Record Information
Version1.0
Creation Date2016-09-30 22:31:24 UTC
Update Date2020-06-04 21:59:04 UTC
BMDB IDBMDB0000482
Secondary Accession Numbers
  • BMDB00482
Metabolite Identification
Common NameCaprylic acid
DescriptionCaprylic acid, also known as 8:0 or octylic acid, belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms. Caprylic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Caprylic acid exists in all living species, ranging from bacteria to humans. Caprylic acid participates in a number of enzymatic reactions, within cattle. In particular, Caprylic acid can be biosynthesized from trans-2-octenoic acid; which is mediated by the enzyme fatty acid synthase. enoyl reductase domain. In addition, Caprylic acid and malonic acid can be converted into 3-oxodecanoic acid through its interaction with the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In cattle, caprylic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Caprylic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
1-Heptanecarboxylic acidChEBI
8:0ChEBI
Acide octanoiqueChEBI
Acido octanoicoChEBI
Acidum octanociumChEBI
Acidum octanoicumChEBI
C8:0ChEBI
CH3-[CH2]6-COOHChEBI
KaprylsaeureChEBI
N-Caprylic acidChEBI
N-Octanoic acidChEBI
N-Octoic acidChEBI
N-Octylic acidChEBI
OCTANOIC ACID (caprylIC ACID)ChEBI
OctansaeureChEBI
Octoic acidChEBI
Octylic acidChEBI
OctanoateKegg
1-HeptanecarboxylateGenerator
N-CaprylateGenerator
N-OctanoateGenerator
N-OctoateGenerator
N-OctylateGenerator
OCTANOate (caprylate)Generator
OctoateGenerator
OctylateGenerator
Octanoic acidGenerator
CaprylateGenerator
Emery 657HMDB
Kortacid 0899HMDB
Lunac 8-95HMDB
Lunac 8-98HMDB
Neo-fat 8HMDB
Neo-fat 8SHMDB
Prifac 2901HMDB
Caprylic acid, cadmium saltHMDB
Caprylic acid, cesium saltHMDB
Caprylic acid, manganese saltHMDB
Caprylic acid, nickel(+2) saltHMDB
Caprylic acid, zinc saltHMDB
Caprylic acid, aluminum saltHMDB
Caprylic acid, barium saltHMDB
Caprylic acid, chromium(+2) saltHMDB
Caprylic acid, lead(+2) saltHMDB
Caprylic acid, potassium saltHMDB
Caprylic acid, tin(+2) saltHMDB
Sodium octanoateHMDB
Caprylic acid, 14C-labeledHMDB
Caprylic acid, lithium saltHMDB
Caprylic acid, ruthenium(+3) saltHMDB
Caprylic acid, sodium saltHMDB
Caprylic acid, sodium salt, 11C-labeledHMDB
Caprylic acid, tin saltHMDB
Caprylic acid, zirconium saltHMDB
Sodium caprylateHMDB
Caprylic acid, ammonia saltHMDB
Caprylic acid, calcium saltHMDB
Caprylic acid, cobalt saltHMDB
Caprylic acid, copper saltHMDB
Caprylic acid, copper(+2) saltHMDB
Caprylic acid, iridum(+3) saltHMDB
Caprylic acid, iron(+3) saltHMDB
Caprylic acid, lanthanum(+3) saltHMDB
Caprylic acid, zirconium(+4) saltHMDB
FA(8:0)HMDB
Lithium octanoateHMDB
Chemical FormulaC8H16O2
Average Molecular Weight144.2114
Monoisotopic Molecular Weight144.115029756
IUPAC Nameoctanoic acid
Traditional Namecaprylic acid
CAS Registry Number124-07-2
SMILES
CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C8H16O2/c1-2-3-4-5-6-7-8(9)10/h2-7H2,1H3,(H,9,10)
InChI KeyWWZKQHOCKIZLMA-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point16.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.789 mg/mLNot Available
LogP3.05HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP2.92ALOGPS
logP2.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)5.19ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity40.28 m³·mol⁻¹ChemAxon
Polarizability17.4 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0910000000-e609d5de69ede6fbcde0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0gb9-1920000000-1dc6ed976e003f99e23dView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03kc-9000000000-74cfce03769b41313952View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uyi-0931100000-7668e36e436054042b5cView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-e609d5de69ede6fbcde0View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-1920000000-1dc6ed976e003f99e23dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0910000000-9ecb4ccb46e89710f76aView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9100000000-8854c56056d8d3405087View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-062l-9100000000-67da39159980b9078fabView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-0900000000-bb237630bedcee6145d1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-2900000000-98284f50a271878c8481View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-5900000000-209fbbacd4996b9a770dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03kc-9000000000-74cfce03769b41313952View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-e2c4dff10393086340f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-1900000000-bbde8564b4e5543a636aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Negativesplash10-0006-0900000000-d219a0c6559a4783fd81View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-e2c4dff10393086340f7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-bbde8564b4e5543a636aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0006-0900000000-ca22ecd0b25fa371fc73View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0gvp-9100000000-58c00a2024ba0bae4ff4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-2505e6738cf5d5877654View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-1ab4cdf8f74c93312743View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-2900000000-ac7c80e50c93b8cc3af7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9400000000-d2694b5f89d8eaeb2ab1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-f2b24072c91d8b0e4078View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-ad62d44e72f4dd1760abView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-7900000000-9c869b84815f21dffc7cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-b8a648d443695914e479View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6u-9100000000-f5c38fdad70b324e75acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-bee103956686b4840d1eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-e7cbd036c8e80018c825View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-8f2b048da6331570976cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-cd31ca01a5fa6be86acbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-682c215be5abe1fe87edView in MoNA
MSMass Spectrum (Electron Ionization)splash10-03kc-9000000000-8c7db9a9d75b2cc1bd1cView in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Epidermis
  • Milk
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Laura Evans, Stua...
details
EpidermisExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
MilkDetected and Quantified10.5 +/- 0.4 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12.92 +/- 6.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified13.4 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1594.88 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1386.85 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified277.371 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1317.51 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10.2 +/- 0.2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified277.371 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3397.79 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3328.45 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3120.42 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified8.8 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified16 +/- 3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified11 +/- 2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified14.11 +/- 1.28 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified14 +/- 4 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified12.83 +/- 2.57 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified3.85 +/- 0.77 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified4.11 +/- 1.026 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified12.9 +/- 0.02 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
MilkDetected and Quantified4853.999 +/- 2080.285 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified17.682 +/- 0.42 uMNot SpecifiedNot Specified
Normal
    • Catrienus De Jong...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Kurt J. Boudonck,...
details
MilkDetected and Quantified23.01 +/- 8.03 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified3536.485 +/- 832.114 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified3397.799 +/- 693.428 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Lawrence K. Cream...
details
MilkDetected and Quantified14.23 +/- 6.69 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified0.8 (0.6 - 1.6) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
MilkDetected and Quantified0.8 (0.6 - 1.4) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
MilkDetected and Quantified0.8 (0.6 - 1.7) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
MilkDetected and Quantified5.6 (0.8 - 10.6) uMNot SpecifiedNot Specified
Normal
    • Harper, W. J., Go...
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000482
DrugBank IDDB04519
Phenol Explorer Compound IDNot Available
FooDB IDFDB003336
KNApSAcK IDC00001231
Chemspider ID370
KEGG Compound IDC06423
BioCyc IDCPD-195
BiGG ID48223
Wikipedia LinkCaprylic_acid
METLIN ID5469
PubChem Compound379
PDB IDNot Available
ChEBI ID28837
References
Synthesis ReferenceCaprylic acid. Jpn. Kokai Tokkyo Koho (1983), 4 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Soyeurt H, Dardenne P, Dehareng F, Lognay G, Veselko D, Marlier M, Bertozzi C, Mayeres P, Gengler N: Estimating fatty acid content in cow milk using mid-infrared spectrometry. J Dairy Sci. 2006 Sep;89(9):3690-5. doi: 10.3168/jds.S0022-0302(06)72409-2. [PubMed:16899705 ]
  2. Jensen RG: The composition of bovine milk lipids: January 1995 to December 2000. J Dairy Sci. 2002 Feb;85(2):295-350. doi: 10.3168/jds.S0022-0302(02)74079-4. [PubMed:11913692 ]
  3. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
  4. Colman E, Fokkink WB, Craninx M, Newbold JR, De Baets B, Fievez V: Effect of induction of subacute ruminal acidosis on milk fat profile and rumen parameters. J Dairy Sci. 2010 Oct;93(10):4759-73. doi: 10.3168/jds.2010-3158. [PubMed:20855010 ]
  5. GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
  6. O'Callaghan TF, Vazquez-Fresno R, Serra-Cayuela A, Dong E, Mandal R, Hennessy D, McAuliffe S, Dillon P, Wishart DS, Stanton C, Ross RP: Pasture Feeding Changes the Bovine Rumen and Milk Metabolome. Metabolites. 2018 Apr 6;8(2). pii: metabo8020027. doi: 10.3390/metabo8020027. [PubMed:29642378 ]
  7. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
  8. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  9. M. Ferrand, B. Huquet. S. Barbey, F. Barillet, F. Faucon, H. Larroque, O. Leray, J.M. Trommenschlager, M. Brochard (2011). M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189. Chemometrics and Intelligent Laboratory Systems.
  10. Lawrence K. Creamer, Alastair K.H. MacGibbon (1996). Lawrence K. Creamer, Alastair K.H. MacGibbon. Some recent advances in the basic chemistry of milk proteins and lipids. International Dairy J. (1996) 6(6):539-568 doi: 10.1016/0958-6946(96)85309-X. International Dairy Journal.
  11. A. Foroutan et al. (2019). A. Foroutan et al. The Chemical Composition of Commercial Cow's Milk (in preparation). Journal of Agricultural and Food Chemistry.
  12. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities as an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
Q71SP7
Molecular weight:
274554.0
Reactions
trans-2-Octenoic acid → Caprylic aciddetails
Caprylic acid + Malonic acid → 3-Oxodecanoic aciddetails