(10E,12Z)-Octadecadienoic acidt10,c12-CLA

PUFA18:2Ω-6 Trans CLA

  Overview

Stats

PUFA
Type
18
Carbons
2
Double bonds
0
Bis-allylic sites
280.4
Weight · g/mol
—
Melting point
C18H32O2
Formula

Also known as

IUPAC (10E,12Z)-octadeca-10,12-dienoic acid
Synonyms

  At a Glance

Source

Primarily from industrial; also in ruminant fat.

Type

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

Identification

  Synonyms

Common Name (10E,12Z)-Octadecadienoic acid
IUPAC Name (10E,12Z)-octadeca-10,12-dienoic acid
Traditional Name —
Other Synonyms
  • 10-trans,12-cis-CLA

  External IDs

General References
Wikipedia —
Lipids
Lipid Maps LMFA01030125
Lipid Bank DFA0164
Swiss Lipids —
PlantFA ID —
Food & Nutrition
FooDB —
INFOODS —
Chemistry / Compounds
PubChem CID 5282800
CAS 2420-44-2
ChEBI 44526
ChEMBL —
ChemSpider —
InChIKey —
ZINC ID —
NIKKAJI ID —
PDBe —
UCI (UniChem) 13205096
SureChEMBL —
CCDC —
NMRShiftDB —
Metabolites & Pathways
HMDB HMDB05048
METLIN —
RefMet ID —
RefMet Name —
MetaboLights ID —
BioCyc/MetaCyc —
MetaNetX ID —
BiGG ID —
KEGG —
KNApSAcK —
Reactome ID —
Drugs & Pharmacology
DrugBank —
DrugCentral —
BindingDB —
Guide to Pharm —
Probes & Drugs —
Clinical & Medical
SNOMED-CT —
MeSH —
NCIt Code —
Regulatory
NIH UNII (USA) —
FDA SRS (USA) —
NHPID (Canada) —
DTXSID (USA) —
TGA Ing ID (Australia) —
Commercial Suppliers
MolPort —
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
(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.
Positional (6)
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.
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.
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.
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.
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 (10E,12Z)-Octadecadienoic acid
Abbreviation t10,c12-CLA
Simple Notation 18:2
Notation 18:2(n-6) conjugated 10t,12c
IUPAC Name (10E,12Z)-octadeca-10,12-dienoic acid
Structure:
Molecular C18H32O2
SMILES CCCCC/C=C\C=C\CCCCCCCCC(=O)O
Cis / Trans trans
E-Z 10E,12Z
Physical:
Weight 280.4 g/mol
Reactivity
Double Bonds 2
Bis-Allylic Carbons 0
Beta-Oxidation
Beta Oxidation Cycles 8
ATP Yield (Net) 117 ATP