Showing Compound Ricinoleic acid (FDB012640)

Record Information

Version

1.0

Creation date

2010-04-08 22:10:17 UTC

Update date

2019-11-26 03:07:16 UTC

Primary ID

FDB012640

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Ricinoleic acid

Description

Occurs in castor oil and other oils e.g. grape and ergot (Claviceps purpurea) Ricinoleic acid (12-hydroxy-9-cis-octadecenoic acid) is an unsaturated omega-9 fatty acid that naturally occurs in mature Castor plant (Ricinus communis L., Euphorbiaceae) seeds or in sclerotium of ergot (Claviceps purpurea Tul., Clavicipitaceae). About 90% of the fatty acid content in castor oil is the triglyceride formed from ricinoleic acid. Ricinoleic acid is manufactured for industries by saponification or fractional distillation of hydrolyzed castor oil. The zinc salt is used in personal care products, such as deodorants. Ricinoleic acid is found in fats and oils, fruits, and corn.

CAS Number

141-22-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
12-Hydroxyoleic acid	ChEBI
12-Hydroxyoleate	Generator
Ricinoleate	Generator
(9Z)-(12S)-Hydroxyoctadecenoic acid	HMDB
(9Z)-12-Hydroxy-9-octadecenoic acid	HMDB
(9Z)-12-Hydroxyoctadec-9-enoic acid	HMDB
(9Z,12R)-12-Hydroxyoctadec-9-enoic acid	HMDB
(R)-12-Hydroxy-cis-9-octadecenoic acid	HMDB
12-Hydroxy-(9Z,12R)-9-octadecenoic acid	HMDB
12-Hydroxy-9-octadecenoic acid	HMDB, MeSH
12-Hydroxy-cis-9-octadecenoic acid	HMDB
12-Hydroxy-oleic acid	HMDB
12-Hydroxy-[R-(Z)]-9-octadecenoic acid	HMDB
D-12-Hydroxyoleic acid	HMDB
Flexricin 100	HMDB
L'acide ricinoleique	HMDB
P -10 acid	HMDB
RCL	HMDB
Ricinelaidic acid	HMDB, MeSH
Ricinic acid	HMDB
Ricinolic acid	HMDB
Ricinusoleic acid	HMDB
Riconoleic acid	HMDB
12-Hydroxy-9-octadecenic acid	MeSH, HMDB
12-Hydroxyoctadec-cis-9-enoic acid	MeSH, HMDB
Ricinoleic acid, (R-(e))-isomer	MeSH, HMDB
(9Z)-12-Hydroxyoctadec-9-enoate	Generator
12-D-Hydroxy-9-trans-octadecenoic acid	MeSH
Ricinoleic acid	MeSH
(9Z,12R)-12-hydroxyoctadec-9-enoic acid	biospider
(9Z)-12-hydroxyoctadec-9-enoic acid	biospider
9-Octadecenoic acid, 12-hydroxy-, (9Z,12R)-	biospider
9-Octadecenoic acid, 12-hydroxy-, (Z)-	biospider
9-Octadecenoic acid, 12-hydroxy-, [R-(Z)]-	biospider

Predicted Properties

Property	Value	Source
Water Solubility	0.0025 g/L	ALOGPS
logP	6.14	ALOGPS
logP	5.4	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	89.07 m³·mol⁻¹	ChemAxon
Polarizability	37.85 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C18H34O3

IUPAC name

(9Z)-12-hydroxyoctadec-9-enoic acid

InChI Identifier

InChI=1S/C18H34O3/c1-2-3-4-11-14-17(19)15-12-9-7-5-6-8-10-13-16-18(20)21/h9,12,17,19H,2-8,10-11,13-16H2,1H3,(H,20,21)/b12-9-

InChI Key

WBHHMMIMDMUBKC-XFXZXTDPSA-N

Isomeric SMILES

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

Average Molecular Weight

298.4608

Monoisotopic Molecular Weight

298.250794954

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
Hydroxy fatty acid
Unsaturated fatty acid
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:85639 )
monounsaturated fatty acid (CHEBI:85639 )
hydroxy fatty acid (CHEBI:85639 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Poaceae

Biological location:

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Pharmaceutical industry:

Laxative

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 72.44%; H 11.48%; O 16.08%	DFC
Melting Point	Mp 5.5°	DFC
Boiling Point	Bp10 245°	DFC
Experimental Water Solubility	3.46 mg/mL at 25 oC	SEIDELL,A (1941)
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	[a]26D +7.15 (c, 5 in Me2CO)	DFC
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	n20D 1.4697	DFC

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Ricinoleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-6950000000-bd57542588f0c1f373c9	Spectrum
Predicted GC-MS	Ricinoleic acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00bi-9341100000-50290e07e9579df3d010	Spectrum
Predicted GC-MS	Ricinoleic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0090000000-b7d5b714e0c3125f33e7	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01wr-5390000000-803f620a2725a28437e3	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000f-9410000000-69dc43fc42f33c85490a	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-81b1052b32aa5dea7caa	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004j-1090000000-882e590b68505336b690	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9520000000-d6043d034d45f5c3c900	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-0090000000-73c92bc92640dda69d13	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002b-0190000000-dd9b67fa784fafec469a	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-054o-9350000000-f54f3e16cea0f73fc3c7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0290000000-2e109924cba4f0fc25a6	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qi-7950000000-b0d44074bb01991c64e0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9300000000-5d488b145dc0c6c88b83	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

4446069

ChEMBL ID

Not Available

KEGG Compound ID

C08365

Pubchem Compound ID

5282942

Pubchem Substance ID

Not Available

ChEBI ID

28592

Phenol-Explorer ID

Not Available

DrugBank ID

DB02955

HMDB ID

HMDB34297

CRC / DFC (Dictionary of Food Compounds) ID

CQH85-N:HJM23-Y

EAFUS ID

Not Available

Dr. Duke ID

RICINOLEIC-ACID

BIGG ID

Not Available

KNApSAcK ID

C00001237

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

Ricinoleic_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
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
carcinogenic	50903	A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities.	DUKE
prostaglandigenic			DUKE
secretogogue			DUKE
soap			DUKE
spermicide			DUKE