Record Information
Version1.0
Creation date2010-04-08 22:05:34 UTC
Update date2020-09-17 15:42:29 UTC
Primary IDFDB002890
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTetradecanoic acid
DescriptionMyristic acid, also known as tetradecanoic acid or C14:0, 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 is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. It has a waxy, fatty or soapy odor and a fatty, creamy or cheesy taste. Myristic acid exists in all living species, ranging from bacteria to humans. Myristic acid is a naturally occurring saturated fatty acid found in most animal and vegetable fats. Some of the highest levels of myristic acid are found in nutmeg. In particular, nutmeg butter has 75% trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butterfat, 8–14% of bovine milk, and 8.6% of breast milk as well as being a minor component of many other animal fats. It also comprises 14.49% of the fats from the fruit of the Durian species. Industrially myristic acid is used as an ingredient in soaps and cosmetics (From Dorland, 28th ed). In many eukaryotes (including humans), myristic acid is commonly added to the N-terminal glycine residue in receptor-associated kinases to confer membrane localization of the enzyme. This is achieved by the myristic acid having a high enough hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell (Wikipedia). Some research has pointed to myristic acid's positive effects on regulating HDL cholesterol and hence improving the HDL (good cholesterol) to total cholesterol ratio (PMID: 7644455).
CAS Number544-63-8
Structure
Thumb
Synonyms
SynonymSource
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
FEMA 2764db_source
Myristic acidChEBI
Myristic acid, 8CIdb_source
N-Tetradecan-1-oatebiospider
N-Tetradecan-1-oic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.0017 g/LALOGPS
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
Chemical FormulaC14H28O2
IUPAC nametetradecanoic acid
InChI IdentifierInChI=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
Isomeric SMILESCCCCCCCCCCCCCC(O)=O
Average Molecular Weight228.3709
Monoisotopic Molecular Weight228.20893014
Classification
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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 73.63%; H 12.36%; O 14.01%DFC
Melting PointMp 54°DFC
Boiling PointBp16 199°DFC
Experimental Water Solubility0.00107 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP6.11SANGSTER (1993)
Experimental pKa4.9
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-017i-2910000000-66b35fb8449ba9de9cd6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-017i-2910000000-66b35fb8449ba9de9cd6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0159-0910000000-f45703c464ca75f98f26JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9700000000-ec8d81e37bc3b8531c99JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0079-9330000000-5ec01705dfacc992be28JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-0090000000-73ac1cfb8731e6318cc5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004i-1090000000-3aa768974da0ea81c1c9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0090000000-22cd107a87b9acf058c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0090000000-2f7bb32e4b42206d851dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-2090000000-d45cffc15e2efbd45cd6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9200000000-dbca68238dfebab35251JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004r-9000000000-26827be8f8c2a4fbfd75JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0006-0090000000-110165b889d231d09d59JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0006-0090000000-110165b889d231d09d59JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0006-0090000000-110165b889d231d09d59JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0090000000-110165b889d231d09d59JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-91f4f874b25705464fb0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-15225a799e0a0bcff7c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0090000000-fde345db8c562ea351deJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-004i-0090000000-79a1c6b1d8cd57b741d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-22cd107a87b9acf058c5JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-0090000000-2f7bb32e4b42206d851dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-2090000000-d45cffc15e2efbd45cd6JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-001i-9200000000-dbca68238dfebab35251JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004r-9000000000-26827be8f8c2a4fbfd75JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-004i-0090000000-90c0cde444dfbbc0051dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-91f4f874b25705464fb0JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-15225a799e0a0bcff7c7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0090000000-fde345db8c562ea351deJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 10V, positivesplash10-004i-0090000000-b2104d749fc73640de02JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-06xx-9200000000-4fdd41f0461ff5186901JSpectraViewer | MoNA
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
ChemSpider ID10539
ChEMBL IDCHEMBL111077
KEGG Compound IDC06424
Pubchem Compound ID11005
Pubchem Substance IDNot Available
ChEBI ID28875
Phenol-Explorer IDNot Available
DrugBank IDDB08231
HMDB IDHMDB00806
CRC / DFC (Dictionary of Food Compounds) IDCPB50-O:CPB50-O
EAFUS ID2626
Dr. Duke IDN-TETRADECANOIC-ACID|MYRISTIC-ACID|TETRADECANOIC-ACID
BIGG ID215851
KNApSAcK IDC00001228
HET IDMYR
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1009061
SuperScent IDNot Available
Wikipedia IDMyristic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
antioxidant22586 A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
cosmetic64857 The role played by a substance in enhancing the appearance or odour of the human body; a name given to the substance itself or to a component of it.DUKE
hypercholesterolemicDUKE
lubricantDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
Enzymes
NameGene NameUniProt ID
Liver carboxylesterase 1CES1P23141
Pancreatic triacylglycerol lipasePNLIPP16233
Hepatic triacylglycerol lipaseLIPCP11150
Inactive pancreatic lipase-related protein 1PNLIPRP1P54315
Patatin-like phospholipase domain-containing protein 3PNPLA3Q9NST1
Gastric triacylglycerol lipaseLIPFP07098
Endothelial lipaseLIPGQ9Y5X9
Pancreatic lipase-related protein 2PNLIPRP2P54317
Lipoprotein lipaseLPLP06858
Patatin-like phospholipase domain-containing protein 4PNPLA4P41247
Patatin-like phospholipase domain-containing protein 2PNPLA2Q96AD5
Pancreatic lipase-related protein 3PNLIPRP3Q17RR3
CholinesteraseBCHEP06276
Carboxylesterase 5ACES5AQ6NT32
60 kDa lysophospholipaseASPGQ86U10
Dehydrogenase/reductase SDR family member 4DHRS4Q9BTZ2
Fatty acid synthaseFASNP49327
Galactoside-binding soluble lectin 13LGALS13Q9UHV8
Eosinophil lysophospholipaseCLCQ05315
Cocaine esteraseCES2O00748
Acylphosphatase-2ACYP2P14621
Acylphosphatase-1ACYP1P07311
AspartoacylaseASPAP45381
Aspartoacylase-2ACY3Q96HD9
Lysosomal thioesterase PPT2PPT2Q9UMR5
Acid ceramidaseASAH1Q13510
Homeodomain-interacting protein kinase 1HIPK1Q86Z02
Peroxisome proliferator-activated receptor gammaPPARGP37231
Long-chain fatty acid transport protein 6SLC27A6Q9Y2P4
Long-chain fatty acid transport protein 3SLC27A3Q5K4L6
Long-chain fatty acid transport protein 4SLC27A4Q6P1M0
Putative neutral ceramidase CASAH2CP0C7U2
Alkaline ceramidase 2ACER2Q5QJU3
Neutral ceramidaseASAH2Q9NR71
Alkaline ceramidase 1ACER1Q8TDN7
Neuropathy target esterasePNPLA6Q8IY17
Carboxylesterase 3CES3Q6UWW8
S-acyl fatty acid synthase thioesterase, medium chainOLAHQ9NV23
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid BiosynthesisSMP00456 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
waxy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
soapy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
coconut
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.