Record Information
Version1.0
Creation date2010-04-08 22:10:29 UTC
Update date2015-07-20 22:55:39 UTC
Primary IDFDB013011
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameErythrodiol
DescriptionFound in grapes, olives, pot marigold (Calendula officinalis) and other plants Erythrodiol is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Erythrodiol exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. (PMID: 17292619, 15522132)
CAS Number545-48-2
Structure
Thumb
Synonyms
SynonymSource
(3beta)-Olean-12-ene-3,28-diolChEBI
3beta,28-Dihydroxy-ole-12-eneChEBI
3beta-ErythrodiolChEBI
Oleanolic alcoholChEBI
(3b)-Olean-12-ene-3,28-diolGenerator
(3β)-olean-12-ene-3,28-diolGenerator
3b,28-Dihydroxy-ole-12-eneGenerator
3β,28-dihydroxy-ole-12-eneGenerator
3b-ErythrodiolGenerator
3β-erythrodiolGenerator
Olean-12-ene-3beta,28-diolHMDB
Erythrodioldb_source
Homoolestranoldb_source
Predicted Properties
PropertyValueSource
Water Solubility0.00038 g/LALOGPS
logP6.75ALOGPS
logP6.12ChemAxon
logS-6.1ALOGPS
pKa (Strongest Acidic)18.92ChemAxon
pKa (Strongest Basic)-0.64ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity133.68 m³·mol⁻¹ChemAxon
Polarizability54.94 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC30H50O2
IUPAC name(3S,4aR,6aR,6bS,8aS,12aS,14aR,14bR)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicen-3-ol
InChI IdentifierInChI=1S/C30H50O2/c1-25(2)14-16-30(19-31)17-15-28(6)20(21(30)18-25)8-9-23-27(5)12-11-24(32)26(3,4)22(27)10-13-29(23,28)7/h8,21-24,31-32H,9-19H2,1-7H3
InChI KeyPSZDOEIIIJFCFE-UHFFFAOYSA-N
Isomeric SMILESCC1(C)CCC2(CO)CCC3(C)C(=CCC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1
Average Molecular Weight442.7168
Monoisotopic Molecular Weight442.381080844
Classification
DescriptionThis compound belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentTriterpenoids
Alternative Parents
Substituents
  • Triterpenoid
  • Cyclic alcohol
  • Secondary alcohol
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 81.39%; H 11.38%; O 7.23%DFC
Melting PointMp 235-237°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D +77DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-0123900000-3a7f6f3413b211be9345View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-1011190000-e7cc02cd8b4d770be9bdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004l-0000900000-1b374c58d66d9020e78cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-056r-1232900000-b89492002c0fe40b2c91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-3797100000-3e2b5350d905fe776bf6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0000900000-678861a933ce5d5e671cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-0001900000-648a4f20a134ca0d34e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0005-1009500000-7e531b41f33010f6c3e6View in MoNA
ChemSpider ID91945
ChEMBL IDCHEMBL400074
KEGG Compound IDNot Available
Pubchem Compound ID101761
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02360
CRC / DFC (Dictionary of Food Compounds) IDHNT00-A:HNT08-I
EAFUS IDNot Available
Dr. Duke IDERYTHRODIOL
BIGG IDNot Available
KNApSAcK IDC00019065
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
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).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.