(3S,8R,9S,10R,13S,14S,16S)-3-hydroxy-10,13-dimethyl-17-oxo-16-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene

Base Information

• Chemical Name: (3S,8R,9S,10R,13S,14S,16S)-3-hydroxy-10,13-dimethyl-17-oxo-16-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene
• CAS No.: 4873-65-8
• Molecular Formula: C₁₉H₂₈O₆S
• Molecular Weight: 384.494
• Mol file: 4873-65-8.mol

Synonyms:(3S,8R,9S,10R,13S,14S,16S)-3-hydroxy-10,13-dimethyl-17-oxo-16-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene;3b,16a-Dihydroxyandrostenone sulfate

Chemical Property of (3S,8R,9S,10R,13S,14S,16S)-3-hydroxy-10,13-dimethyl-17-oxo-16-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene

Chemical Property:

• PSA: 109.28000
• Density: 1.37g/cm³
• LogP: 3.75790

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• General Description: The compound (3S,8R,9S,10R,13S,14S,16S)-3-hydroxy-10,13-dimethyl-17-oxo-16-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene, also known as 3β,16α-dihydroxyandrostenone sulfate, is a sulfated steroid derivative featuring hydroxyl groups at the 3β and 16α positions, a ketone at C17, and a sulfate ester at the 3β position. It is structurally related to 16α-hydroxylated androgens, which serve as key intermediates in estriol biosynthesis during pregnancy. (3S,8R,9S,10R,13S,14S,16S)-3-hydroxy-10,13-dimethyl-17-oxo-16-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene shares similarities with 16α-hydroxydehydroepiandrosterone 3-sulfate, suggesting a potential role in steroid metabolism or as a synthetic precursor for further modifications. However, the provided abstract does not explicitly discuss this specific compound, focusing instead on related 16α-hydroxylated androgens like 16α-hydroxyandrostenedione and 16α-hydroxytestosterone. **Return:** Null

Technology Process of (3S,8R,9S,10R,13S,14S,16S)-3-hydroxy-10,13-dimethyl-17-oxo-16-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene

There total 2 articles about (3S,8R,9S,10R,13S,14S,16S)-3-hydroxy-10,13-dimethyl-17-oxo-16-sulfooxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthrene 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:

→ Dehydroepiandrosteron-16α-hydroxy-3β-sulfonsaeure (1050-89-1,4873-65-8)

Guidance literature:

Dehydroepiandrosteron-?3b-sulfonsaeure, FeSO2*7H2O, EDTA*2Na, Ascorbinsaeure, Phosphatpuffer, evtl. H2O2 (4 Varianten);

Reference yield:

→ 3β,16α-Dihydroxy-17-oxoandrost-5-en-3β-yl sulfonsaeure (1050-89-1,4873-65-8)

Guidance literature:

Dihydroxyandrostenon VIII, Chlorsulfonsaeure, NH4OH;

DOI:10.1016/0039-128X(78)90063-6

Refernces

10.1016/0039-128X(78)90063-6

The research aims to develop a more efficient chemical synthesis method for 16α-hydroxylated androgens, which are crucial intermediates in the formation of estriol during pregnancy. Key chemicals used include 16α-bromoandrostenedione, which is converted to the hydrazone of 16α-hydroxyandrostenedione and then hydrolyzed to yield the desired compound. 16α-Hydroxyandrostenedione (16α-hydroxyandrost-4-ene-3,17-dione) is a steroid with a hydroxyl group at the 16α position and a ketone group at the 3 and 17 positions. The total yield of 16α-hydroxyandrostenedione from dehydroepiandrosterone is 38% via the hydrazone route, and 24% via the Jones' reagent oxidation route. 16α-Hydroxytestosterone (16α,17β-dihydroxyandrost-4-en-3-one) is a steroid with hydroxyl groups at the 16α and 17β positions and a ketone group at the 3 position. 16α-Hydroxydehydroepiandrosterone 3-sulfate (3β,16α-dihydroxyandrost-5-en-17-one 3-monosulfate) is a steroid with hydroxyl groups at the 3β and 16α positions, a ketone group at the 17 position, and a sulfate ester at the 3 position.