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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2014-10-29 17:56:05 UTC
HMDB IDHMDB00638
Secondary Accession NumbersNone
Metabolite Identification
Common NameDodecanoic acid
DescriptionLauric acid, or dodecanoic acid is the main fatty acid in coconut oil and in palm kernel oil, and is believed to have antimicrobial properties. It is a white, powdery solid with a faint odor of bay oil. Lauric acid, although slightly irritating to mucous membranes, has a very low toxicity and so is used in many soaps and shampoos.
Structure
Thumb
Synonyms
  1. 1-Undecanecarboxylate
  2. 1-Undecanecarboxylic acid
  3. ABL
  4. Aliphat No. 4
  5. Dodecanoate
  6. Dodecanoic acid
  7. Dodecylate
  8. Dodecylic acid
  9. Edenor C 1298-100
  10. Emery 651
  11. Hystrene 9512
  12. Kortacid 1299
  13. Laurate
  14. Lauric acid
  15. Laurostearate
  16. Laurostearic acid
  17. Lunac L 70
  18. Lunac L 98
  19. N-Dodecanoate
  20. N-Dodecanoic acid
  21. Neo-Fat 12
  22. Neo-Fat 12-43
  23. Nissan NAA 122
  24. Philacid 1200
  25. Prifac 2920
  26. Univol U 314
  27. Vulvate
  28. Vulvic acid
Chemical FormulaC12H24O2
Average Molecular Weight200.3178
Monoisotopic Molecular Weight200.177630012
IUPAC Namedodecanoic acid
Traditional Namelauric acid
CAS Registry Number143-07-7
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 KeyPOULHZVOKOAJMA-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acids and Conjugates
Sub ClassStraight Chain Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Saturated fatty acids(KEGG)
  • Straight chain fatty acids(KEGG)
  • Straight chain fatty acids(Lipidmaps)
  • medium-chain fatty acid(ChEBI)
  • straight-chain saturated fatty acid(ChEBI)
Substituents
  • Carboxylic Acid
Direct ParentStraight Chain Fatty Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point44 - 46 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00481 mg/mLNot Available
LogP4.60SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.01 g/LALOGPS
logP5.13ALOGPS
logP4.48ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity58.68ChemAxon
Polarizability25.83ChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane (predicted from logP)
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Saliva
  • Urine
Tissue Location
  • Liver
  • Prostate
  • Stratum Corneum
  • Thyroid Gland
Pathways
NameSMPDB LinkKEGG Link
Beta Oxidation of Very Long Chain Fatty AcidsSMP00052map01040
Fatty Acid BiosynthesisSMP00456Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty AcidsSMP00481Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified12.0 (2.0-37.0) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified1.47 +/- 0.68 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified9.1 uMAdult (>18 years old)Not SpecifiedNormal details
BloodDetected and Quantified0.719 +/- 0.029 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified2.8 +/- 2.8 uMAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
    • Dame, ZT. et al. ...
details
UrineDetected and Quantified0.03 +/- 0.02 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothOral squamous cell carcinoma (OSCC) details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothOral leukoplakia (OLK) details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB03017
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003010
KNApSAcK IDC00001221
Chemspider ID3756
KEGG Compound IDC02679
BioCyc IDNot Available
BiGG ID40351
Wikipedia LinkDodecanoic acid
NuGOwiki LinkHMDB00638
Metagene LinkHMDB00638
METLIN ID5611
PubChem Compound3893
PDB IDDAO
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. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411
  2. Hoffmann GF, Meier-Augenstein W, Stockler S, Surtees R, Rating D, Nyhan WL: Physiology and pathophysiology of organic acids in cerebrospinal fluid. J Inherit Metab Dis. 1993;16(4):648-69. Pubmed: 8412012
  3. Amet Y, Berthou F, Fournier G, Dreano Y, Bardou L, Cledes J, Menez JF: Cytochrome P450 4A and 2E1 expression in human kidney microsomes. Biochem Pharmacol. 1997 Mar 21;53(6):765-71. Pubmed: 9113097
  4. Smith SW, Anderson BD: Human skin permeability enhancement by lauric acid under equilibrium aqueous conditions. J Pharm Sci. 1995 May;84(5):551-6. Pubmed: 7658343
  5. Powell PK, Wolf I, Lasker JM: Identification of CYP4A11 as the major lauric acid omega-hydroxylase in human liver microsomes. Arch Biochem Biophys. 1996 Nov 1;335(1):219-26. Pubmed: 8914854
  6. Ryan MT, Chopra RK: The paradoxical effect of fatty acid on steroid-albumin interaction. Biochim Biophys Acta. 1976 Mar 18;427(1):337-49. Pubmed: 1260006
  7. Amet Y, Berthou F, Baird S, Dreano Y, Bail JP, Menez JF: Validation of the (omega-1)-hydroxylation of lauric acid as an in vitro substrate probe for human liver CYP2E1. Biochem Pharmacol. 1995 Nov 27;50(11):1775-82. Pubmed: 8615855
  8. Kitahara T, Koyama N, Matsuda J, Aoyama Y, Hirakata Y, Kamihira S, Kohno S, Nakashima M, Sasaki H: Antimicrobial activity of saturated fatty acids and fatty amines against methicillin-resistant Staphylococcus aureus. Biol Pharm Bull. 2004 Sep;27(9):1321-6. Pubmed: 15340213
  9. NTP Toxicology and Carcinogenesis Studies of Lauric Acid Diethanolamine Condensate (CAS NO. 120-40-1) in F344/N Rats and B6C3F1 Mice (Dermal Studies). Natl Toxicol Program Tech Rep Ser. 1999 Jul;480:1-200. Pubmed: 12571683
  10. Amet Y, Berthou F, Menez JF: Simultaneous radiometric and fluorimetric detection of lauric acid metabolites using high-performance liquid chromatography following esterification with 4-bromomethyl-6,7-dimethoxycoumarin in human and rat liver microsomes. J Chromatogr B Biomed Appl. 1996 Jun 7;681(2):233-9. Pubmed: 8811432

Enzymes

General function:
Involved in phospholipase A2 activity
Specific function:
Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:
PLA2G2A
Uniprot ID:
P14555
Molecular weight:
16082.525
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in phospholipase A2 activity
Specific function:
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. L-alpha-1-palmitoyl-2-linoleoyl phosphatidylethanolamine is more efficiently hydrolyzed than the other phospholipids examined.
Gene Name:
PLA2G2D
Uniprot ID:
Q9UNK4
Molecular weight:
16546.1
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in acyltransferase activity
Specific function:
Beta-oxidation of fatty acids. The highest activity concerns the C6 to C10 chain length substrate. Converts the end product of pristanic acid beta oxidation, 4,8-dimethylnonanoyl-CoA, to its corresponding carnitine ester.
Gene Name:
CROT
Uniprot ID:
Q9UKG9
Molecular weight:
10213.63
General function:
Involved in acyltransferase activity
Specific function:
Not Available
Gene Name:
CPT2
Uniprot ID:
P23786
Molecular weight:
73776.335
General function:
Involved in zinc ion binding
Specific function:
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name:
ADH5
Uniprot ID:
P11766
Molecular weight:
39723.945
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in sphingolipid activator protein activity
Specific function:
Binds gangliosides and stimulates ganglioside GM2 degradation. It stimulates only the breakdown of ganglioside GM2 and glycolipid GA2 by beta-hexosaminidase A. It extracts single GM2 molecules from membranes and presents them in soluble form to beta-hexosaminidase A for cleavage of N-acetyl-D-galactosamine and conversion to GM3
Gene Name:
GM2A
Uniprot ID:
P17900
Molecular weight:
20838.1
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed: 17139284
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed: 17016423
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in ferric iron binding
Specific function:
The lactotransferrin transferrin-like domain 1 functions as a serine protease of the peptidase S60 family that cuts arginine rich regions. This function contributes to the antimicrobial activity
Gene Name:
LTF
Uniprot ID:
P02788
Molecular weight:
78181.2
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in protein binding
Specific function:
Cooperates with LY96 and CD14 to mediate the innate immune response to bacterial lipopolysaccharide (LPS). Acts via MYD88, TIRAP and TRAF6, leading to NF-kappa-B activation, cytokine secretion and the inflammatory response
Gene Name:
TLR4
Uniprot ID:
O00206
Molecular weight:
95679.2
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in transporter activity
Specific function:
Mediates the transport of acylcarnitines of different length across the mitochondrial inner membrane from the cytosol to the mitochondrial matrix for their oxidation by the mitochondrial fatty acid-oxidation pathway.
Gene Name:
SLC25A20
Uniprot ID:
O43772
Molecular weight:
32943.46
General function:
Involved in glycolipid transporter activity
Specific function:
Accelerates the intermembrane transfer of various glycolipids. Catalyzes the transfer of various glycosphingolipids between membranes but does not catalyze the transfer of phospholipids. May be involved in the intracellular translocation of glucosylceramides
Gene Name:
GLTP
Uniprot ID:
Q9NZD2
Molecular weight:
23849.6
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. Pubmed: 10592235
General function:
Involved in biosynthetic process
Specific function:
In fatty acid biosynthesis chain termination and release of the free fatty acid product is achieved by hydrolysis of the thio ester by a thioesterase I, a component of the fatty acid synthetase complex. The chain length of the released fatty acid is usually C16. However, in the mammary glands of non-ruminant mammals, and in the uropygial gland of certain waterfowl there exists a second thioesterase which releases medium-chain length fatty acids (C8 to C2) (By similarity).
Gene Name:
OLAH
Uniprot ID:
Q9NV23
Molecular weight:
29930.82
Reactions
Dodecanoyl-[acyl-carrier protein] + Water → Acyl-carrier protein + Dodecanoic aciddetails