(3beta)-Olean-12-ene-3,28-diol
Basic information
- CAS
545-48-2- Standard SMILES
CC1(C)CC[C@]2(CO)CC[C@]3(C)C(=CCC4[C@@]5(C)CC[C@H](O)C(C)(C)C5CC[C@]43C)C2C1- InChIKey
PSZDOEIIIJFCFE-QXSRUYARSA-N- Molecular formula
- C30H50O2
- Average molar mass
- 442.7 g/mol
- Monoisotopic mass
- 442.38108083
Names & identifiers
- Preferred name
- (3beta)-Olean-12-ene-3,28-diol
- IUPAC
- (3S,6aR,6bS,8aS,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
- English name
- Erythrodiol
- Molecular formula
- C30H50O2
- Molecular weight
- 442.72
Names & synonyms
(3s,6ar,6bs,8as,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(3.beta.)-Olean-12-ene-3,28-diolNCGC00488761-01olean-12-ene-3β,28-diolAids064685ERYTHODIOLAids-064685ERYTHRODIOLERYTHRODIOL(P)HOMOOLESTRANOL3β-ErythrodiolErythrodiol-RM
Show more names
3b-Erythrodiol
Database identifiers
- CAS
545-48-2- PubChem CID
- 470261
- Nikkaji
- J2.137.424E
Properties
Computed structural properties
- XLogP
- 7.6
- Topological polar surface area
- 40.5 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 1
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 810
Physicochemical properties
- Melting point
- 230 · 230-231 °C(lit.)
- Boiling point
- 520.5 · 520.5±50.0 °C(Predicted)
- Density
- 1.05 · 1.05±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C Freezer, Under inert atmosphere
- solubility
- Chloroform (Slightly, Sonicated), Methanol (Slightly)
- pka
- 15.09 · 15.09±0.10(Predicted)
- form
- Solid
- color
- White to Off-White
- Water Solubility
- insoluble in water
- BRN
- 2340203 · 2340203
- Major Application
- food and beverages
- Cosmetics Ingredients Functions
- ANTIOXIDANTSKIN CONDITIONING
- InChIKey
- PSZDOEIIIJFCFE-MMIPUHLFNA-N
- SMILES
- [C@@]12(C)CC[C@@]3(CO)CCC(C)(C)C[C@@]3([H])C1=CC[C@]1([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]21C |&1:0,4,13,18,20,24,29,33,r|
- LogP
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- F
- 10-23
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 2-45
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Precautionary statements
- P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313
Chemistry & industry
Applications
DescriptionErythrodiol is a triterpene that has been found in olive oil and has diverse biological activities. It induces relaxation of isolated rat aortic rings precontracted with phenylephrine (EC50 = 3.38 μM). Erythrodiol inhibits the growth of HT-29 adenocarcinoma cells (EC50 = 48.8 μM). It induces production of reactive oxygen species (ROS) and apoptosis in MCF-7 cells when used at a concentration of 100 μM. Topical administration of erythrodiol (0.5 mg/ear) reduces ear edema and myeloperoxidase (MPO) activity induced by phorbol 12-myristate 13-acetate (TPA; ) in mice.
UsesIt is an essential reagent in the synthesis of aminopropoxytriterpenoids that have anticancer activity. 3β-Erythrodiol has pharmacological property as a vasodilatory agent. It may have interesting therapeutic potential as a new vasodilator drug, for protecting the cardiovascular system.
Additional notes
DefinitionChEBI: Erythrodiol is a pentacyclic triterpenoid that is beta-amyrin in which one of the hydrogens of the methyl group at position 28 has been replaced by a hydroxy group. It is a plant metabolite found in olive oil as well as in Rhododendron ferrugineum and other Rhododendron species. It has a role as a plant metabolite. It is a pentacyclic triterpenoid, a primary alcohol, a secondary alcohol and a diol. It is functionally related to a beta-amyrin.
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