AFCDB: Oleic acid (FDB012858)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:24 UTC

Update date

2019-11-26 03:07:45 UTC

Primary ID

FDB012858

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Oleic acid

Description

Major constituent of plant oils e.g. olive oil (ca. 80%), almond oil (ca. 80%) and many others, mainly as glyceride. Constituent of tall oiland is also present in apple, melon, raspberry oil, tomato, banana, roasted peanuts, black tea, rice bran, cardamon, plum brandy, peated malt, dairy products and various animal fats. Component of citrus fruit coatings. Emulsifying agent in foods Oleic acid is a monounsaturated omega-9 fatty acid found in various animal and vegetable fats. The trans isomer of oleic acid is called elaidic acid.

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-MDZDMXLPSA-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

No ontology term

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 76.54%; H 12.13%; O 11.33%	DFC
Melting Point	Mp 16° (stable form)	DFC
Boiling Point	Bp5 203-205°	DFC
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	d204 0.9	DFC
Refractive Index	n20D 1.4595	DFC

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

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

HMDB00207

CRC / DFC (Dictionary of Food Compounds) ID

BGT64-L:HMN62-J

EAFUS ID

2802

Dr. Duke ID

OLEIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00001232

HET ID

OLA

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

112-80-1

GoodScent ID

rw1029521

SuperScent ID

Not Available

Wikipedia ID

Oleic_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

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
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
alpha-reductase inhibitor	23924	A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.	DUKE
anemiagenic			DUKE
anti alopecic	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 inflammatory	35472	A substance that reduces or suppresses inflammation.	DUKE
anti leukotriene-D4	35222	A substance that diminishes the rate of a chemical reaction.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
choleretic			DUKE
dermatitigenic			DUKE
flavor	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
hypocholesterolemic			DUKE
insectifuge	24852	Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.	DUKE
irritant			DUKE
percutaneostimulant			DUKE
perfumery	48318	A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.	DUKE
propecic			DUKE

Enzymes

Name	Gene Name	UniProt ID
Bile acid-CoA:amino acid N-acyltransferase	BAAT	Q14032
2-acylglycerol O-acyltransferase 2	MOGAT2	Q3SYC2
Fatty-acid amide hydrolase 1	FAAH	O00519
Fatty-acid amide hydrolase 2	FAAH2	Q6GMR7
Fatty acid synthase	FASN	P49327
S-acyl fatty acid synthase thioesterase, medium chain	OLAH	Q9NV23
Cytosolic acyl coenzyme A thioester hydrolase	ACOT7	O00154
Acyl-coenzyme A thioesterase 2, mitochondrial	ACOT2	P49753
Acyl-coenzyme A thioesterase 4	ACOT4	Q8N9L9
Acyl-coenzyme A thioesterase 8	ACOT8	O14734
Acyl-coenzyme A thioesterase 1	ACOT1	Q86TX2

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

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).
— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.

Oleic acid (FDB012858)

Structure for FDB012858 (Oleic acid)