Milk Composition Database: Showing metabocard for Dodecanoic acid (BMDB0000638)

Identification Taxonomy Physical properties Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:34:04 UTC

Update Date

2020-06-04 22:49:43 UTC

MCDB ID

BMDB0000638

Secondary Accession Numbers

BMDB00638

Metabolite Identification

Common Name

Dodecanoic acid

Description

Dodecanoic acid, also known as dodecanoate or potassium laurate, 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. Dodecanoic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Dodecanoic acid exists in all living species, ranging from bacteria to humans. Dodecanoic acid participates in a number of enzymatic reactions, within cattle. In particular, Dodecanoic acid and coenzyme A can be converted into lauroyl-CoA and L-carnitine; which is catalyzed by the enzyme carnitine O-palmitoyltransferase 2, mitochondrial. In addition, Dodecanoic acid can be converted into dodecanoic acid; which is catalyzed by the enzyme peroxisomal membrane protein 11C. In cattle, dodecanoic acid is involved in the metabolic pathway called the Beta oxidation OF very long chain fatty acids pathway. Dodecanoic acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Undecanecarboxylic acid	ChEBI
ABL	ChEBI
C12 Fatty acid	ChEBI
C12:0	ChEBI
CH3-[CH2]10-COOH	ChEBI
Coconut oil fatty acids	ChEBI
DAO	ChEBI
Dodecoic acid	ChEBI
Dodecylcarboxylate	ChEBI
Dodecylic acid	ChEBI
Duodecyclic acid	ChEBI
Duodecylic acid	ChEBI
Lauric acid	ChEBI
Laurinsaeure	ChEBI
Laurostearic acid	ChEBI
N-Dodecanoic acid	ChEBI
Undecane-1-carboxylic acid	ChEBI
Vulvic acid	ChEBI
Dodecanoate	Kegg
1-Undecanecarboxylate	Generator
Dodecoate	Generator
Dodecylcarboxylic acid	Generator
Dodecylate	Generator
Duodecyclate	Generator
Duodecylate	Generator
Laate	Generator
Laic acid	Generator
Laurostearate	Generator
N-Dodecanoate	Generator
Undecane-1-carboxylate	Generator
Vulvate	Generator
Aliphat no. 4	HMDB
Edenor C 1298-100	HMDB
Emery 651	HMDB
Hystrene 9512	HMDB
Kortacid 1299	HMDB
Laurate	HMDB
Lunac L 70	HMDB
Lunac L 98	HMDB
Neo-fat 12	HMDB
Neo-fat 12-43	HMDB
Nissan naa 122	HMDB
Philacid 1200	HMDB
Prifac 2920	HMDB
Univol u 314	HMDB
1-Dodecanoic acid	HMDB
FA(12:0)	HMDB
Dodecanoic acid	PhytoBank

Chemical Formula

C₁₂H₂₄O₂

Average Molecular Weight

200.3178

Monoisotopic Molecular Weight

200.177630012

IUPAC Name

dodecanoic acid

Traditional Name

lauric acid

CAS Registry Number

143-07-7

SMILES

CCCCCCCCCCCC(O)=O

InChI Identifier

InChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)

InChI Key

POULHZVOKOAJMA-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:30805 )
straight-chain saturated fatty acid (CHEBI:30805 )
Straight chain fatty acids (C02679 )
Saturated fatty acids (C02679 )
Straight chain fatty acids (LMFA01010012 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	44 - 46 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0048 mg/mL	Not Available
LogP	4.6	SANGSTER (1993)

Predicted Properties

Property	Value	Source
logP	5.13	ALOGPS
logP	4.48	ChemAxon
logS	-4.3	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	10	ChemAxon
Refractivity	58.68 m³·mol⁻¹	ChemAxon
Polarizability	25.85 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-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0159-0910000000-a12b321a54a44ae28972	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-014i-2910000000-d52410168e784872a5a6	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-06xx-9100000000-1ef5cd411f38c53a0a92	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0706-9100000000-e66a9147257053b93702	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0706-9100000000-2dd666a9a0355b1ca144	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-074i-9300000000-405ec308fe8c935c62a2	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-067i-0930000000-6a80d41e346f4b10104c	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-a12b321a54a44ae28972	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-2910000000-d52410168e784872a5a6	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-1910000000-8246864bf316bce609a2	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-e05832f94ff0361363a2	2016-09-22	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05g0-9310000000-038e232cccb44582ec9c	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)	splash10-0udi-2290000000-861c4b7b2da35b82ef7f	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4l-9100000000-966cf4c6621fcec41368	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-054o-9000000000-d43dd32656ad22e95fdd	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-06xx-9100000000-a71409efaf5fdd6ab0e1	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positive	splash10-0706-9100000000-eb09296a8c4c7c381b38	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-f22d8298d64e6f382279	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-0900000000-4bb88d3b1d2b7ac88152	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-0900000000-0c79a7257b53685108c6	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9600000000-25d268515337ef276c60	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-009b-9000000000-c00963f9b91f4a82e1ef	2012-08-31	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-f22d8298d64e6f382279	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-4bb88d3b1d2b7ac88152	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-0c79a7257b53685108c6	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0920000000-63cd88b9477cd281d342	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5c-4910000000-94738a1f436dcf1abced	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-07ca8cffe5ba2f9f920d	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0920000000-63cd88b9477cd281d342	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5c-4910000000-94738a1f436dcf1abced	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-07ca8cffe5ba2f9f920d	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-1655e63166b4d9dd4f59	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0532-1900000000-7c55a9ca2b49d4920029	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-ed8f6bcf96c68ac84738	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-1655e63166b4d9dd4f59	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0532-1900000000-7c55a9ca2b49d4920029	2015-05-27	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-ed8f6bcf96c68ac84738	2015-05-27	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-074l-9100000000-911a01d38925d0de481f	2014-09-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, 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	5991 +/- 1996 uM	Total fatty acid	PMID: 16899705	details
Detected but not Quantified	Not Applicable		Kurt J. Boudonck,...	details
Detected and Quantified	6689 +/- 2147 uM	Total fatty acid	M. Ferrand et al....	details
Detected and Quantified	6190 +/- 1847 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	2446 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	2496 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	599 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	1297 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	599 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	6689 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	6290 uM	Total fatty acid	Fooddata+, T...	details
Detected and Quantified	5741 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	33946 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	41434 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	43431 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	53914 uM	Total fatty acid	M.J. Abarghuei, Y...	details
Detected and Quantified	19.97 +/- 2.03 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	21.06 +/- 2.77 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	8.13 +/- 0.19 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	3.33 +/- 0.74 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	17.42 +/- 0.01 uM	Free fatty acid	Bashar Amer, Caro...	details
Detected and Quantified	26 +/- 1 uM	Free fatty acid	Catrienus De Jong...	details
Detected and Quantified	48.5 +/- 23.4 uM	Free fatty acid	PMID: 11754544	details
Detected and Quantified	19.4 +/- 6.6 uM	Free fatty acid	PMID: 11754544	details
Detected and Quantified	5.8 +/- 0.1 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	9.8 +/- 0.3 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	9.4 +/- 0.3 uM	Free fatty acid	PMID: 30994344	details
Detected and Quantified	10.2 +/- 0.2 uM	Free fatty acid	PMID: 30994344	details

External Links

HMDB ID

HMDB0000638

DrugBank ID

DB03017

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

30805

References

Synthesis Reference

Stepanova, G. A.; Markevich, V. S.; Garanin, V. I.; Stychinskii, G. F. Synthesis of lauric acid. Khimicheskaya Promyshlennost (Moscow, Russian Federation) (1974), (12), 930.

Material Safety Data Sheet (MSDS)

Not Available

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 ]
Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]
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.
Fooddata+, The Technical University of Denmark (DTU) [Link]

Showing metabocard for Dodecanoic acid (BMDB0000638)

Structure for BMDB0000638 (Dodecanoic acid)