Milk Composition Database: Showing metabocard for Capric acid (BMDB0000511)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

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Record Information

Version

1.0

Creation Date

2016-09-30 22:31:54 UTC

Update Date

2020-06-04 22:42:01 UTC

MCDB ID

BMDB0000511

Secondary Accession Numbers

BMDB00511

Metabolite Identification

Common Name

Capric acid

Description

Capric acid, also known as decanoate or 10:0, 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. Capric acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Capric acid exists in all living species, ranging from bacteria to humans. Capric acid participates in a number of enzymatic reactions, within cattle. In particular, Capric acid can be biosynthesized from trans-dec-2-enoic acid through its interaction with the enzyme fatty acid synthase. enoyl reductase domain. In addition, Capric acid and malonic acid can be converted into 3-oxododecanoic acid through the action of the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In cattle, capric acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Capric acid is a potentially toxic compound.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-Nonanecarboxylic acid	ChEBI
10:0	ChEBI
C10:0	ChEBI
Caprinic acid	ChEBI
CH3-[CH2]8-COOH	ChEBI
Decanoate	ChEBI
Decoic acid	ChEBI
Decylic acid	ChEBI
Dekansaeure	ChEBI
Kaprinsaeure	ChEBI
N-Capric acid	ChEBI
N-Decanoic acid	ChEBI
N-Decoic acid	ChEBI
N-Decylic acid	ChEBI
1-Nonanecarboxylate	Generator
Caprinate	Generator
Decanoic acid	Generator
Decoate	Generator
Decylate	Generator
N-Caprate	Generator
N-Decanoate	Generator
N-Decoate	Generator
N-Decylate	Generator
Caprate	Generator
Caprynate	HMDB
Caprynic acid	HMDB
Emery 659	HMDB
Lunac 10-95	HMDB
Lunac 10-98	HMDB
Prifac 2906	HMDB
Prifac 296	HMDB
Decanoic acid, sodium salt	HMDB
Sodium caprate	HMDB
Sodium decanoate	HMDB
FA(10:0)	HMDB

Chemical Formula

C₁₀H₂₀O₂

Average Molecular Weight

172.2646

Monoisotopic Molecular Weight

172.146329884

IUPAC Name

decanoic acid

Traditional Name

capric acid

CAS Registry Number

334-48-5

SMILES

CCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C10H20O2/c1-2-3-4-5-6-7-8-9-10(11)12/h2-9H2,1H3,(H,11,12)

InChI Key

GHVNFZFCNZKVNT-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:30813 )
straight-chain saturated fatty acid (CHEBI:30813 )
Straight chain fatty acids (C01571 )
Saturated fatty acids (C01571 )
Straight chain fatty acids (LMFA01010010 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	31.9 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.062 mg/mL	Not Available
LogP	4.09	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	3.93	ALOGPS
logP	3.59	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	4.95	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	8	ChemAxon
Refractivity	49.48 m³·mol⁻¹	ChemAxon
Polarizability	21.61 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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-MS (1 TMS)	splash10-017i-2920000000-7f6721f01b80a790d544	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-076u-9000000000-96a2e9e00e464db3c086	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-017i-2920000000-7f6721f01b80a790d544	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-016r-1910000000-1cc1026f6f325d994ab4	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-052g-9200000000-71a57b0e200e46fb66ed	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-00g0-9300000000-c615f39c0b907a00f67c	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, Positive (Annotated)	splash10-00di-0900000000-0a7f944302bce161f7e5	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-00b9-1900000000-b68efbceecf3433a9995	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-005a-9600000000-f2a54ed1a56ee9b7af77	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-076u-9000000000-96a2e9e00e464db3c086	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-00di-0900000000-771e7907916bf05e6b10	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00di-0900000000-f1e000384728ee06f802	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-1900000000-42a901bb54546da030da	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-004i-9000000000-83e77de04461ded1c4bc	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-004i-9000000000-f3190b828218d04d3cc7	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-014i-0000000910-e82208ed71b4a3735258	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-00di-0900000000-6ec01ce9b8fdc68d94a9	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-00di-0900000000-6ec01ce9b8fdc68d94a9	2017-08-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-00di-0900000000-8c6cdf0491f51ba6ef26	2017-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-856f34ef153b15cb3d1d	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0adi-4900000000-efb0bd73973bf0c317fd	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-d81148541fa575d32552	2015-04-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-99cd0519b210c46b4a4c	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fmi-1900000000-209285ec682ca47e1e5d	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-fb697080d761d0f48fe2	2015-04-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-856f34ef153b15cb3d1d	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0adi-4900000000-efb0bd73973bf0c317fd	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-d81148541fa575d32552	2015-05-26	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-99cd0519b210c46b4a4c	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0fmi-1900000000-209285ec682ca47e1e5d	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9300000000-fb697080d761d0f48fe2	2015-05-27	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-074l-9100000000-bf788cb34c09c6af56bf	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	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
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	2022-08-20	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Not Available	2012-12-05	View Spectrum

Concentrations

Status	Value		Reference	Details
Detected and Quantified	8127 +/- 3483 uM	Total fatty acid	PMID: 16899705	details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details
Detected and Quantified	6791 +/- 2031 uM	Total fatty acid	M. Ferrand et al....	details
Detected and Quantified	6385 +/- 1741 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: 11913692	details
Detected and Quantified	2670 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	2322 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	522 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	1393 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	522 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	6269 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	5921 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	5515 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	31347 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	37152 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	38894 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	45279 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	20 +/- 3 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	19 +/- 6 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	23 +/- 2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	25 +/- 1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	24 +/- 7.41 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	20 +/- 5.74 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	21 +/- 6 uM	Free fatty acid	PMID: 29642378	details
Detected and Quantified	18.26 +/- 2.36 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	19.76 +/- 2.58 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	6.87 +/- 0.86 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	5.16 +/- 0.86 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	17.01 +/- 0.05 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	22 +/- 1 uM	Free fatty acid	Catrienus De Jong...	details
Detected and Quantified	10.1 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	14.3 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	12.7 +/- 0.2 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	11.4 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details

External Links

HMDB ID

HMDB0000511

DrugBank ID

DB03600

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Decanoic acid

METLIN ID

336

PubChem Compound

2969

PDB ID

Not Available

ChEBI ID

30813

References

Synthesis Reference

Wang, Qin; Ni, Xindi; Shi, Jianying. Manufacturing technology of capric acid and hydroxyalkyl amide from Litsea cubeba nucleolus oil. Huaxue Shijie (1993), 34(2), 84-7.

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 ]
Keenan TW, Morre DJ, Olson DE, Yunghans WN, Patton S: Biochemical and morphological comparison of plasma membrane and milk fat globule membrane from bovine mammary gland. J Cell Biol. 1970 Jan;44(1):80-93. [PubMed:5409465 ]
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.
M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri (2014). M.J. Abarghuei, Y. Rouzbehan, A.Z.M Salem, M.J. Zamiri. Nitrogen balance, blood metabolites and milk fatty acid composition of dairy cows fed pomegranate-peel extract. Livestock Science (2014) 164:72-80 doi: 10.1016/j.livsci.2014.03.021. Livestock Science.
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 Capric acid (BMDB0000511)

Structure for BMDB0000511 (Capric acid)