Record Information
Version1.0
Creation date2010-04-08 22:10:16 UTC
Update date2018-01-23 19:24:16 UTC
Primary IDFDB012633
Secondary Accession Numbers
  • FDB006482
Chemical Information
FooDB NameMyristoleic acid
DescriptionOccurs in natural fats, e.g. Cottonseed oil Myristoleic acid is a monounsaturated fatty acid that represent approximately 0.3 - 0.7% of the total fatty acid composition of adipose tissue triacylglycerol in human. (PMID 10393134); It has been suggested that his cytotoxic and effective cell death inducer activity could be used for the treatment of prostate cancer. (PMID 11304730); Myristoleic acid, or 9-tetradecenoic acid, is an omega-5 fatty acid. It is biosynthesized from myristic acid by the enzyme delta-9 desaturase, but it is uncommon in nature. One of the major sources of this fatty acid is the seed oil from plants of the genus Myristicaceae, comprising up to 30 per cent of the oil in some species. Myristoleic acid is found in many foods, some of which are garfish, wheat, soup, and ginger.
CAS Number544-64-9
Structure
Thumb
Synonyms
SynonymSource
(9Z)-Tetradecenoic acidChEBI
(Z)-Tetradec-9-enoic acidChEBI
9-Tetradecenoic acidChEBI
9Z-Tetradecenoic acidChEBI
cis-9-Tetradecenoic acidChEBI
cis-Delta(9)-Tetradecenoic acidChEBI
cis-Tetradec-9-enoic acidChEBI
(9Z)-TetradecenoateGenerator
(Z)-Tetradec-9-enoateGenerator
9-TetradecenoateGenerator
9Z-TetradecenoateGenerator
cis-9-TetradecenoateGenerator
cis-delta(9)-TetradecenoateGenerator
cis-Δ(9)-tetradecenoateGenerator
cis-Δ(9)-tetradecenoic acidGenerator
cis-Tetradec-9-enoateGenerator
MyristoleateGenerator
(9Z)-Tetradec-9-enoateHMDB
(9Z)-Tetradec-9-enoic acidHMDB
(9Z)-9-Tetradecenoic acidbiospider
(9Z)-tetradec-9-enoatebiospider
(9Z)-tetradec-9-enoic acidbiospider
9-Tetradecenoic acid, (9Z)-biospider
9-Tetradecenoic acid, (Z)-biospider
9Z-tetradecenoatebiospider
9Z-tetradecenoic acidbiospider
cis-9-tetradecenoatebiospider
cis-9-tetradecenoic acidbiospider
cis-Delta(9)-tetradecenoatebiospider
cis-Delta(9)-tetradecenoic acidbiospider
cis-δ(9)-tetradecenoateGenerator
cis-δ(9)-tetradecenoic acidGenerator
Myristoleic aciddb_source
Z-9-Tetradecenoic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility0.0022 g/LALOGPS
logP5.69ALOGPS
logP5.01ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity69 m³·mol⁻¹ChemAxon
Polarizability28.75 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC14H26O2
IUPAC name(9Z)-tetradec-9-enoic acid
InChI IdentifierInChI=1S/C14H26O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h5-6H,2-4,7-13H2,1H3,(H,15,16)/b6-5-
InChI KeyYWWVWXASSLXJHU-WAYWQWQTSA-N
Isomeric SMILESCCCC\C=C/CCCCCCCC(O)=O
Average Molecular Weight226.355
Monoisotopic Molecular Weight226.193280076
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
  • Unsaturated 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 74.29%; H 11.58%; O 14.14%DFC
Melting PointMp -4.5°DFC
Boiling PointBp0.03 133°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider ID4444564
ChEMBL IDCHEMBL456732
KEGG Compound IDC08322
Pubchem Compound ID5281119
Pubchem Substance IDNot Available
ChEBI ID27781
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02000
CRC / DFC (Dictionary of Food Compounds) IDCPB82-Z:HJL78-N
EAFUS IDNot Available
Dr. Duke IDMYRISTOLEIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001229
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMyristoleic 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
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
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).
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).