5976-65-8

Basic information

• Product Name: 3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-4,17-diol
• Synonyms: 2-Hydroxyestradiol-3-methylether;3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-4,17-diol
• CAS NO: 5976-65-8
• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 0
• Mol File: 5976-65-8.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-4,17-diol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-4,17-diol(5976-65-8)
• EPA Substance Registry System: 3-methoxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-4,17-diol(5976-65-8)

Safety Data

• Hazardous Substances Data: 5976-65-8(Hazardous Substances Data)

Usage

Classification

Steroid derivative

Occurrence

Naturally produced in the human body and found in certain plants

Physiological Role

Regulates the immune system
Modulates inflammation

Therapeutic Potential

Investigated for treating cancer
Investigated for treating autoimmune diseases

Chemical Structure Features

Substituents:
3-methoxy
13-methyl
Ring Structure:
6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene
Functional Groups:
Hydroxyl groups at positions 4 and 17 (diol)

Drug Development Target

Potential target for drug development

Research Significance

Subject of research for new medical treatments

Upstream product

• 50-28-2 estradiol 
• 1028058-66-3 2-formyl-3-methoxyestra-1,3,5(10)-trien-17β-acetate 
• 52717-99-4 2-Hydroxy-oestradiol-3-methylaether-17-acetat 
• 186581-53-3 diazomethane 
• 37492-84-5 2-Hydroxy-oestradiol-2-benzoat 
• 84523-21-7 potassium 2-hydroxy-3-methoxyestra-1,3,5(10)-trien-17β-yl sulfate 
• 84510-01-0 potassium <2-hydroxy-3-methoxyestra-1,3,5(10)-trien-17β-yl-β-D-glucopyranosid>uronate 
• 116382-71-9 Sodium; (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-((8R,9S,13S,14S,17S)-17-hydroxy-3-methoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-2-yloxy)-tetrahydro-pyran-2-carboxylate 
• 362-05-0 2-Hydroxyestradiol 
• 84509-99-9 potassium 2-benzoyloxy-3-methoxyestra-1,3,5(10)-trien-17β-yl sulfate 
• 27736-76-1 sodium (3,17β-dihydroxy-1,3,5(10)-estratrien-2-yl β-D-glucopyranosid)uronate 
• 116382-67-3 methyl (4-bromo-3-hydroxy-17-oxo-1,3,5(10)-estratrien-2-yl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 116382-68-4 methyl (3,17β-dihydroxy-1,3,5(10)-estratrien-2-yl 2,3,4-tri-O-acetyl-β-D-glucopyranosid)uronate 
• 84509-98-8 2-benzoyloxy-3-methoxyestra-1,3,5(10)-trien-17β-ol 

Downstream Products

• 362-05-0 2-Hydroxyestradiol 
• 116282-36-1 2-hydroxyestrone 2,3-dibenzoate 
• 362-06-1 2-hydroxyestrone 
• 84509-98-8 2-benzoyloxy-3-methoxyestra-1,3,5(10)-trien-17β-ol 
• 5976-67-0 17beta-Estradiol 2,3-dimethyl ether 

Relevant articles and documents

A simple, convenient and chemoselective formylation of sterols by Vilsmeier reagent

Vilsmeier reagent (DMF-POCl3) was used as an efficient formylating agent. Several sterols having sec-hydroxyl group at 3/17-position have been modified into respective formate esters. The method is simple, mild, chemoselective and provides sec-alcoholic protection in good yields.

Methylation of catechol estrogen with diazomethane

Dynamic aspects of methylation of catechol estrogen with diazomethane were investigated by means of thin-layer chromatography. The methylation rate of the hydroxyl group at the C-3 position was almost the same as that of the C-2 hydroxyl group in the reaction of 2-hydroxyestrogen, and 2-3 times that of the C-4 hydroxyl group in the reaction of 4-hydroxyestrogen. In these experiments, the maximum yields of 2-methoxyestrone, 2-hydroxyestrone 3-methyl ether, 4-methoxyesterone and 4-hydroxyesterone 3-methyl ether were 32, 39, 13, and 70%, respectively. In addition, demethylation of catechol estrogen dimethyl ethers with boron tribromide and synthesis of 4-hydroxyestrone monomethyl ethers are described.