Milk Composition Database: Showing metabocard for Caprylic acid (BMDB0000482)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:31:24 UTC

Update Date

2020-06-04 21:59:04 UTC

MCDB ID

BMDB0000482

Secondary Accession Numbers

BMDB00482

Metabolite Identification

Common Name

Caprylic acid

Description

Caprylic 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

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Heptanecarboxylic acid	ChEBI
8:0	ChEBI
Acide octanoique	ChEBI
Acido octanoico	ChEBI
Acidum octanocium	ChEBI
Acidum octanoicum	ChEBI
C8:0	ChEBI
CH3-[CH2]6-COOH	ChEBI
Kaprylsaeure	ChEBI
N-Caprylic acid	ChEBI
N-Octanoic acid	ChEBI
N-Octoic acid	ChEBI
N-Octylic acid	ChEBI
OCTANOIC ACID (caprylIC ACID)	ChEBI
Octansaeure	ChEBI
Octoic acid	ChEBI
Octylic acid	ChEBI
Octanoate	Kegg
1-Heptanecarboxylate	Generator
N-Caprylate	Generator
N-Octanoate	Generator
N-Octoate	Generator
N-Octylate	Generator
OCTANOate (caprylate)	Generator
Octoate	Generator
Octylate	Generator
Octanoic acid	Generator
Caprylate	Generator
Emery 657	HMDB
Kortacid 0899	HMDB
Lunac 8-95	HMDB
Lunac 8-98	HMDB
Neo-fat 8	HMDB
Neo-fat 8S	HMDB
Prifac 2901	HMDB
Caprylic acid, cadmium salt	HMDB
Caprylic acid, cesium salt	HMDB
Caprylic acid, manganese salt	HMDB
Caprylic acid, nickel(+2) salt	HMDB
Caprylic acid, zinc salt	HMDB
Caprylic acid, aluminum salt	HMDB
Caprylic acid, barium salt	HMDB
Caprylic acid, chromium(+2) salt	HMDB
Caprylic acid, lead(+2) salt	HMDB
Caprylic acid, potassium salt	HMDB
Caprylic acid, tin(+2) salt	HMDB
Sodium octanoate	HMDB
Caprylic acid, 14C-labeled	HMDB
Caprylic acid, lithium salt	HMDB
Caprylic acid, ruthenium(+3) salt	HMDB
Caprylic acid, sodium salt	HMDB
Caprylic acid, sodium salt, 11C-labeled	HMDB
Caprylic acid, tin salt	HMDB
Caprylic acid, zirconium salt	HMDB
Sodium caprylate	HMDB
Caprylic acid, ammonia salt	HMDB
Caprylic acid, calcium salt	HMDB
Caprylic acid, cobalt salt	HMDB
Caprylic acid, copper salt	HMDB
Caprylic acid, copper(+2) salt	HMDB
Caprylic acid, iridum(+3) salt	HMDB
Caprylic acid, iron(+3) salt	HMDB
Caprylic acid, lanthanum(+3) salt	HMDB
Caprylic acid, zirconium(+4) salt	HMDB
FA(8:0)	HMDB
Lithium octanoate	HMDB

Chemical Formula

C₈H₁₆O₂

Average Molecular Weight

144.2114

Monoisotopic Molecular Weight

144.115029756

IUPAC Name

octanoic acid

Traditional Name

caprylic acid

CAS Registry Number

124-07-2

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 Key

WWZKQHOCKIZLMA-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Medium-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 Framework

Aliphatic acyclic compounds

External Descriptors

medium-chain fatty acid (CHEBI:28837 )
straight-chain saturated fatty acid (CHEBI:28837 )
Straight chain fatty acids (C06423 )
Saturated fatty acids (C06423 )
Straight chain fatty acids (LMFA01010008 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	16.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.79 mg/mL	Not Available
LogP	3.05	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	2.92	ALOGPS
logP	2.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	5.19	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	40.28 m³·mol⁻¹	ChemAxon
Polarizability	17.4 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-0910000000-e609d5de69ede6fbcde0	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-0gb9-1920000000-1dc6ed976e003f99e23d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-03kc-9000000000-74cfce03769b41313952	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0uyi-0931100000-7668e36e436054042b5c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-e609d5de69ede6fbcde0	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gb9-1920000000-1dc6ed976e003f99e23d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014i-0910000000-9ecb4ccb46e89710f76a	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-9100000000-8854c56056d8d3405087	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-062l-9100000000-67da39159980b9078fab	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)	splash10-0006-0900000000-bb237630bedcee6145d1	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)	splash10-0006-2900000000-98284f50a271878c8481	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)	splash10-0006-5900000000-209fbbacd4996b9a770d	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-03kc-9000000000-74cfce03769b41313952	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0006-0900000000-e2c4dff10393086340f7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0006-1900000000-bbde8564b4e5543a636a	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - DI-ESI-Q-Exactive Plus , Negative	splash10-0006-0900000000-d219a0c6559a4783fd81	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-0900000000-e2c4dff10393086340f7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-1900000000-bbde8564b4e5543a636a	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-0006-0900000000-ca22ecd0b25fa371fc73	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0gvp-9100000000-58c00a2024ba0bae4ff4	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9300000000-2505e6738cf5d5877654	2021-09-20	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-1ab4cdf8f74c93312743	2021-09-20	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002b-2900000000-ac7c80e50c93b8cc3af7	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0002-9400000000-d2694b5f89d8eaeb2ab1	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-f2b24072c91d8b0e4078	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-1900000000-ad62d44e72f4dd1760ab	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-7900000000-9c869b84815f21dffc7c	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9000000000-b8a648d443695914e479	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a6u-9100000000-f5c38fdad70b324e75ac	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9000000000-bee103956686b4840d1e	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-e7cbd036c8e80018c825	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-8f2b048da6331570976c	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-cd31ca01a5fa6be86acb	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9100000000-682c215be5abe1fe87ed	2021-09-24	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-03kc-9000000000-8c7db9a9d75b2cc1bd1c	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Not Available	2014-09-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Not Available	2014-09-23	View Spectrum
1D NMR	¹H NMR Spectrum (1D, CDCl₃, experimental)	Not Available	2016-10-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, CDCl₃, experimental)	Not Available	2016-10-22	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CD₃OD, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	4854 +/- 2080 uM	Total fatty acid	PMID: 16899705	details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details
Detected and Quantified	3537 +/- 832 uM	Total fatty acid	M. Ferrand et al....	details
Detected and Quantified	3398 +/- 693 uM	Total fatty acid	M. Ferrand et al....	details
Detected but not Quantified	Not Applicable		PMID: 1779072	details
Detected but not Quantified	Not Applicable		PMID: 14168161	details
Detected but not Quantified	Not Applicable		PMID: 11913692	details
Detected and Quantified	1595 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	1387 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	277 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	1317 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	277 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	3398 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	3328 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	3120 uM	Total fatty acid	Fooddata+, T...	details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details
Detected but not Quantified	Not Applicable		Lawrence K. Cream...	details
Detected and Quantified	16 +/- 3 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	11 +/- 2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	12 +/- 1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	14 +/- 4 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	23 +/- 8.03 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	14 +/- 7 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	13 +/- 6.01 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	14.11 +/- 1.28 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	12.83 +/- 2.57 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	3.85 +/- 0.77 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	4.11 +/- 1.026 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	12.9 +/- 0.02 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	17 +/- 1 uM	Free fatty acid	Catrienus De Jong...	details
Detected and Quantified	0.8 (0.6 - 1.6) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	0.8 (0.6 - 1.4) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	0.8 (0.6 - 1.7) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	5.6 (0.8 - 10.6) uM	Free fatty acid	Harper, W. J., Go...	details
Detected and Quantified	10.5 +/- 0.4 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	13.4 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	10.2 +/- 0.2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	8.8 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details

External Links

HMDB ID

HMDB0000482

DrugBank ID

DB04519

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

28837

References

Synthesis Reference

Caprylic acid. Jpn. Kokai Tokkyo Koho (1983), 4 pp.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

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 ]
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 ]
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 ]
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 ]
GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
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 ]
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 ]
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.
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.
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.
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.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Caprylic acid (BMDB0000482)

Structure for BMDB0000482 (Caprylic acid)