Showing Compound Linoelaidic acid (FDB023868)

Record Information

Version

1.0

Creation date

2011-09-21 00:36:02 UTC

Update date

2019-11-26 03:21:10 UTC

Primary ID

FDB023868

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Linoelaidic acid

Description

Linoelaidic acid is an isomer of linoleic acid, or conjugated linoleic acid (CLA), a derivative of a fatty acid linoleic acid. Conjugated linoleic acid (CLA) isomers, a group of positional and geometric isomers of linoleic acid [18:2(n-6)], have been studied extensively due to their ability to modulate cancer, atherosclerosis, obesity, immune function and diabetes in a variety of experimental models. CLA's ability to modulate human obesity remains controversial because data from clinical trials using mixed isomers are conflicting. (PMID 10759137) Trans fatty acids are characteristically produced during industrial hydrogenation of plant oils. [HMDB]. Linoelaidic acid is found in green zucchini, green bell pepper, and red bell pepper.

CAS Number

506-21-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
18:2, N-6,9 all-trans	ChEBI
9E,12E-Octadecadienoic acid	ChEBI
C18:2, N-6,9 all-trans	ChEBI
trans-9,trans-12-Linoleic acid	ChEBI
9E,12E-Octadecadienoate	Generator
trans-9,trans-12-Linoleate	Generator
Linoelaidate	Generator
(9E,12E)-9,12-Octadecadienoate	HMDB
(9E,12E)-9,12-Octadecadienoic acid	HMDB
9,12-Octadecadienoic acid	MeSH, HMDB
Linoleic acid	MeSH, HMDB
Linoleic acid, (Z,Z)-isomer, 14C-labeled	MeSH, HMDB
Linolelaidic acid	MeSH, HMDB
cis,cis-9,12-Octadecadienoic acid	MeSH, HMDB
Linoleic acid, (e,e)-isomer	MeSH, HMDB
Linoleic acid, (Z,Z)-isomer	MeSH, HMDB
Linoleic acid, ammonium salt, (Z,Z)-isomer	MeSH, HMDB
Linoleic acid, potassium salt, (Z,Z)-isomer	MeSH, HMDB
Linoelaidic acid, (e,Z)-isomer	MeSH, HMDB
9 trans,12 trans Octadecadienoic acid	MeSH, HMDB
Linoleic acid, sodium salt, (e,e)-isomer	MeSH, HMDB
Linoleic acid, sodium salt, (Z,Z)-isomer	MeSH, HMDB
Acid, 9,12-octadecadienoic	MeSH, HMDB
trans,trans-9,12-Octadecadienoic acid	MeSH, HMDB
Linoleic acid, (Z,e)-isomer	MeSH, HMDB
9,12 Octadecadienoic acid	MeSH, HMDB
Linoleic acid, calcium salt, (Z,Z)-isomer	MeSH, HMDB
9-trans,12-trans-Octadecadienoic acid	MeSH, HMDB
Linoleate	MeSH, HMDB, Generator
9E,12E-octadecadienoate	hmdb
9E,12E-octadecadienoic acid	hmdb

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	35.45 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

Chemical Formula

C18H32O2

IUPAC name

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

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-AVQMFFATSA-N

Isomeric SMILES

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

Average Molecular Weight

280.4455

Monoisotopic Molecular Weight

280.240230268

Classification

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:75108 )
octadecadienoic acid (CHEBI:75108 )
Unsaturated fatty acids (LMFA01030123 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Cucurbitaceae

Biological location:

Biofluid and excreta:

Subcellular:

Cell and elements:

Extracellular

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Boiling Point	Not Available
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Linoelaidic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0007-9750000000-50d69948d56dd2ba6e42	Spectrum
Predicted GC-MS	Linoelaidic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0079-9631000000-cc93c24bbf14d81ae9b6	Spectrum
Predicted GC-MS	Linoelaidic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-0udi-0009000000-4dd23c77f8e48c0ab9ec	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0udi-0009000000-4dd23c77f8e48c0ab9ec	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0090000000-dd6cf3859995c0ba8be8	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0090000000-fdabfebc98e900a3a52b	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0091000000-d8e32f26b102cfd39457	Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0090000000-e1aa5a6fc5d53c0d0cb6	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-dd6cf3859995c0ba8be8	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-fdabfebc98e900a3a52b	Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-004i-0090000000-e1aa5a6fc5d53c0d0cb6	Spectrum
MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-004i-0090000000-fdabfebc98e900a3a52b	Spectrum
MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-004i-0090000000-dd6cf3859995c0ba8be8	Spectrum
MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-004i-0090000000-e1aa5a6fc5d53c0d0cb6	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01q9-0190000000-76fe39ad6bbee3f769e7	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0239-5690000000-9af1d7ecbc9ccf182d61	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-006x-8930000000-0032f23abecb3b362ff2	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-b26f2ec0d32875acf897	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004r-1090000000-08e28514e79444592bb5	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9230000000-d3f27ea65196f222f6cd	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-03fd7d53d39127d02766	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01t9-1090000000-e5b6404e73269d5a2528	Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9210000000-da81d6d1d7b1e626e905	Spectrum

NMR

Not Available

External Links

ChemSpider ID

4445609

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

5282457

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB06270

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

2217974

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Linoelaidic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Not Available

Files

MSDS

show

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).

Showing Compound Linoelaidic acid (FDB023868)

Structure for FDB023868 (Linoelaidic acid)