Erythrodiol

Base Information

• Chemical Name: Erythrodiol
• CAS No.: 545-48-2
• Molecular Formula: C₃₀H₅₀O₂
• Molecular Weight: 442.726
• European Community (EC) Number: 208-890-4
• UNII: 3VWF903FSS
• DSSTox Substance ID: DTXSID401015931
• Nikkaji Number: J13.880K
• Wikidata: Q27136414
• Metabolomics Workbench ID: 38140
• ChEMBL ID: CHEMBL400074
• Mol file: 545-48-2.mol

Synonyms:erythrodiol;olean-12-ene-3beta,28-diol

Chemical Property of Erythrodiol

Chemical Property:

• Melting Point: 230-231 °C(lit.)
• Boiling Point: 520.5 °C at 760 mmHg
• PKA: 15.09±0.10(Predicted)
• Flash Point: 209.9 °C
• PSA: 40.46000
• Density: 1.05 g/cm³
• LogP: 7.14130
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 442.381080833
• Heavy Atom Count: 32
• Complexity: 810

Purity/Quality:

98%min ^*data from raw suppliers

3β-Erythrodiol ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 2-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)CO)C
• Isomeric SMILES: C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)CO)C)C)(C)C)O
• Description: Erythrodiol 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.
• Uses: It 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.

Technology Process of Erythrodiol

There total 52 articles about Erythrodiol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

Oleanolic acid (508-02-1) → erythrodiol (545-48-2,55869-95-9,118204-21-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; Reflux;

DOI:10.3390/molecules23071552

Reference yield: 95.0%

(3β)-3-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-olean-12-en-28-ol (152487-61-1) → erythrodiol (545-48-2,55869-95-9,118204-21-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 55 ℃; for 12h;

DOI:10.1021/ja00072a064

Reference yield: 85.0%

ursolic acid (77-52-1) → erythrodiol (545-48-2,55869-95-9,118204-21-0)

Guidance literature:

ursolic acid; With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Reflux;

With water; In tetrahydrofuran;

DOI:10.1134/S1068162011030101

upstream raw materials:

myricadiol

Oleanolic acid

oleanolic acid methyl ester

sodium ethanolate

Downstream raw materials:

3-oxoolean-12-en-28-al

erythrodiol diacetate

3β-acetoxy-28-hydroxy-ole-12-ene

28-O-acetylerythrodiol

Refernces

• 1、 Serbian, Immo,Csuk, René. "An improved scalable synthesis of α- and β-amyrin". . . Retrieved 2018/07/13.
• 2、 Bian, Linglin,Cao, Shining,Cheng, Lihong,Nakazaki, Atsuo,Nishikawa, Toshio,Qi, Jianhua. "Semi-synthesis and Structure–Activity Relationship of Neuritogenic Oleanene Derivatives". supporting information. p. 1972 - 1977. Retrieved 2018/09/06.