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lauric acid (YMDB00678)

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
MOLSDFPDBSMILESInChI
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
  • 1-Dodecanoic acid
  • FA(12:0)
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 + Malonate → 3-Oxotetradecanoic acid
trans-Dodec-2-enoic acid → lauric acid
KEGG Reactions
capric acid + malonyl-CoA + hydron + NADPH → lauric acid + Carbon dioxide + NADP + water + Coenzyme A
lauric acid + malonyl-CoA + hydron + NADPH → Carbon dioxide + NADP + myristic acid + water + Coenzyme A
lauric acid + hydron + malonyl-CoA + oxygen + NADPH → NADP + Carbon dioxide + Myristoleic acid + Coenzyme A + water
lauric acid + Adenosine triphosphate + Coenzyme A ↔ Adenosine 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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
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

Protein Details
1. Elongation of fatty acids protein 1
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).
Protein Details
2. Long-chain-fatty-acid--CoA ligase 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.
Protein Details
3. Fatty acid synthase subunit beta
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.
Protein Details
4. Peroxisomal acyl-coenzyme A thioester hydrolase 1
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.