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Record Information
Version1.0
Creation Date2016-09-30 22:31:24 UTC
Update Date2020-06-04 21:59:04 UTC
MCDB ID BMDB0000482
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
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point16.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.79 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0910000000-e609d5de69ede6fbcde02014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0gb9-1920000000-1dc6ed976e003f99e23d2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03kc-9000000000-74cfce03769b413139522017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0uyi-0931100000-7668e36e436054042b5c2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-e609d5de69ede6fbcde02017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0gb9-1920000000-1dc6ed976e003f99e23d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-0910000000-9ecb4ccb46e89710f76a2017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0596-9100000000-8854c56056d8d34050872016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-062l-9100000000-67da39159980b9078fab2017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-0900000000-bb237630bedcee6145d12012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-2900000000-98284f50a271878c84812012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-5900000000-209fbbacd4996b9a770d2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-03kc-9000000000-74cfce03769b413139522012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0006-0900000000-e2c4dff10393086340f72012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0006-1900000000-bbde8564b4e5543a636a2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Negativesplash10-0006-0900000000-d219a0c6559a4783fd812017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-0900000000-e2c4dff10393086340f72017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-1900000000-bbde8564b4e5543a636a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0006-0900000000-ca22ecd0b25fa371fc732017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0gvp-9100000000-58c00a2024ba0bae4ff42021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0002-9300000000-2505e6738cf5d58776542021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-1ab4cdf8f74c933127432021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002b-2900000000-ac7c80e50c93b8cc3af72016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9400000000-d2694b5f89d8eaeb2ab12016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9000000000-f2b24072c91d8b0e40782016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-ad62d44e72f4dd1760ab2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-7900000000-9c869b84815f21dffc7c2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-b8a648d443695914e4792016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6u-9100000000-f5c38fdad70b324e75ac2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-bee103956686b4840d1e2021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4l-9000000000-e7cbd036c8e80018c8252021-09-23View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-8f2b048da6331570976c2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-cd31ca01a5fa6be86acb2021-09-24View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9100000000-682c215be5abe1fe87ed2021-09-24View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03kc-9000000000-8c7db9a9d75b2cc1bd1c2014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Not Available2016-10-22View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not Available2012-12-05View Spectrum
Concentrations
StatusValueReferenceDetails
Detected and Quantified4854 +/- 2080 uMTotal fatty acid details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected and Quantified3537 +/- 832 uMTotal fatty acid
  • M. Ferrand et al....
details
Detected and Quantified3398 +/- 693 uMTotal fatty acid
  • M. Ferrand et al....
details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected and Quantified1595 uMTotal fatty acid details
Detected and Quantified1387 uMTotal fatty acid details
Detected and Quantified277 uMTotal fatty acid details
Detected and Quantified1317 uMTotal fatty acid details
Detected and Quantified277 uMTotal fatty acid details
Detected and Quantified3398 uMTotal fatty acid details
Detected and Quantified3328 uMTotal fatty acid details
Detected and Quantified3120 uMTotal fatty acid details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
details
Detected but not QuantifiedNot Applicable
  • Lawrence K. Cream...
details
Detected and Quantified16 +/- 3 uMFree fatty acid details
Detected and Quantified11 +/- 2 uMFree fatty acid details
Detected and Quantified12 +/- 1 uMFree fatty acid details
Detected and Quantified14 +/- 4 uMFree fatty acid details
Detected and Quantified23 +/- 8.03 uMFree fatty acid details
Detected and Quantified14 +/- 7 uMFree fatty acid details
Detected and Quantified13 +/- 6.01 uMFree fatty acid details
Detected and Quantified14.11 +/- 1.28 uMFree fatty acid
  • Bashar Amer, Caro...
details
Detected and Quantified12.83 +/- 2.57 uMFree fatty acid
  • Bashar Amer, Caro...
details
Detected and Quantified3.85 +/- 0.77 uMFree fatty acid
  • Bashar Amer, Caro...
details
Detected and Quantified4.11 +/- 1.026 uMFree fatty acid
  • Bashar Amer, Caro...
details
Detected and Quantified12.9 +/- 0.02 uMFree fatty acid
  • Bashar Amer, Caro...
details
Detected and Quantified17 +/- 1 uMFree fatty acid
  • Catrienus De Jong...
details
Detected and Quantified0.8 (0.6 - 1.6) uMFree fatty acid
  • Harper, W. J., Go...
details
Detected and Quantified0.8 (0.6 - 1.4) uMFree fatty acid
  • Harper, W. J., Go...
details
Detected and Quantified0.8 (0.6 - 1.7) uMFree fatty acid
  • Harper, W. J., Go...
details
Detected and Quantified5.6 (0.8 - 10.6) uMFree fatty acid
  • Harper, W. J., Go...
details
Detected and Quantified10.5 +/- 0.4 uMFree fatty acid details
Detected and Quantified13.4 +/- 0.1 uMFree fatty acid details
Detected and Quantified10.2 +/- 0.2 uMFree fatty acid details
Detected and Quantified8.8 +/- 0.1 uMFree fatty acid details
HMDB IDHMDB0000482
DrugBank IDDB04519
Phenol Explorer Compound IDNot Available
FoodDB 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)Download (PDF)
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]