AFCDB: (Z,Z)-9,12-Octadecadienoic acid (FDB012760)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:21 UTC

Update date

2019-11-26 03:07:33 UTC

Primary ID

FDB012760

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

(Z,Z)-9,12-Octadecadienoic acid

Description

Constituent of most vegetable oils and animal fats. The Fe salt is the major component of metallic drier compositions used to line food cans Linoleic acid is one of two essential fatty acids that humans and other animals must ingest for good health, because the body requires them for various biological processes, but cannot synthesize them from other food components. (Z,Z)-9,12-Octadecadienoic acid is found in many foods, some of which are green bean, cloves, kumquat, and pecan nut.

CAS Number

60-33-3

Structure

MOL SDF PDB SMILES InChI

Synonyms

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	35.41 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,12Z)-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-IXWMQOLASA-N

Isomeric SMILES

[H]\C(CCCCC)=C(/[H])C\C([H])=C(/[H])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

Unsaturated fatty acids (LMFA01030122 )

Ontology

No ontology term

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Show entries

Search:

Property	Value	Reference
Boiling Point	Bp0.02 129°	DFC
Charge	Not Available
Density	d254 0.9	DFC
Experimental logP	7.05	SANGSTER (1993)
Experimental pKa	4.77
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 77.09%; H 11.50%; O 11.41%	DFC
Melting Point	Mp -5°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	(Z,Z)-9,12-Octadecadienoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0007-8950000000-f63c2f7a4fb796f5b2d7	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0090000000-8bdf8d54a29f73494242	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0239-4590000000-fc68aa6b94e255713775	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00rf-9830000000-8617b3536d6af2a7f35f	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0090000000-f1e9e4b543f7d4f48bf8	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ti-0090000000-665523c6142ff4e39c96	2018-04-06	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9240000000-dca36a25ad7519d500c3	2018-04-06	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB00673

CRC / DFC (Dictionary of Food Compounds) ID

HDX10-F:HKR32-G

EAFUS ID

2056

Dr. Duke ID

LINOLEIC-ACID|OCTADECA-9,12-DIENOIC-ACID

BIGG ID

37956

KNApSAcK ID

Not Available

HET ID

EIC

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

rw1045901

SuperScent ID

Not Available

Wikipedia ID

Linoleic acid

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

Show entries

Search:

Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Show entries

Search:

Descriptor	ID	Definition	Reference
5alpha-reductase inhibitor	50781	An EC 1.3.1.* (oxidoreductase acting on CH-CH group of donor, NAD(+) or NADP(+) as acceptor) inhibitor that interferes with the action of of 3-oxo-5alpha-steroid 4-dehydrogenase (NADP(+)), EC 1.3.1.22, the enzyme which converts testosterone (CHEBI:17347) into the more potent androgen 5alpha-dihydrotestosterone.	DUKE
anti acne	50177	A drug used to treat or prevent skin disorders or for the routine care of skin.	DUKE
anti alopecic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti anaphylactic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti androgenic	35497	A compound which inhibits or antagonises the biosynthesis or actions of androgens.	DUKE
anti arteriosclerotic	38070	A drug used for the treatment or prevention of cardiac arrhythmias. Anti-arrhythmia drugs may affect the polarisation-repolarisation phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibres.	DUKE
anti arthritic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti coronary	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti eczemic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti fibrinolytic			DUKE

Showing 1 to 10 of 27 entries

Enzymes

Show entries

Search:

Name	Gene Name	UniProt ID
Acyl-coenzyme A thioesterase 1	ACOT1	Q86TX2
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	P49753
Acyl-coenzyme A thioesterase 4	ACOT4	Q8N9L9
Acyl-coenzyme A thioesterase 8	ACOT8	O14734
Bile acid-CoA:amino acid N-acyltransferase	BAAT	Q14032
Cytochrome P450 2D6	CYP2D6	Q6NWU0
Cytochrome P450, family 1, subfamily A, polypeptide 1	CYP1A1	A0N0X8
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	O00154

Showing 1 to 8 of 8 entries

Pathways

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

Show entries

Search:

Flavor	Citations
faint	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
fatty	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.

Showing 1 to 2 of 2 entries

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).
— U.S. Department of Agriculture, Agricultural Research Service. 2008. USDA National Nutrient Database for Standard Reference, Release 21. Nutrient Data Laboratory Home Page.
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).

(Z,Z)-9,12-Octadecadienoic acid (FDB012760)

Structure for FDB012760 ((Z,Z)-9,12-Octadecadienoic acid)