Record Information
Version1.0
Creation Date2016-09-30 22:36:51 UTC
Update Date2020-06-04 22:55:30 UTC
BMDB IDBMDB0000806
Secondary Accession Numbers
  • BMDB00806
Metabolite Identification
Common NameMyristic acid
DescriptionMyristic acid, also known as 14 or tetradecanoate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Myristic acid exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Myristic acid exists in all living species, ranging from bacteria to humans. Myristic acid participates in a number of enzymatic reactions, within cattle. In particular, Myristic acid can be biosynthesized from trans-tetra-dec-2-enoic acid through the action of the enzyme fatty acid synthase. enoyl reductase domain. In addition, Myristic acid and malonic acid can be converted into 3-oxohexadecanoic acid through the action of the enzyme fatty acid synthase. Beta ketoacyl synthase domain. In cattle, myristic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway. Myristic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
1-Tetradecanecarboxylic acidChEBI
14ChEBI
14:0ChEBI
14:00ChEBI
Acide tetradecanoiqueChEBI
C14ChEBI
CH3-[CH2]12-COOHChEBI
MyristinsaeureChEBI
N-Tetradecan-1-Oic acidChEBI
N-Tetradecanoic acidChEBI
N-Tetradecoic acidChEBI
Tetradecoic acidChEBI
TetradecanoateKegg
1-TetradecanecarboxylateGenerator
N-Tetradecan-1-OateGenerator
N-TetradecanoateGenerator
N-TetradecoateGenerator
TetradecoateGenerator
Tetradecanoic acidGenerator
MyristateGenerator
1-TridecanecarboxylateHMDB
1-Tridecanecarboxylic acidHMDB
CrodacidHMDB
Myristic acid pureHMDB
MyristoateHMDB
Myristoic acidHMDB
Tetradecanoic (myristic) acidHMDB
Acid, tetradecanoicHMDB
Acid, myristicHMDB
FA(14:0)HMDB
Chemical FormulaC14H28O2
Average Molecular Weight228.3709
Monoisotopic Molecular Weight228.20893014
IUPAC Nametetradecanoic acid
Traditional Namemyristic acid
CAS Registry Number544-63-8
SMILES
CCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)
InChI KeyTUNFSRHWOTWDNC-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-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 Point53.9 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.00107 mg/mLNot Available
LogP6.11SANGSTER (1993)
Predicted Properties
PropertyValueSource
logP6.1ALOGPS
logP5.37ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count12ChemAxon
Refractivity67.88 m³·mol⁻¹ChemAxon
Polarizability30.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-017i-2910000000-66b35fb8449ba9de9cd6View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-017i-2910000000-66b35fb8449ba9de9cd6View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-f45703c464ca75f98f26View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9700000000-ec8d81e37bc3b8531c99View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9330000000-5ec01705dfacc992be28View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-0090000000-73ac1cfb8731e6318cc5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004i-1090000000-3aa768974da0ea81c1c9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0090000000-22cd107a87b9acf058c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0090000000-2f7bb32e4b42206d851dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-2090000000-d45cffc15e2efbd45cd6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9200000000-dbca68238dfebab35251View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004r-9000000000-26827be8f8c2a4fbfd75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0006-0090000000-110165b889d231d09d59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0006-0090000000-110165b889d231d09d59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0006-0090000000-110165b889d231d09d59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0090000000-110165b889d231d09d59View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-91f4f874b25705464fb0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-15225a799e0a0bcff7c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0290000000-b88426a2003ceec57e30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-5940000000-6c73dc0032502abe4fc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-bde9bfcd2889066fc853View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0290000000-b88426a2003ceec57e30View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-5940000000-6c73dc0032502abe4fc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-bde9bfcd2889066fc853View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-a32f141c7b5af0bc4de1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1490000000-14bfb0d0344d7cf63443View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-512abb1322963024336fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-a32f141c7b5af0bc4de1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1490000000-14bfb0d0344d7cf63443View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-512abb1322963024336fView in MoNA
MSMass Spectrum (Electron Ionization)splash10-06xx-9200000000-4fdd41f0461ff5186901View in MoNA
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Adipose Tissue
  • Blood
  • Epidermis
  • Liver
  • Mammary Gland
  • Milk
  • Oocyte
  • Placenta
  • Prostate Tissue
  • Ruminal Fluid
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected and Quantified5136.47 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified4775.21 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified104050.78 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified132744.23 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified115186.7 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected and Quantified120872.0989 nmol/g of tissueNot SpecifiedNot Specified
Normal
    • C. Mapiye, T.D.Tu...
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected and Quantified151726.86 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected and Quantified140692.18 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected and Quantified147041.5 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected and Quantified138051.74 nmol/g of tissueNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
Adipose TissueDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
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 Quantified1926.69 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1445.0177 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified16814.752 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified16157.93 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified15107.00 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified10.5 +/- 0.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified14.4 +/- 0.3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified17.5 +/- 0.3 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified19 +/- 1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified35.64 +/- 6.48 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified41.48 +/- 6.48 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified17.52 +/- 1.14 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified7.14 +/- 0.65 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified30.39 +/- 0.20 uMNot SpecifiedNot Specified
Normal
    • Bashar Amer, Caro...
details
MilkDetected and Quantified17953.243 +/- 5254.608 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified39.585 +/- 0.59 uMNot SpecifiedNot Specified
Normal
    • Catrienus De Jong...
details
MilkDetected and Quantified84.5 +/- 26.1 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified53.5 +/- 15.7 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 but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified19660.990 +/- 4291.263 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected and Quantified19004.164 +/- 3809.591 uMNot SpecifiedNot Specified
Normal
    • M. Ferrand et al....
details
MilkDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
    • Lawrence K. Cream...
details
MilkDetected and Quantified6874.78 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified6568.26 uMNot SpecifiedNot Specified
Normal
details
MilkDetected and Quantified1445.0177 uMNot SpecifiedNot Specified
Normal
details
OocyteDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Normal
details
PlacentaExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Prostate TissueExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Ruminal FluidDetected and Quantified3.3 +/- 0.6 uMNot SpecifiedNot SpecifiedNormal
    • Fozia Saleem, Sou...
details
Ruminal FluidDetected and Quantified3.3 +/- 0.6 uMNot SpecifiedNot Specified
Normal
    • Fozia Saleem, Sou...
details
SpleenExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot Specified
Sub/clinical ketosis
details
HMDB IDHMDB0000806
DrugBank IDDB08231
Phenol Explorer Compound IDNot Available
FooDB IDFDB031009
KNApSAcK IDC00001228
Chemspider ID10539
KEGG Compound IDC06424
BioCyc IDCPD-7836
BiGG ID215851
Wikipedia LinkMyristic_acid
METLIN ID196
PubChem Compound11005
PDB IDNot Available
ChEBI ID28875
References
Synthesis ReferenceGreaves, W. S.; Linstead, R. P.; Shephard, B. R.; Thomas, S. L. S.; Weedon, B. C. L. Anodic syntheses. I. New syntheses of stearic, myristic, and other acids. Journal of the Chemical Society (1950), 3326-30.
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. GARTON GA: THE COMPOSITION AND BIOSYNTHESIS OF MILK LIPIDS. J Lipid Res. 1963 Jul;4:237-54. [PubMed:14168161 ]
  4. 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 ]
  5. 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.
  6. 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.
  7. 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.
  8. Fooddata+, The Technical University of Denmark (DTU) [Link]

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Reduces all-trans-retinal and 9-cis retinal. Can also catalyze the oxidation of all-trans-retinol with NADP as co-factor, but with much lower efficiency. Reduces alkyl phenyl ketones and alpha-dicarbonyl compounds with aromatic rings, such as pyrimidine-4-aldehyde, 3-benzoylpyridine, 4-benzoylpyridine, menadione and 4-hexanoylpyridine. Has no activity towards aliphatic aldehydes and ketones (By similarity).
Gene Name:
DHRS4
Uniprot ID:
Q8SPU8
Molecular weight:
29440.0
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-Tetra-dec-2-enoic acid → Myristic aciddetails
Myristic acid + Malonic acid → 3-Oxohexadecanoic aciddetails