Common NameErythrodiol
DescriptionErythrodiol 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 ).
Structure
Molecular FormulaC30H50O2
Average Mass442.72800
Monoisotopic Mass442.38108
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
Traditional Name(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-ol
CAS Registry Number545-48-2
SMILESCC1(C)CC[C@]2(CO)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1
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/t21-,22-,23+,24-,27-,28+,29+,30+/m0/s1
InChI KeyPSZDOEIIIJFCFE-OSQDELBUSA-N
CHEBI IDCHEBI:67939
HMDB IDHMDB0002360
StateNot Available
Water Solubility3.81e-04 g/l
logP6.75
logS-6.07
pKa (Strongest Acidic)18.92
pKa (Strongest Basic)-0.64
Hydrogen Acceptor Count2
Hydrogen Donor Count2
Polar Surface Area40.46 Ų
Rotatable Bond Count1
Physiological Charge0
Formal Charge0
Refractivity133.68 m³·mol⁻¹
Polarizability54.96

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