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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2012-09-11 19:06:11 UTC
Update Date2018-05-20 09:39:56 UTC
HMDB IDHMDB0034297
Secondary Accession Numbers
  • HMDB34297
Metabolite Identification
Common NameRicinoleic acid
DescriptionRicinoleic acid is found in corn. Ricinoleic acid 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
Structure
Thumb
Synonyms
ValueSource
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 acidMeSH
12-Hydroxyoctadec-cis-9-enoic acidMeSH
Ricinoleic acid, (R-(e))-isomerMeSH
Chemical FormulaC18H34O3
Average Molecular Weight298.4608
Monoisotopic Molecular Weight298.250794954
IUPAC Name(9Z)-12-hydroxyoctadec-9-enoic acid
Traditional Name12-hydroxy-oleic acid
CAS Registry Number141-22-0
SMILES
CCCCCCC(O)C\C=C/CCCCCCCC(O)=O
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 KeyWBHHMMIMDMUBKC-XFXZXTDPSA-N
Chemical Taxonomy
DescriptionThis compound 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 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point5.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.46 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
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
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6950000000-bd57542588f0c1f373c9View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00bi-9341100000-50290e07e9579df3d010View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-b7d5b714e0c3125f33e7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01wr-5390000000-803f620a2725a28437e3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000f-9410000000-69dc43fc42f33c85490aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-81b1052b32aa5dea7caaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004j-1090000000-882e590b68505336b690View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9520000000-d6043d034d45f5c3c900View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012640
KNApSAcK IDC00001237
Chemspider ID4446069
KEGG Compound IDC08365
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRicinoleic acid
METLIN IDNot Available
PubChem Compound5282942
PDB IDNot Available
ChEBI ID85639
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Gullikson GW, Sender M, Bass P: Laxative-like effects of nonsteroidal anti-inflammatory drugs on intestinal fluid movement and membrane integrity. J Pharmacol Exp Ther. 1982 Feb;220(2):236-42. [PubMed:6948953 ]
  2. Vieira C, Evangelista S, Cirillo R, Terracciano R, Lippi A, Maggi CA, Manzini S: Antinociceptive activity of ricinoleic acid, a capsaicin-like compound devoid of pungent properties. Eur J Pharmacol. 2000 Oct 27;407(1-2):109-16. [PubMed:11050297 ]
  3. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  4. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  5. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  6. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  7. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  8. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.