Triricinolein (CHEM031465)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 02:40:21 UTC
Update Date2016-11-09 01:19:16 UTC
Accession NumberCHEM031465
Identification
Common NameTriricinolein
ClassSmall Molecule
DescriptionTriricinolein is found in fats and oils. Triricinolein is isolated from castor oil (Ricinus communis).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2,3-Propanetriol tri(12-hydroxy-9-octadecenoate)HMDB
12-Hydroxy-9-octadecenoic acid, 1,2,3-propanetriyl esterHMDB
9-Octadecenoic acid, 12-hydroxy-, 1,2,3-propanetriyl esterHMDB
Glycerol triricinoleateHMDB
Glyceryl triricinoleateHMDB
RicinoleinHMDB
Tri-ricinoleinHMDB
2-{[(9E)-12-hydroxyoctadec-9-enoyl]oxy}-3-{[(9Z)-12-hydroxyoctadec-9-enoyl]oxy}propyl (9Z)-12-hydroxyoctadec-9-enoic acidGenerator
Chemical FormulaC57H104O9
Average Molecular Mass933.430 g/mol
Monoisotopic Mass932.768 g/mol
CAS Registry Number2540-54-7
IUPAC Name2-{[(9E)-12-hydroxyoctadec-9-enoyl]oxy}-3-{[(9Z)-12-hydroxyoctadec-9-enoyl]oxy}propyl (9Z)-12-hydroxyoctadec-9-enoate
Traditional Name2-{[(9E)-12-hydroxyoctadec-9-enoyl]oxy}-3-{[(9Z)-12-hydroxyoctadec-9-enoyl]oxy}propyl (9Z)-12-hydroxyoctadec-9-enoate
SMILESCCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C/CC(O)CCCCCC)OC(=O)CCCCCCC\C=C\CC(O)CCCCCC
InChI IdentifierInChI=1S/C57H104O9/c1-4-7-10-31-40-51(58)43-34-25-19-13-16-22-28-37-46-55(61)64-49-54(66-57(63)48-39-30-24-18-15-21-27-36-45-53(60)42-33-12-9-6-3)50-65-56(62)47-38-29-23-17-14-20-26-35-44-52(59)41-32-11-8-5-2/h25-27,34-36,51-54,58-60H,4-24,28-33,37-50H2,1-3H3/b34-25-,35-26-,36-27+
InChI KeyZEMPKEQAKRGZGQ-YAFIDQONSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassGlycerolipids
Sub ClassTriradylcglycerols
Direct ParentTriacylglycerols
Alternative Parents
Substituents
  • Triacyl-sn-glycerol
  • Tricarboxylic acid or derivatives
  • Fatty alcohol
  • Fatty acid ester
  • Fatty acyl
  • Secondary alcohol
  • Carboxylic acid ester
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.6e-05 g/LALOGPS
logP9.54ALOGPS
logP16.35ChemAxon
logS-7.4ALOGPS
pKa (Strongest Acidic)18.4ChemAxon
pKa (Strongest Basic)-0.83ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area139.59 ŲChemAxon
Rotatable Bond Count53ChemAxon
Refractivity277.25 m³·mol⁻¹ChemAxon
Polarizability121.04 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-35430091881df10d355fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000009-35430091881df10d355fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-0000009007-f3a695322ab20fc7ae65Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0000000009-1036e4d459cbe7999dafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0000000009-1036e4d459cbe7999dafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-0000000009-1036e4d459cbe7999dafSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0000001096-1a82354c75ad069c55e6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0100000192-6ec621764fdc4c313168Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbj-1120008950-acbe512595b8978efd8bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-01q9-0030006019-1dfb61d3f0f4d8b69dacSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-02ea-0096008324-c84a42cc5b4114ac7af2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-1095008000-c3e719e29fb33cd3225cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0000000009-dab299a260c09517b4cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0000000009-dab299a260c09517b4cdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0019-0010009007-b0ad1296ee0d66d15b8eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0000000009-b214f3614079fb6bcb00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0000000009-b214f3614079fb6bcb00Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a56-0009009009-d454d9ec18c34b630c58Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0038061
FooDB IDFDB017272
Phenol Explorer IDNot Available
KNApSAcK IDC00057288
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkRicinolein
Chemspider ID35014503
ChEBI IDNot Available
PubChem Compound ID131752288
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Lin JT, Arcinas A, Harden LR, Fagerquist CK: Identification of (12-ricinoleoylricinoleoyl)diricinoleoylglycerol, an acylglycerol containing four acyl chains, in castor (Ricinus communis L.) oil by LC-ESI-MS. J Agric Food Chem. 2006 May 17;54(10):3498-504.
2. Watson WC, Murray ES: Triricinolein synthesis in vivo. Biochim Biophys Acta. 1965 Oct 4;106(2):311-4.
3. Lin JT, Woodruff CL, Lagouche OJ, McKeon TA, Stafford AE, Goodrich-Tanrikulu M, Singleton JA, Haney CA: Biosynthesis of triacylglycerols containing ricinoleate in castor microsomes using 1-acyl-2-oleoyl-sn-glycero-3-phosphocholine as the substrate of oleoyl-12-hydroxylase. Lipids. 1998 Jan;33(1):59-69.
4. Turner C, He X, Nguyen T, Lin JT, Wong RY, Lundin RE, Harden L, McKeon T: Lipase-catalyzed methanolysis of triricinolein in organic solvent to produce 1,2(2,3)-diricinolein. Lipids. 2003 Nov;38(11):1197-206.
5. McKeon TA, Lin JT, Stafford AE: Biosynthesis of ricinoleate in castor oil. Adv Exp Med Biol. 1999;464:37-47.
6. Johnson W Jr: Final report on the safety assessment of trilaurin, triarachidin, tribehenin, tricaprin, tricaprylin, trierucin, triheptanoin, triheptylundecanoin, triisononanoin, triisopalmitin, triisostearin, trilinolein, trimyristin, trioctanoin, triolein, tripalmitin, tripalmitolein, triricinolein, tristearin, triundecanoin, glyceryl triacetyl hydroxystearate, glyceryl triacetyl ricinoleate, and glyceryl stearate diacetate. Int J Toxicol. 2001;20 Suppl 4:61-94.
7. Lin JT, Chen JM, Liao LP, McKeon TA: Molecular species of acylglycerols incorporating radiolabeled fatty acids from castor (Ricinus communis L.) microsomal incubations. J Agric Food Chem. 2002 Aug 28;50(18):5077-81.
8. Stubiger G, Pittenauer E, Allmaier G: Characterisation of castor oil by on-line and off-line non-aqueous reverse-phase high-performance liquid chromatography-mass spectrometry (APCI and UV/MALDI). Phytochem Anal. 2003 Nov-Dec;14(6):337-46.
9. Maeshima M, Beevers H: Purification and properties of glyoxysomal lipase from castor bean. Plant Physiol. 1985 Oct;79(2):489-93.
10. Lie Ken Jie MS, Syed-Rahmatullah MS: Chemical and enzymatic preparation of acylglycerols containing C18 furanoid fatty acids. Lipids. 1995 Jan;30(1):79-84.
11. He X, Chen GQ, Lin JT, McKeon TA: Regulation of diacylglycerol acyltransferase in developing seeds of castor. Lipids. 2004 Sep;39(9):865-71.
12. MOULE Y: [Significance of the action of temperature on the hydrolysis of triricinolein by lipase from ricin]. Bull Soc Chim Biol (Paris). 1953;35(8):759-70.
13. Turner C, Wani S, Wong R, Lin JT, McKeon T: Lipase-catalyzed esterification of 2-monoricinolein for 1,2 (2,3)-diricinolein synthesis. Lipids. 2006 Jan;41(1):77-83.
14. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50.
15. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.
16. 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.
17. 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.
18. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.
19. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
20. The lipid handbook with CD-ROM
21. Triglycerides and Cholesterol Research