Record Information
Version1.0
Creation date2010-04-08 22:10:17 UTC
Update date2019-11-26 03:07:16 UTC
Primary IDFDB012640
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameRicinoleic acid
DescriptionOccurs 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 Number141-22-0
Structure
Thumb
Synonyms
SynonymSource
12-Hydroxyoleic acidChEBI
12-HydroxyoleateGenerator
RicinoleateGenerator
(9Z)-(12S)-Hydroxyoctadecenoic acidHMDB
(9Z)-12-Hydroxy-9-octadecenoic acidHMDB
(9Z)-12-Hydroxyoctadec-9-enoic acidHMDB
(9Z,12R)-12-Hydroxyoctadec-9-enoic acidHMDB
(R)-12-Hydroxy-cis-9-octadecenoic acidHMDB
12-Hydroxy-(9Z,12R)-9-octadecenoic acidHMDB
12-Hydroxy-9-octadecenoic acidHMDB
12-Hydroxy-cis-9-octadecenoic acidHMDB
12-Hydroxy-oleic acidHMDB
12-Hydroxy-[R-(Z)]-9-octadecenoic acidHMDB
D-12-Hydroxyoleic acidHMDB
Flexricin 100HMDB
L'acide ricinoleiqueHMDB
p -10 acidHMDB
RCLHMDB
Ricinelaidic acidHMDB
Ricinic acidHMDB
Ricinolic acidHMDB
Ricinusoleic acidHMDB
Riconoleic acidHMDB
12-Hydroxy-9-octadecenic acidHMDB
12-Hydroxyoctadec-cis-9-enoic acidHMDB
Ricinoleic acid, (R-(e))-isomerHMDB
12-D-Hydroxy-9-trans-octadecenoic acidMeSH
(9Z)-12-Hydroxyoctadec-9-enoateGenerator
Ricinoleic acidMeSH
(9Z,12R)-12-hydroxyoctadec-9-enoic acidbiospider
(9Z)-12-hydroxyoctadec-9-enoic acidbiospider
9-Octadecenoic acid, 12-hydroxy-, (9Z,12R)-biospider
9-Octadecenoic acid, 12-hydroxy-, (Z)-biospider
9-Octadecenoic acid, 12-hydroxy-, [R-(Z)]-biospider
P -10 acidHMDB
Predicted Properties
PropertyValueSource
Water Solubility0.0025 g/LALOGPS
logP6.14ALOGPS
logP5.4ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity89.07 m³·mol⁻¹ChemAxon
Polarizability37.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC18H34O3
IUPAC name(9Z)-12-hydroxyoctadec-9-enoic acid
InChI IdentifierInChI=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 KeyWBHHMMIMDMUBKC-XFXZXTDPSA-N
Isomeric SMILESCCCCCCC(O)C\C=C/CCCCCCCC(O)=O
Average Molecular Weight298.4608
Monoisotopic Molecular Weight298.250794954
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative ParentsNot Available
SubstituentsNot Available
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 72.44%; H 11.48%; O 16.08%DFC
Melting PointMp 5.5°DFC
Boiling PointBp10 245°DFC
Experimental Water Solubility3.46 mg/mL at 25 oCSEIDELL,A (1941)
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]26D +7.15 (c, 5 in Me2CO)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.4697DFC
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6950000000-bd57542588f0c1f373c9JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00bi-9341100000-50290e07e9579df3d010JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-b7d5b714e0c3125f33e7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01wr-5390000000-803f620a2725a28437e3JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9410000000-69dc43fc42f33c85490aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-81b1052b32aa5dea7caaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-1090000000-882e590b68505336b690JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9520000000-d6043d034d45f5c3c900JSpectraViewer
ChemSpider ID4446069
ChEMBL IDNot Available
KEGG Compound IDC08365
Pubchem Compound ID5282942
Pubchem Substance IDNot Available
ChEBI ID28592
Phenol-Explorer IDNot Available
DrugBank IDDB02955
HMDB IDHMDB34297
CRC / DFC (Dictionary of Food Compounds) IDCQH85-N:HJM23-Y
EAFUS IDNot Available
Dr. Duke IDRICINOLEIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001237
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDRicinoleic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti leukotriene-D435222 A substance that diminishes the rate of a chemical reaction.DUKE
carcinogenic50903 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
prostaglandigenicDUKE
secretogogueDUKE
soapDUKE
spermicideDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).