lauric acid (YMDB00678)

Identification

YMDB ID

YMDB00678

Name

lauric acid

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Dodecanoic 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

MOL SDF PDB SMILES InChI

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 number

143-07-7

Weight

Average: 200.3178
Monoisotopic: 200.177630012

InChI Key

POULHZVOKOAJMA-UHFFFAOYSA-N

InChI

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

IUPAC Name

dodecanoic acid

Traditional IUPAC Name

lauric acid

Chemical Formula

C₁₂H₂₄O₂

SMILES

CCCCCCCCCCCC(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.

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

Liquid

Charge

Melting point

44-46 °C

Experimental Properties

Property	Value	Reference
Water Solubility	0.00481 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	4.60 [SANGSTER (1993)]	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.01 g/L	ALOGPS
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	Yes	ChemAxon

Biological Properties

Cellular Locations

Cell Envelope
Cytoplasm
Endoplasmic Reticulum
Extracellular
Lipid Particle
Mitochondrion
Peroxisome

Organoleptic Properties

Flavour/Odour	Source
Bay oil	FDB003010
Coconut	FDB003010
Fatty	FDB003010
Metal	FDB003010
Mild	FDB003010

SMPDB Pathways

Cholesterol biosynthesis and metabolism CE(12:0)	PW002548
Fatty acid biosynthesis	PW002458

KEGG Pathways

Fatty acid biosynthesis

ec00061

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 Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	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	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (1 TMS)	splash10-014i-2910000000-d52410168e784872a5a6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-06xx-9100000000-1ef5cd411f38c53a0a92	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0706-9100000000-e66a9147257053b93702	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0706-9100000000-2dd666a9a0355b1ca144	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-074i-9300000000-405ec308fe8c935c62a2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-067i-0930000000-6a80d41e346f4b10104c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-0910000000-a12b321a54a44ae28972	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-014i-2910000000-d52410168e784872a5a6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0159-1910000000-8246864bf316bce609a2	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9500000000-e05832f94ff0361363a2	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05g0-9310000000-038e232cccb44582ec9c	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0udi-2290000000-861c4b7b2da35b82ef7f	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0a4l-9100000000-966cf4c6621fcec41368	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-054o-9000000000-d43dd32656ad22e95fdd	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-06xx-9100000000-a71409efaf5fdd6ab0e1	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - EI-B (JEOL JMS-AX-505-H) , Positive	splash10-0706-9100000000-eb09296a8c4c7c381b38	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-0002-0900000000-f22d8298d64e6f382279	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-0002-0900000000-4bb88d3b1d2b7ac88152	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-0002-0900000000-0c79a7257b53685108c6	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0002-9600000000-25d268515337ef276c60	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative	splash10-009b-9000000000-c00963f9b91f4a82e1ef	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-f22d8298d64e6f382279	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-4bb88d3b1d2b7ac88152	JSpectraViewer \| MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0002-0900000000-0c79a7257b53685108c6	JSpectraViewer \| MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0920000000-63cd88b9477cd281d342	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5c-4910000000-94738a1f436dcf1abced	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-07ca8cffe5ba2f9f920d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0920000000-63cd88b9477cd281d342	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a5c-4910000000-94738a1f436dcf1abced	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9100000000-07ca8cffe5ba2f9f920d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-1655e63166b4d9dd4f59	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0532-1900000000-7c55a9ca2b49d4920029	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-ed8f6bcf96c68ac84738	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0900000000-1655e63166b4d9dd4f59	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0532-1900000000-7c55a9ca2b49d4920029	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9400000000-ed8f6bcf96c68ac84738	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-074l-9100000000-911a01d38925d0de481f	JSpectraViewer \| MoNA
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	JSpectraViewer

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:

Resource	Link
CHEBI ID	18262
HMDB ID	HMDB00638
Pubchem Compound ID	3893
Kegg ID	C02679
ChemSpider ID	3756
FOODB ID	FDB003010
Wikipedia	Lauric_acid
BioCyc ID	DODECANOATE

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.

Structure for #<Compound:0xae79c634>

Enzymes

Reactions

Reactions

Reactions

Reactions