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8,11,14-Eicosatrienoic acid (PC000754)

Record Information
Version1.0
Creation date2015-10-09 22:32:32 UTC
Update date2017-01-19 02:36:35 UTC
FoodComEx IDPC000754
FoodDB RecordFDB023082
Chemical Information
Name8,11,14-Eicosatrienoic acid
Description8,11,14-Eicosatrienoic acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 8,11,14-Eicosatrienoic acid is also known as Dihomo-gamma-linolenic acid (DGLA). In physiological literature, it is given the name 20:3(n-6). DGLA is the elongation product of the 18 carbon gamma-linolenic acid (GLA). DGLA can be converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect. DGLA competes with arachadonic acid for COX and lipoxygenase, inhibiting the production of arachadonic acid's eicosanoids [HMDB]
CAS Number1783-84-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
(8Z,11Z,14Z)-Icosatrienoatehmdb
(8Z,11Z,14Z)-Icosatrienoic acidhmdb
(Z,Z,Z)-8,11,14-Eicosatrienoatehmdb
(Z,Z,Z)-8,11,14-Eicosatrienoic acidhmdb
(Z,Z,Z)-8,11,14-Icosatrienoatehmdb
(Z,Z,Z)-8,11,14-Icosatrienoic acidhmdb
(Z,Z,Z)-icosatri-8,11,14-enoatehmdb
(Z,Z,Z)-icosatri-8,11,14-enoic acidhmdb
20:3, N-6,9,12 all-cisChEBI
8,11,14-all-cis-Eicosatrienoatehmdb
8,11,14-all-cis-Eicosatrienoic acidhmdb
8,11,14-Eicosatrienoatehmdb
8,11,14-Eicosatrienoic acidhmdb
8,11,14-Icosatrienoatehmdb
8,11,14-Icosatrienoic acidhmdb
8c,11c,14c-EicosatrienoateGenerator
8c,11c,14c-Eicosatrienoic acidChEBI
8c,11c,14c-EicosatriensaeureChEBI
8Z,11Z,14Z-eicosatrienoatehmdb
8Z,11Z,14Z-eicosatrienoic acidhmdb
all-cis-8,11,14-Eicosatrienoatehmdb
all-cis-8,11,14-Eicosatrienoic acidhmdb
all-cis-8,11,14-IcosatrienoateGenerator
all-cis-8,11,14-Icosatrienoic acidChEBI
all-cis-Eicosa-8,11,14-trienoateGenerator
all-cis-Eicosa-8,11,14-trienoic acidChEBI
all-cis-Eicosa-8,11,14-triensaeureChEBI
Bishomo-gamma-linolenatehmdb
Bishomo-gamma-linolenic acidhmdb
C20:3, N-6,9,12 all-cisChEBI
cis-8,11,14-Eicosatrienoatehmdb
cis-8,11,14-Eicosatrienoic acidhmdb
cis-8,cis-11,cis-14-Eicosatrienoatehmdb
cis-8,cis-11,cis-14-Eicosatrienoic acidhmdb
cis,cis,cis-8,11,14-Eicosatrienoatehmdb
cis,cis,cis-8,11,14-Eicosatrienoic acidhmdb
DGLAhmdb
Dihomo-g-linolenateGenerator
Dihomo-g-linolenic acidGenerator
Dihomo-gamma-linolenatehmdb
Dihomo-gamma-linolenic acidhmdb
Dihomo-γ-linolenateGenerator
Dihomo-γ-linolenic acidGenerator
Eicosa-8Z,11Z,14Z-trienoateGenerator
Eicosa-8Z,11Z,14Z-trienoic acidChEBI
Eicosatrienoatehmdb
Eicosatrienoic acidhmdb
g-HomolinolenateGenerator
g-Homolinolenic acidGenerator
gamma-Homolinolenatehmdb
gamma-Homolinolenic acidhmdb
Homo-g-linolenateGenerator
Homo-g-linolenic acidGenerator
Homo-g-linolensaeureGenerator
Homo-gamma-linolenatehmdb
Homo-gamma-linolenic acidChEBI
Homo-gamma-linolensaeureChEBI
Homo-γ-linolenateGenerator
Homo-γ-linolenic acidGenerator
Homo-γ-linolensaeureGenerator
γ-homolinolenateGenerator
γ-homolinolenic acidGenerator
Chemical FormulaC20H34O2
IUPAC nameicosa-8,11,14-trienoic acid
InChI IdentifierInChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)
InChI KeyHOBAELRKJCKHQD-UHFFFAOYSA-N
Isomeric SMILESCCCCCC=CCC=CCC=CCCCCCCC(O)=O
Average Molecular Weight306.4828
Monoisotopic Molecular Weight306.255880332
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
  • 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 DescriptorsNot Available
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 10 mg
Delivery TimeNot Available
Storage Formliquid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci Y1802
Cayman Chemical 90230
MetaSci HMDB0002925
Toronto Research Chemicals E477930
Toronto Research Chemicals HMDB0002925