32212-73-0

Usage

Uses

Used in Pharmaceutical Industry:
5α,6β-Dibromostigmastan-3β-yl 3-Acetate is used as a reactant in the preparation of methylenecholestendiol, a synthetic steroidal compound with potential therapeutic applications. It is also used in the synthesis of phytosterols, which are plant-derived compounds that have cholesterol-lowering properties and can be used in the development of drugs for treating hypercholesterolemia and other cardiovascular diseases.
Used in Chemical Research:
As a white solid with distinct chemical properties, 5α,6β-Dibromostigmastan-3β-yl 3-Acetate can be utilized in chemical research for studying the effects of bromination and acetylation on the stigmasterol molecule. This can provide insights into the structure-activity relationships of related compounds and contribute to the development of new pharmaceutical agents or other applications.
Used in Cosmetics Industry:
Due to its chemical stability and potential biological activity, 5α,6β-Dibromostigmastan-3β-yl 3-Acetate may find use in the cosmetics industry as an ingredient in skincare products. It could potentially be incorporated into formulations for its moisturizing, anti-inflammatory, or other beneficial properties, depending on further research and development.

Upstream product

• 67-66-3 chloroform 
• 4651-48-3 acetic acid stigmasteryl ester 
• 7726-95-6 bromine 
• 83-48-7 Stigmasterol 
• 4651-48-3 stigmasterol acetate 

Downstream Products

• 53-43-0 dehydroepiandrosterone 
• 145-13-1 Pregnenolone 
• 1474-14-2 3β-acetoxybisnor-5-cholenic acid 
• 53906-49-3 3β-ol-23,24-bisnor-chol-5-en-22-al hemihydrochloride 
• 10211-88-8 (20S)-3β-acetoxybisnorchol-5-en-22-al 
• 58526-32-2 3β-acetoxy-20(S)-5α-bisnorcholanic acid 

Relevant academic research and scientific papers

Synthesis of some steroidal derivatives with side chain of 20-and 22-hydrazone aromatic heterocycles and their antiproliferative activity

Background: The modification of steroidal structure is commonly used to change the biological activity of steroids in medicinal chemistry. Some steroids containing heterocycles exhibit distinct cytotoxicity against various cancer cell lines and have been receiving wide attention over the years by medicinal chemists for drug discovery. Methods: Using pregnenolone and stigmasterol as starting materials, via different chemical reaction, two series of heterosteroids with side chain of 20- and 22-hydrazone aromatic cycles or heterocycles in their structures were synthesized and characterized by IR, NMR and HRMS. The antiproliferative activity of the compounds in vitro was evaluated against human HT-29, HeLa, Bel 7404 and SGC 7901 cancer cells by MTT assays. Results: The steroidal compounds with side chain of 20-hydrazone aromatic cycles or heterocycles exhibited distinct cytotoxicity. However, analogues with the side chain of 22-hydrazone resulted in a dramatic decrease of the cytotoxicity. The result of Annexin V assay showed that the 20-hydrazone compounds were potent apoptotic inducers against these carcinoma cells. Conclusion: Steroidal compounds with the side-chain of 20-hydrazone aromatic heterocycles exhibit distinct antiproliferative activity in vitro. However, the compounds with the side-chain of 22-hydrazone aromatic heterocycle decreased the cytotoxicity of the compounds.

NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF

Provided are methods of evaluating or treating a patient, e.g., a patient having a disorder described herein, comprising: a) optionally, acquiring a patient sample; b) acquiring an evaluation of and/or evaluating the sample for an alteration in the level S24(S)-hydroxycholesterol compared to a reference standard.

NEUROACTIVE STEROIDS, COMPOSITIONS, AND USES THEREOF

Compounds are provided according to Formula (I) and pharmaceutically acceptable salts thereof, wherein Z is a group of the formula (i), (ii), (iii), (iv), or (v), and wherein L1, L2, L3, X1, X2, Y, Rz4, Rz5, Rz6, n, R1, R2, R3a, R3b, R4a, R4b, R6a, R6b, R7a, R7b, R11a, R11b, R14, R17, R19, R20, R23a, R23b, and R24 are as defined herein, and pharmaceutical compositions thereof. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of CNS-related conditions in mammals.

Synthesis of polyhydroxysterols (I): Synthesis of 24-methylenecholest-4-en-3β,6β-diol, a cytotoxic natural hydroxylated sterol

Starting from stigmasterol (2), 24-methylenecholest-4-en-3β,6β-diol (1), a cytotoxic natural dihydroxylated sterol, was synthesized via 10 steps in 20% overall yield. The introduction of a side-chain of sterol was achieved by solid-liquid phase-transfer Wittig reaction using (3-methyl-2-oxo)butyltriphenylarsonium bromide (12) and K2CO3. Construction of the steroidal nucleus was finished by the addition of 3β-acetoxycholest-5,6-en-24-one (7) with NBA in dioxane under ambient temperature and by the elimination of 3β, 6β-diacetoxy-5a-bromocholestane-24-one (9). The spectral data of the synthetic product (1) are completely consistent with those of the natural compound (1). Copyright (C) 2001 Elsevier Science Inc.