AFCDB: oleate (FDB031070)

Record Information

Version

1.0

Creation date

2015-05-07 20:56:56 UTC

Update date

2020-09-17 15:42:26 UTC

Primary ID

FDB031070

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

oleate

Description

Oleic acid, also known as oleate, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Oleic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. In chemical terms, oleic acid is classified as a monounsaturated omega-9 fatty acid. It has the formula CH3(CH2)7CH=CH(CH2)7COOH. The term "oleic" means related to, or derived from, oil or olive, the plant oil that is predominantly composed of oleic acid. Oleic acid is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. Fatty acids such as oleic acid occur primarily esters (not as free acids), mostly in the form of triglycerides, which are the greasy materials in many natural oils. Oleic acid is an odorless, colourless oil, although commercial samples may be yellowish. Oleic acid is particularly abundant in plant oils e.g. olive oil (about 80%), almond oil (about 80%) 59–75% of pecan oil, 61% of canola oil, 36–67% of peanut oil, 60% of macadamia oil, 20–80% of sunflower oil, 15–20% of grape seed oil, 40% of sesame oil and 14% of poppyseed oil. Oleic acid is the most abundant fatty acid in human adipose tissue and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is used in the manufacturing of surfactants, soaps, plasticizers and as an emulsifying agent in foods, lotions, cosmetics and pharmaceuticals. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil . Altered levels of oleic acid have been found to be associated with isovaleric acidemia, which is an inborn error of metabolism.

CAS Number

112-80-1

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.00012 g/L	ALOGPS
logP	7.68	ALOGPS
logP	6.78	ChemAxon
logS	-6.4	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	15	ChemAxon
Refractivity	87.4 m³·mol⁻¹	ChemAxon
Polarizability	37.09 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

C18H34O2

IUPAC name

(9Z)-octadec-9-enoic acid

InChI Identifier

InChI=1S/C18H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H,19,20)/b10-9-

InChI Key

ZQPPMHVWECSIRJ-KTKRTIGZSA-N

Isomeric SMILES

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

Average Molecular Weight

282.4614

Monoisotopic Molecular Weight

282.255880332

Classification

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain 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

octadec-9-enoic acid (CHEBI:16196 )
Unsaturated fatty acids (C00712 )
Monounsaturated fatty acids (C00712 )
Unsaturated fatty acids (LMFA01030002 )

Ontology

Ingestion

Source:

Synthetic:

Personal care product

Biological:

Animal

Plant:

Biological location:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Olive oil

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Not Available
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
EI-MS	Mass Spectrum (Electron Ionization)	splash10-052f-9100000000-350dc6d7ac541a3c5b67	2018-05-25	View Spectrum
GC-MS	oleate, 1 TMS, GC-MS Spectrum	splash10-00vi-9500000000-cdb5366d3ece43c3e166	Spectrum
GC-MS	oleate, 1 TMS, GC-MS Spectrum	splash10-00nb-5900000000-fc03835c9c8fddb27970	Spectrum
GC-MS	oleate, non-derivatized, GC-MS Spectrum	splash10-052f-9100000000-7618883a87bd14687fd5	Spectrum
GC-MS	oleate, non-derivatized, GC-MS Spectrum	splash10-00vi-9500000000-cdb5366d3ece43c3e166	Spectrum
GC-MS	oleate, non-derivatized, GC-MS Spectrum	splash10-00nb-5900000000-fc03835c9c8fddb27970	Spectrum
Predicted GC-MS	oleate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0f6x-9640000000-29b5681d79890854ef2b	Spectrum
Predicted GC-MS	oleate, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0fe0-9431000000-1879934642ac672cb401	Spectrum
Predicted GC-MS	oleate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	oleate, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-00ls-4790000000-d753b2905852ca2a8cbd	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0apm-9100000000-8d5c8ecf0c7a7cc3ccf6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-0aou-9000000000-64594906d693e8a08650	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-00l2-4790000000-aefa66e9f83fcb24ead6	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0apm-9100000000-a71c58b95cb65487eeed	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-0aou-9000000000-5889cbe3dd606123df50	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - FAB-EBEB (JMS-HX/HX 110A, JEOL) , Negative	splash10-001i-0090000000-89531b488fbe899c09e6	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (Unknown) , Positive	splash10-052f-9100000000-de078efada08e691dbb8	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-004i-0092000000-b8aabbdc61f9b89ac359	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0090000000-92096c6b229762c5295f	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-001i-0090000000-5fe8495a19b387bf702c	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 30V, Negative	splash10-001i-0090000000-5d40399b1c736b476445	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-001i-0090000000-45785aeb659bd8a09240	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 10V, Negative	splash10-001i-0091000000-3946ac7663105c7c2700	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-001i-0090000000-ce1372cb3b5e84122349	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-001i-0090000000-92096c6b229762c5295f	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00lr-0090000000-755e8d1537818580a2fd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00y0-4690000000-ca39c5846217fe093227	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0596-9830000000-fcb2923d448d11c54559	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-0090000000-e809fd7222cf63431b77	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001r-1090000000-9c340e3d19cbe7013ccd	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9230000000-6e517cda629fcd4df07d	2016-09-12	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, experimental)		Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

Not Available

ChEMBL ID

Not Available

KEGG Compound ID

Not Available

Pubchem Compound ID

Not Available

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

Not Available

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

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

Not Available

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

Flavor	Citations
fat	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0

Files

MSDS

Not Available

References

Synthesis Reference

Not Available

General Reference

Not Available

Content Reference

oleate (FDB031070)

Structure for FDB031070 (oleate)