Linoelaidic acid

PUFA18:2Ω-6 Trans

  Overview

Stats

PUFA
Type
18
Carbons
2
Double bonds
1
Bis-allylic sites
280.4
Weight · g/mol
28.5 °C
Melting point
C18H32O2
Formula

Also known as

IUPAC (9E,12E)-octadeca-9,12-dienoic acid

  At a Glance

Source

Primarily from industrial.

Type

Long-chain polyunsaturated fatty acid with 18 carbons and two trans double bonds, an omega-6 fatty acid.

Identification

  Synonyms

Common Name Linoelaidic acid
IUPAC Name (9E,12E)-octadeca-9,12-dienoic acid
Traditional Name —
Other Synonyms No other synonyms recorded.

  External IDs

General References
Lipids
Lipid Maps LMFA01030123
Lipid Bank DFA0160
Swiss Lipids 000000407
PlantFA ID —
Food & Nutrition
FooDB FDB023868
INFOODS —
Chemistry / Compounds
PubChem CID 5282457
CAS 506-21-8
ChEBI 75108
ChEMBL CHEMBL93204
ChemSpider 4445609
InChIKey —
ZINC ID ZINC000003802188
NIKKAJI ID J294.477D, J12.231I
PDBe —
UCI (UniChem) 186881
SureChEMBL 120856
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB0006270
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID MTBLS1485
BioCyc/MetaCyc —
MetaNetX ID MNXM293
BiGG ID 2217974
KEGG —
KNApSAcK C00036669
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs PD020553
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) 7552P0K6PN
FDA SRS (USA) 7552P0K6PN
NHPID (Canada) —
DTXSID (USA) DTXSID50897508
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort Molport-001-780-227
eMolecules —
Mcule —
ChemicalBook —
MedChemExpress —

Isomers of 18:2 (7)

Other fatty acids sharing the 18:2 notation — differing by double-bond position, geometry (cis/trans), or conjugation.

Name Geometry Trans Structure PubChem
Current Fatty Acid
Linoelaidic acid
(9E,12E)-octadeca-9,12-dienoic acid
 9E,12E Trans
5282457
Category —
Conjugation Type Isolated
SMILES CCCCC\C=C\C/C=C/CCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
Geometric (3)
Linoleic acid
(9Z,12Z)-octadeca-9,12-dienoic acid
 9Z,12Z —
5280450
Category —
Conjugation Type Isolated
SMILES CCCCC\C=C/C\C=C/CCCCCCCC(O)=O
Description —
Origin Details

No origin information recorded.
9Z,12E-Octadecadienoic Acid
(9Z,12E)-octadeca-9,12-dienoic acid
 9Z,12E Trans
Category Isolated mono-trans Fatty Acid
Conjugation Type Isolated
SMILES CCCCC/C=C/C\C=C/CCCCCCCC(=O)O
Description A mono-trans geometric isomer where only the delta-12 double bond has been flipped into the E configuration.
Origin Details
Origin Source Type Details
Thermal/Refining Degradation Cooking Formed during high-temperature industrial deodorization, chemical refining processes, or extended deep-frying of seed oils.
9E,12Z-Octadecadienoic Acid
(9E,12Z)-octadeca-9,12-dienoic acid
 9E,12Z Trans
6442998
Category Isolated mono-trans Fatty Acid
Conjugation Type Isolated
SMILES CCCCC\C=C/C/C=C/CCCCCCCC(=O)O
Description A mono-trans geometric isomer where only the delta-9 double bond has been converted to the E conformation.
Origin Details
Origin Source Type Details
Thermal/Refining Degradation Cooking Generated via free radical-mediated isomerization during the severe thermal stress or commercial processing of plant lipid matrices.
Positional (3)
Rumenic acid
(9Z,11E)-octadeca-9,11-dienoic acid
 9Z,11E Trans
5280644
Category —
Conjugation Type Conjugated
SMILES CCCCCC\C=C\C=C/CCCCCCCC(O)=O
Description —
Origin Details

No origin information recorded.
(10E,12Z)-Octadecadienoic acid
(10E,12Z)-octadeca-10,12-dienoic acid
 10E,12Z Trans
5282800
Category —
Conjugation Type Conjugated
SMILES CCCCC/C=C\C=C\CCCCCCCCC(=O)O
Description —
Origin Details

No origin information recorded.
9E,11E-CLA
(9E,11E)-octadeca-9,11-dienoic acid
 9E,11E Trans
5460677
Category Conjugated trans-trans Fatty Acid
Conjugation Type Conjugated
SMILES CCCCCC/C=C/C=C/CCCCCCCC(=O)O
Description The fully conjugated di-trans isomer, possessing the highest melting point of the 18:2 series due to its straight linear structural stacking capabilities.
Origin Details
Origin Source Type Details
Severe Thermal Conversion Cooking Formed through the rigorous thermal degradation or extreme catalytic processing of standard conjugated linoleic acids.

Chemical Properties

Name(s):
Common Name Linoelaidic acid
Simple Notation 18:2
Notation 18:2(n-6)
IUPAC Name (9E,12E)-octadeca-9,12-dienoic acid
Structure:
Molecular C18H32O2
Structure CH3(CH2)4CH=CHCH2CH=CH(CH2)7COOH
SMILES CCCCC\C=C\C/C=C/CCCCCCCC(=O)O
Cis / Trans trans
E-Z 9E,12E
Physical:
Weight 280.4 g/mol
Melting Point 28.5 °C
Reactivity
Double Bonds 2
Bis-Allylic Carbons 1 (High Reactivity)
Beta-Oxidation
Beta Oxidation Cycles 8
ATP Yield (Net) 117 ATP