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Identification
YMDB IDYMDB00678
Namelauric acid
SpeciesSaccharomyces cerevisiae
StrainBrewer's yeast
DescriptionDodecanoic acid, also known as dodecanoate or lauric 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. Dodecanoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Dodecanoic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 1-Undecanecarboxylate
  • 1-Undecanecarboxylic acid
  • ABL
  • Acide Laurique
  • C12 fatty acid
  • C12:0
  • Coconut oil fatty acids
  • DAO
  • Dodecanoate
  • dodecanoic acid
  • dodecoate
  • Dodecoic acid
  • Dodecylate
  • dodecylcarboxylate
  • Dodecylic acid
  • duodecyclate
  • Duodecyclic acid
  • duodecylate
  • Duodecylic acid
  • LAP
  • LAU
  • Laurate
  • Lauric acid
  • Laurinsaeure
  • Laurostearate
  • Laurostearic acid
  • MYR
  • n-Dodecanoate
  • n-Dodecanoic acid
  • Sorbitan laurate
  • Sorbitan monolaurate (NF)
  • undecane-1-carboxylate
  • Undecane-1-carboxylic acid
  • Vulvate
  • Vulvic acid
  • CH3-[CH2]10-COOH
  • Dodecylcarboxylic acid
  • Laate
  • Laic acid
  • Aliphat no. 4
  • Edenor C 1298-100
  • Emery 651
  • Hystrene 9512
  • Kortacid 1299
  • Lunac L 70
  • Lunac L 98
  • Neo-fat 12
  • Neo-fat 12-43
  • Nissan naa 122
  • Philacid 1200
  • Prifac 2920
  • Univol u 314
  • Lauric acid, nickel(2+) salt
  • Sodium dodecanoate
  • Lauric acid, lithium salt
  • Lauric acid, sodium salt
  • Lauric acid, ammonium salt
  • Lauric acid, magnesium salt
  • Lauric acid, potassium salt
  • Potassium laurate
  • Lauric acid, barium and cadmium salt (4:1:1)
  • Lauric acid, calcium salt
  • Sodium laurate
CAS number143-07-7
WeightAverage: 200.3178
Monoisotopic: 200.177630012
InChI KeyPOULHZVOKOAJMA-UHFFFAOYSA-N
InChIInChI=1S/C12H24O2/c1-2-3-4-5-6-7-8-9-10-11-12(13)14/h2-11H2,1H3,(H,13,14)
IUPAC Namedodecanoic acid
Traditional IUPAC Namelauric acid
Chemical FormulaC12H24O2
SMILESCCCCCCCCCCCC(O)=O
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
Physical Properties
StateLiquid
Charge0
Melting point44-46 °C
Experimental Properties
PropertyValueReference
Water Solubility0.00481 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP4.60 [SANGSTER (1993)]PhysProp
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 Area37.3 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity58.68 m³·mol⁻¹ChemAxon
Polarizability25.85 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cell Envelope
  • Cytoplasm
  • Endoplasmic Reticulum
  • Extracellular
  • Lipid Particle
  • Mitochondrion
  • Peroxisome
Organoleptic Properties
Flavour/OdourSource
Bay oilFDB003010
CoconutFDB003010
FattyFDB003010
MetalFDB003010
MildFDB003010
SMPDB Pathways
Cholesterol biosynthesis and metabolism CE(12:0)PW002548 ThumbThumb?image type=greyscaleThumb?image type=simple
Fatty acid biosynthesisPW002458 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Fatty acid biosynthesisec00061 Map00061
SMPDB Reactions
lauric acid + Malonate3-Oxotetradecanoic acid
trans-Dodec-2-enoic acidlauric acid
KEGG Reactions
capric acid + malonyl-CoA + hydron + NADPHlauric acid + Carbon dioxide + NADP + water + Coenzyme A
lauric acid + malonyl-CoA + hydron + NADPHCarbon dioxide + NADP + myristic acid + water + Coenzyme A
lauric acid + hydron + malonyl-CoA + oxygen + NADPHNADP + Carbon dioxide + Myristoleic acid + Coenzyme A + water
lauric acid + Adenosine triphosphate + Coenzyme AAdenosine monophosphate + Pyrophosphate + lauroyl-CoA
water + lauroyl-[acyl-carrier protein] ↔ lauric acid + acyl-carrier protein + hydron
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0159-0910000000-a12b321a54a44ae28972JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-014i-2910000000-d52410168e784872a5a6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-06xx-9100000000-1ef5cd411f38c53a0a92JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0706-9100000000-e66a9147257053b93702JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0706-9100000000-2dd666a9a0355b1ca144JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-074i-9300000000-405ec308fe8c935c62a2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-067i-0930000000-6a80d41e346f4b10104cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-a12b321a54a44ae28972JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-014i-2910000000-d52410168e784872a5a6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-1910000000-8246864bf316bce609a2JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9500000000-e05832f94ff0361363a2JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05g0-9310000000-038e232cccb44582ec9cJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-2290000000-861c4b7b2da35b82ef7fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0a4l-9100000000-966cf4c6621fcec41368JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-054o-9000000000-d43dd32656ad22e95fddJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-06xx-9100000000-a71409efaf5fdd6ab0e1JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positivesplash10-0706-9100000000-eb09296a8c4c7c381b38JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-f22d8298d64e6f382279JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-0900000000-4bb88d3b1d2b7ac88152JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-0900000000-0c79a7257b53685108c6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0002-9600000000-25d268515337ef276c60JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-009b-9000000000-c00963f9b91f4a82e1efJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-f22d8298d64e6f382279JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-4bb88d3b1d2b7ac88152JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-0c79a7257b53685108c6JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0920000000-63cd88b9477cd281d342JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5c-4910000000-94738a1f436dcf1abcedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-07ca8cffe5ba2f9f920dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0920000000-63cd88b9477cd281d342JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a5c-4910000000-94738a1f436dcf1abcedJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9100000000-07ca8cffe5ba2f9f920dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-1655e63166b4d9dd4f59JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-1900000000-7c55a9ca2b49d4920029JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-ed8f6bcf96c68ac84738JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0900000000-1655e63166b4d9dd4f59JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0532-1900000000-7c55a9ca2b49d4920029JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-ed8f6bcf96c68ac84738JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-074l-9100000000-911a01d38925d0de481fJSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Jones, J. M., Nau, K., Geraghty, M. T., Erdmann, R., Gould, S. J. (1999). "Identification of peroxisomal acyl-CoA thioesterases in yeast and humans." J Biol Chem 274:9216-9223.10092594
  • Schneiter, R., Tatzer, V., Gogg, G., Leitner, E., Kohlwein, S. D. (2000). "Elo1p-dependent carboxy-terminal elongation of C14:1Delta(9) to C16:1Delta(11) fatty acids in Saccharomyces cerevisiae." J Bacteriol 182:3655-3660.10850979
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.
External Links:
ResourceLink
CHEBI ID18262
HMDB IDHMDB00638
Pubchem Compound ID3893
Kegg IDC02679
ChemSpider ID3756
FOODB IDFDB003010
WikipediaLauric_acid
BioCyc IDDODECANOATE

Enzymes

General function:
Involved in fatty acid elongase activity
Specific function:
May be a membrane bound enzyme involved in the highly specific elongation of saturated 14-carbon fatty acids (14:0) to 16-carbon species (16:0)
Gene Name:
ELO1
Uniprot ID:
P39540
Molecular weight:
36233.60156
Reactions
Acyl-CoA + malonyl-CoA → 3-oxoacyl-CoA + CoA + CO(2).
General function:
Involved in catalytic activity
Specific function:
Esterification, concomitant with transport, of endogenous long-chain fatty acids into metabolically active CoA thioesters for subsequent degradation or incorporation into phospholipids. Preferentially acts on C9:0-C13:0 fatty acids although C7:0-C17:0 fatty acids are tolerated
Gene Name:
FAA2
Uniprot ID:
P39518
Molecular weight:
83437.10156
Reactions
ATP + a long-chain carboxylic acid + CoA → AMP + diphosphate + an acyl-CoA.
General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long- chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. The beta subunit contains domains for:[acyl-carrier-protein] acetyltransferase and malonyltransferase, S-acyl fatty acid synthase thioesterase, enoyl-[acyl-carrier-protein] reductase, and 3-hydroxypalmitoyl-[acyl-carrier-protein] dehydratase
Gene Name:
FAS1
Uniprot ID:
P07149
Molecular weight:
228689.0
Reactions
Acetyl-CoA + n malonyl-CoA + 2n NADH + 2n NADPH → long-chain-acyl-CoA + n CoA + n CO(2) + 2n NAD(+) + 2n NADP(+).
Acetyl-CoA + [acyl-carrier-protein] → CoA + acetyl-[acyl-carrier-protein].
Malonyl-CoA + [acyl-carrier-protein] → CoA + malonyl-[acyl-carrier-protein].
(3R)-3-hydroxypalmitoyl-[acyl-carrier-protein] → hexadec-2-enoyl-[acyl-carrier-protein] + H(2)O.
Acyl-[acyl-carrier-protein] + NAD(+) → trans-2,3-dehydroacyl-[acyl-carrier-protein] + NADH.
Oleoyl-[acyl-carrier-protein] + H(2)O → [acyl-carrier-protein] + oleate.
General function:
Involved in acyl-CoA thioesterase activity
Specific function:
Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH
Gene Name:
TES1
Uniprot ID:
P41903
Molecular weight:
40259.39844
Reactions
Palmitoyl-CoA + H(2)O → CoA + palmitate.