Number ChemIDplus
124-07-2 CAS Registry Number NIST Chemistry WebBook
142966 Gmelin Registry Number Gmelin
1747180 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16162522 PubMed citation Europe PMC
16872526 PubMed citation Europe PMC
19096058 PubMed citation Europe PMC
Last Modified
13 May 2022
General Comment
2011-03-29 Caprylic acid, together with caproic (C6) and capric (C10) acids, constitutes 15% of goat milk fat (L. caper = goat). Also found naturally in coconuts and breast milk, it makes up 70% of the fatty acids in commercial medium chain triglycerides (MCT) and is used commercially to produce esters used in perfumery; in dye manufacture; and therapeutically as an antimicrobial agent in the livestock industry.