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Record Information
Version1.0
Creation Date2016-09-30 22:34:04 UTC
Update Date2020-06-04 22:49:43 UTC
BMDB IDBMDB0000638
Secondary Accession Numbers
  • BMDB00638
Metabolite Identification
Common NameDodecanoic acid
DescriptionDodecanoic 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
Thumb
Synonyms
ValueSource
1-Undecanecarboxylic acidChEBI
ABLChEBI
C12 Fatty acidChEBI
C12:0ChEBI
CH3-[CH2]10-COOHChEBI
Coconut oil fatty acidsChEBI
DAOChEBI
Dodecoic acidChEBI
DodecylcarboxylateChEBI
Dodecylic acidChEBI
Duodecyclic acidChEBI
Duodecylic acidChEBI
Lauric acidChEBI
LaurinsaeureChEBI
Laurostearic acidChEBI
N-Dodecanoic acidChEBI
Undecane-1-carboxylic acidChEBI
Vulvic acidChEBI
DodecanoateKegg
1-UndecanecarboxylateGenerator
DodecoateGenerator
Dodecylcarboxylic acidGenerator
DodecylateGenerator
DuodecyclateGenerator
DuodecylateGenerator
LaateGenerator
Laic acidGenerator
LaurostearateGenerator
N-DodecanoateGenerator
Undecane-1-carboxylateGenerator
VulvateGenerator
Aliphat no. 4HMDB
Edenor C 1298-100HMDB
Emery 651HMDB
Hystrene 9512HMDB
Kortacid 1299HMDB
LaurateHMDB
Lunac L 70HMDB
Lunac L 98HMDB
Neo-fat 12HMDB
Neo-fat 12-43HMDB
Nissan naa 122HMDB
Philacid 1200HMDB
Prifac 2920HMDB
Univol u 314HMDB
1-Dodecanoic acidHMDB
FA(12:0)HMDB
Dodecanoic acidPhytoBank
Chemical FormulaC12H24O2
Average Molecular Weight200.3178
Monoisotopic Molecular Weight200.177630012
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number143-07-7
SMILESNot Available
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 KeyPOULHZVOKOAJMA-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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point44 - 46 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00481 mg/mLNot Available
LogP4.6SANGSTER (1993)
Predicted PropertiesNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Epidermis
  • Liver
  • Mammary Gland
  • Milk
  • Oocyte
  • Prostate Tissue
  • Thyroid Gland
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
LiverDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Mammary GlandDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified5.8 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified9.8 +/- 0.3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified9.4 +/- 0.3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified2446.11 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified2496.03 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified599.0481 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1297.938 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified599.0481 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified6689.37 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10.2 +/- 0.2 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified6290.01 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified5740.88 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified19.97 +/- 2.03 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified21.06 +/- 2.77 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified8.13 +/- 0.19 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified3.33 +/- 0.74 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified17.42 +/- 0.01 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified5990.475 +/- 1996.825 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified26.0586 +/- 0.42 uMNot SpecifiedNot Specified
Normal
    • Catrienus De Jong...
details
MilkDetected and Quantified48.5 +/- 23.4 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified19.4 +/- 6.6 uMNot SpecifiedNot Specified
Normal
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 Quantified6689.364 +/- 2146.587 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified6190.158 +/- 1847.0632 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Lawrence K. Cream...
details
MilkDetected and Quantified33946.0597 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified41434.161 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified43430.988 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
MilkDetected and Quantified53914.33 uMNot SpecifiedNot SpecifiedNormal
    • M.J. Abarghuei, Y...
details
OocyteDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Thyroid GlandExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
Not Available
HMDB IDHMDB0000638
DrugBank IDDB03017
Phenol Explorer Compound IDNot Available
FooDB IDFDB003010
KNApSAcK IDC00001221
Chemspider ID3756
KEGG Compound IDC02679
BioCyc IDDODECANOATE
BiGG ID40351
Wikipedia LinkLauric_acid
METLIN ID5611
PubChem Compound3893
PDB IDNot Available
ChEBI ID30805
References
Synthesis ReferenceStepanova, 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
  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. 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 ]
  6. 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 ]
  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. 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.
  12. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

General function:
Involved in carnitine O-octanoyltransferase activity
Specific function:
Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate.
Gene Name:
CROT
Uniprot ID:
O19094
Molecular weight:
70263.0
Reactions
Lauroyl-CoA → Coenzyme A + Dodecanoic aciddetails
General function:
Involved in carnitine O-palmitoyltransferase activity
Specific function:
Not Available
Gene Name:
CPT2
Uniprot ID:
Q2KJB7
Molecular weight:
74483.0
Reactions
Dodecanoic acid + Coenzyme A → Lauroyl-CoA + L-Carnitinedetails
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-Dodec-2-enoic acid → Dodecanoic aciddetails
Dodecanoic acid + Malonic acid → 3-Oxotetradecanoic aciddetails
General function:
Lipid transport and metabolism
Specific function:
Catalyzes the activation of fatty acids by CoA to produce an acyl-CoA, the first step in fatty acid metabolism (PubMed:11382754, PubMed:10561077). Capable of activating medium-chain fatty acids (e.g. butyric (C4) to decanoic (C10) acids), and certain carboxylate-containing xenobiotics, e.g. benzoate (PubMed:10561077, PubMed:11382754). Also catalyzes the activation of lipoate to lipoyl-nucleoside monophosphate (PubMed:11382754). Activates lipoate with GTP at a 1000-fold higher rate than with ATP and activates both (R)- and (S)-lipoate to the respective lipoyl-GMP, with a preference for (R)-lipoate (PubMed:11382754).
Gene Name:
ACSM1
Uniprot ID:
Q9BEA2
Molecular weight:
64923.0
Reactions
Dodecanoic acid + Adenosine triphosphate + Coenzyme A → Lauroyl-CoA + Adenosine monophosphate + Pyrophosphatedetails
General function:
Involved in G-protein coupled receptor activity
Specific function:
Receptor for medium-chain free fatty acid (FFA) with carbon chain lengths of C9 to C14. Capric acid (C10:0), undecanoic acid (C11:0) and lauric acid (C12:0) are the most potent agonists. Not activated by short-chain and long-chain saturated and unsaturated FFAs. Activation by medium-chain free fatty acid is coupled to a pertussis toxin sensitive G(i/o) protein pathway. May have important roles in processes from fatty acid metabolism to regulation of the immune system (By similarity).
Gene Name:
GPR84
Uniprot ID:
Q2KI97
Molecular weight:
43517.0