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Showing Compound Tetradecanoic acid (FDB002890)

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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-06xx-9200000000-4fdd41f0461ff51869012014-09-20View Spectrum
GC-MSTetradecanoic acid, 1 TMS, GC-MS Spectrumsplash10-017i-2910000000-66b35fb8449ba9de9cd6Spectrum
GC-MSTetradecanoic acid, non-derivatized, GC-MS Spectrumsplash10-017i-2910000000-66b35fb8449ba9de9cd6Spectrum
GC-MSTetradecanoic acid, non-derivatized, GC-MS Spectrumsplash10-0159-0910000000-f45703c464ca75f98f26Spectrum
Predicted GC-MSTetradecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9700000000-ec8d81e37bc3b8531c99Spectrum
Predicted GC-MSTetradecanoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0079-9330000000-5ec01705dfacc992be28Spectrum
Predicted GC-MSTetradecanoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTetradecanoic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-004i-0090000000-73ac1cfb8731e6318cc52012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-004i-1090000000-3aa768974da0ea81c1c92012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-004i-0090000000-22cd107a87b9acf058c52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-0090000000-2f7bb32e4b42206d851d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-2090000000-d45cffc15e2efbd45cd62012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-001i-9200000000-dbca68238dfebab352512012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004r-9000000000-26827be8f8c2a4fbfd752012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0006-0090000000-110165b889d231d09d592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0006-0090000000-110165b889d231d09d592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0006-0090000000-110165b889d231d09d592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0090000000-110165b889d231d09d592017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0090000000-91f4f874b25705464fb02017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0090000000-15225a799e0a0bcff7c72017-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0290000000-b88426a2003ceec57e302015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-5940000000-6c73dc0032502abe4fc42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-bde9bfcd2889066fc8532015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0290000000-b88426a2003ceec57e302015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-5940000000-6c73dc0032502abe4fc42015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9300000000-bde9bfcd2889066fc8532015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-a32f141c7b5af0bc4de12015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1490000000-14bfb0d0344d7cf634432015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-512abb1322963024336f2015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0190000000-a32f141c7b5af0bc4de12015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-057i-1490000000-14bfb0d0344d7cf634432015-05-27View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9400000000-512abb1322963024336f2015-05-27View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, CDCl3, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Spectrum
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
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
Enzymes
Pathways
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
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.