ChemFOnt: Showing chemical card for (9E,12Z)-octadeca-9,12-dienoic acid (CFc000154282)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 23:39:03 UTC

Chemfont ID

CFc000154282

Molecule Identification

Common Name

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

Definition

Linoleic acid, also known as LA or cis,cis-linoleate, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Based on a literature review a significant number of articles have been published on Linoleic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(9Z,12Z)-Octadecadienoic acid	ChEBI
(Z,Z)-9,12-Octadecadienoic acid	ChEBI
9-cis,12-cis-Octadecadienoic acid	ChEBI
9Z,12Z-Octadecadienoic acid	ChEBI
Acide cis-linoleique	ChEBI
Acide linoleique	ChEBI
Acido linoleico	ChEBI
all-cis-9,12-Octadecadienoic acid	ChEBI
C18:2 9C, 12C Omega6 todos cis-9,12-octadienoico	ChEBI
C18:2, N-6,9 all-cis	ChEBI
cis,cis-9,12-Octadecadienoic acid	ChEBI
cis,cis-Linoleic acid	ChEBI
cis-Delta(9,12)-Octadecadienoic acid	ChEBI
LA	ChEBI
Linolic acid	ChEBI
9-cis,12-cis-Octadecadienoate	Kegg
(9Z,12Z)-Octadecadienoate	Generator
(Z,Z)-9,12-Octadecadienoate	Generator
9Z,12Z-Octadecadienoate	Generator
all-cis-9,12-Octadecadienoate	Generator
cis,cis-9,12-Octadecadienoate	Generator
cis,cis-Linoleate	Generator
cis-delta(9,12)-Octadecadienoate	Generator
cis-Δ(9,12)-octadecadienoate	Generator
cis-Δ(9,12)-octadecadienoic acid	Generator
Linolate	Generator
Linoleate	Generator
(9Z,12Z)-9,12-Octadecadienoate	HMDB
(9Z,12Z)-9,12-Octadecadienoic acid	HMDB
9-cis,12-cis-Linoleate	HMDB
9-cis,12-cis-Linoleic acid	HMDB
9Z,12Z-Linoleate	HMDB
9Z,12Z-Linoleic acid	HMDB
cis-9,cis-12-Octadecadienoate	HMDB
cis-9,cis-12-Octadecadienoic acid	HMDB
cis-D9,12-Octadecadienoate	HMDB
cis-D9,12-Octadecadienoic acid	HMDB
Emersol 315	HMDB
Extra linoleic 90	HMDB
Polylin 515	HMDB
Unifac 6550	HMDB
Acid, 9,12-octadecadienoic	HMDB
Linoelaidic acid	HMDB
Linoleic acid, (e,e)-isomer	HMDB
Linoleic acid, (Z,Z)-isomer	HMDB
Linoleic acid, (Z,Z)-isomer, 14C-labeled	HMDB
Linoleic acid, ammonium salt, (Z,Z)-isomer	HMDB
Linoleic acid, potassium salt, (Z,Z)-isomer	HMDB
9 trans,12 trans Octadecadienoic acid	HMDB
9-trans,12-trans-Octadecadienoic acid	HMDB
Linoleic acid, sodium salt, (e,e)-isomer	HMDB
Linoleic acid, sodium salt, (Z,Z)-isomer	HMDB
trans,trans-9,12-Octadecadienoic acid	HMDB
9,12-Octadecadienoic acid	HMDB
Linoelaidic acid, (e,Z)-isomer	HMDB
Linoleic acid, calcium salt, (Z,Z)-isomer	HMDB
Linolelaidic acid	HMDB
9,12 Octadecadienoic acid	HMDB
Linoleic acid, (Z,e)-isomer	HMDB
FA(18:2(9Z,12Z))	HMDB

Chemical Formula

C₁₈H₃₂O₂

Average Molecular Weight

280.4455

Monoisotopic Molecular Weight

280.240230268

IUPAC Name

(9Z,12Z)-octadeca-9,12-dienoic acid

Traditional Name

linoleic

CAS Registry Number

60-33-3

SMILES

CCCCC\C=C/C\C=C/CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-

InChI Key

OYHQOLUKZRVURQ-HZJYTTRNSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
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 Framework

Aliphatic acyclic compounds

External Descriptors

omega-6 fatty acid (CHEBI:17351 )
octadecadienoic acid (CHEBI:17351 )
Unsaturated fatty acids (C01595 )
Polyunsaturated fatty acids (C01595 )
Unsaturated fatty acids (LMFA01030120 )

Functional Ontology

Not Available

Not Available

Not Available

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.00015 g/L	ALOGPS
logP	7.06	ALOGPS
logP	6.42	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	88.52 m³·mol⁻¹	ChemAxon
Polarizability	35.86 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon