octanoic acid (CHEBI:28837)

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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A straight-chain saturated fatty acid that is heptane in which one of the hydrogens of a terminal methyl group has been replaced by a carboxy group.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

Supplier Information	ChemicalBook:CB7143511, eMolecules:32177433, eMolecules:491396, ZINC000169743172

Download	Molfile XML SDF

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Molfile

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The Resolver thinks Mol

Mrv0541 06161411353D

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Mrv0541 06161411353D

26 25 0 0 0 0 999 V2000

2.2541 3.0716 2.2144 C 0 0 0 0 0 0 0 0 0 0 0 0

0.9949 2.4437 1.8729 C 0 0 2 0 0 0 0 0 0 0 0 0

1.1749 1.2897 0.8560 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.1551 0.5978 0.4770 C 0 0 1 0 0 0 0 0 0 0 0 0

0.0447 -0.5593 -0.5305 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.2869 -1.2486 -0.9082 C 0 0 2 0 0 0 0 0 0 0 0 0

-1.1078 -2.4076 -1.9167 C 0 0 2 0 0 0 0 0 0 0 0 0

-2.4451 -3.0827 -2.2835 C 0 0 0 0 0 0 0 0 0 0 0 0

2.4657 4.2496 1.9704 O 0 0 0 0 0 0 0 0 0 0 0 0

3.1434 2.4177 2.7469 O 0 0 0 0 0 0 0 0 0 0 0 0

0.3017 3.1785 1.4521 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5370 2.0610 2.7890 H 0 0 0 0 0 0 0 0 0 0 0 0

1.8462 0.5345 1.2762 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6410 1.6804 -0.0538 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6246 0.2062 1.3840 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.8327 1.3389 0.0435 H 0 0 0 0 0 0 0 0 0 0 0 0

0.7210 -1.3015 -0.0963 H 0 0 0 0 0 0 0 0 0 0 0 0

0.5163 -0.1692 -1.4370 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.9608 -0.5019 -1.3378 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.7541 -1.6357 0.0020 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4382 -3.1608 -1.4924 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.6433 -2.0275 -2.8308 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.2730 -3.8913 -2.9950 H 0 0 0 0 0 0 0 0 0 0 0 0

-3.1258 -2.3603 -2.7383 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.9195 -3.4998 -1.3931 H 0 0 0 0 0 0 0 0 0 0 0 0

3.9258 2.7766 2.9292 H 0 0 0 0 0 0 0 0 0 0 0 0

2 1 1 0 0 0 0

10 1 1 0 0 0 0

9 1 2 0 0 0 0

3 2 1 0 0 0 0

4 3 1 0 0 0 0

5 4 1 0 0 0 0

6 5 1 0 0 0 0

7 6 1 0 0 0 0

8 7 1 0 0 0 0

2 11 1 0 0 0 0

2 12 1 0 0 0 0

3 13 1 0 0 0 0

3 14 1 0 0 0 0

4 15 1 0 0 0 0

4 16 1 0 0 0 0

5 17 1 0 0 0 0

5 18 1 0 0 0 0

6 19 1 0 0 0 0

6 20 1 0 0 0 0

7 21 1 0 0 0 0

7 22 1 0 0 0 0

8 23 1 0 0 0 0

8 24 1 0 0 0 0

8 25 1 0 0 0 0

10 26 1 0 0 0 0

M END): 50 ms

reading 26 atoms

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26 atoms created

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Wikipedia	License
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. Salts and esters of octanoic acid are known as octanoates or caprylates. The name of the related acyl group is octanoyl, capryloyl, or caprylyl. It is a common industrial chemical, which is produced by oxidation of the C8 aldehyde. Its compounds are found naturally in the milk of various mammals and as a minor constituent of coconut oil and palm kernel oil. 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.
Read full article at Wikipedia

Formula

C8H16O2

Net Charge

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	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.

CHEBI:28837 - octanoic acid

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