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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:20:41 UTC
Update Date2021-10-13 07:10:18 UTC
HMDB IDHMDB0038061
Secondary Accession Numbers
  • HMDB38061
Metabolite Identification
Common NameTriricinolein
DescriptionTriricinolein 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. Based on a literature review a significant number of articles have been published on Triricinolein.
Structure
Data?1563863134
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 Weight933.4303
Monoisotopic Molecular Weight932.768034926
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
CAS Registry Number2540-54-7
SMILES
CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(COC(=O)CCCCCCC\C=C/CC(O)CCCCCC)OC(=O)CCCCCCC\C=C\CC(O)CCCCCC
InChI Identifier
InChI=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
Ontology
Disposition

Source

Route of exposure

Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.7e-17 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.6e-05 g/LALOGPS
logP10(9.54) g/LALOGPS
logP10(16.35) g/LChemAxon
logS10(-7.4) g/LALOGPS
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+329.13831661259
DarkChem[M-H]-306.88731661259

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 10V, Positive-QTOFsplash10-0udi-0000000009-35430091881df10d355f2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 20V, Positive-QTOFsplash10-0udi-0000000009-35430091881df10d355f2017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 40V, Positive-QTOFsplash10-0019-0000009007-f3a695322ab20fc7ae652017-10-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 10V, Positive-QTOFsplash10-0a4i-0000000009-1036e4d459cbe7999daf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 20V, Positive-QTOFsplash10-0a4i-0000000009-1036e4d459cbe7999daf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 40V, Positive-QTOFsplash10-0a4i-0000000009-1036e4d459cbe7999daf2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 10V, Positive-QTOFsplash10-00kb-0000001096-1a82354c75ad069c55e62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 20V, Positive-QTOFsplash10-0002-0100000192-6ec621764fdc4c3131682021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 40V, Positive-QTOFsplash10-0gbj-1120008950-acbe512595b8978efd8b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 10V, Negative-QTOFsplash10-01q9-0030006019-1dfb61d3f0f4d8b69dac2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 20V, Negative-QTOFsplash10-02ea-0096008324-c84a42cc5b4114ac7af22021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 40V, Negative-QTOFsplash10-0002-1095008000-c3e719e29fb33cd3225c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 10V, Positive-QTOFsplash10-0udi-0000000009-dab299a260c09517b4cd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 20V, Positive-QTOFsplash10-0udi-0000000009-dab299a260c09517b4cd2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 40V, Positive-QTOFsplash10-0019-0010009007-b0ad1296ee0d66d15b8e2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 10V, Positive-QTOFsplash10-000i-0000000009-b214f3614079fb6bcb002021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 20V, Positive-QTOFsplash10-000i-0000000009-b214f3614079fb6bcb002021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Triricinolein 40V, Positive-QTOFsplash10-0a56-0009009009-d454d9ec18c34b630c582021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB017272
KNApSAcK IDC00057288
Chemspider ID35014503
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkRicinolein
METLIN IDNot Available
PubChem Compound131752288
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1368691
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:11800053 ]
  2. 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. [PubMed:19127716 ]
  3. Watson WC, Murray ES: Triricinolein synthesis in vivo. Biochim Biophys Acta. 1965 Oct 4;106(2):311-4. [PubMed:5867691 ]
  4. 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. [PubMed:9470174 ]
  5. 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. [PubMed:14733366 ]
  6. McKeon TA, Lin JT, Stafford AE: Biosynthesis of ricinoleate in castor oil. Adv Exp Med Biol. 1999;464:37-47. [PubMed:10335384 ]
  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. [PubMed:12188611 ]
  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. [PubMed:14667059 ]
  9. Maeshima M, Beevers H: Purification and properties of glyoxysomal lipase from castor bean. Plant Physiol. 1985 Oct;79(2):489-93. [PubMed:16664437 ]
  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. [PubMed:7760692 ]
  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. [PubMed:15669762 ]
  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. [PubMed:13126746 ]
  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. [PubMed:16555475 ]
  14. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  15. 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 ]
  16. 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 ]
  17. 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 ]
  18. Ghosh S, Strum JC, Bell RM: Lipid biochemistry: functions of glycerolipids and sphingolipids in cellular signaling. FASEB J. 1997 Jan;11(1):45-50. [PubMed:9034165 ]
  19. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  20. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.
  21. Linda T. Welson (2006). Triglycerides and Cholesterol Research. Nova Science Publishers Inc..