80735-62-2

Upstream product

• 83-48-7 Stigmasterol 
• 108-24-7 acetic anhydride 
• 33761-96-5 acetate of (24S)-ethylcholesta-5,22,25-triene-3β-ol 
• 75-36-5 acetyl chloride 
• 19716-26-8 daucosterol 
• 1371577-45-5 stigmasterol-3-O-β-D-arabinopyranosyl [1->4]-O-β-D-glucopyranoside 
• 33644-13-2 (24S)-24-ethylcholesta-5,22(E),25-trien-3β-ol 

Downstream Products

• 55724-18-0 3β-Acetoxy-5α-chlor-stigmast-22-en 
• 76740-15-3 (S)-2-ethyl-3-methylbutanal 
• 32212-73-0 5α,6β-dibromostigmastan-3β-yl acetate 
• 915-05-9 stigmast-5-en-3-yl acetate 
• 53906-49-3 3β-ol-23,24-bisnor-chol-5-en-22-al hemihydrochloride 
• 604-35-3 Cholesteryl acetate 
• 809-51-8 7-ketocholesteryl acetate 
• 1059-86-5 7-Dehydrocholesteryl acetate 
• 434-16-2 7-dehydrocholesterol 
• 67-97-0 vitamin D₃ 
• 91237-67-1 (R)-2-ethyl-3-methyl-butyraldehyde 
• 92034-97-4 (R)-3-methyl-2-ethyl-butyraldehyde-(2,4-dinitro-phenylhydrazone) 
• 50633-49-3 acetic acid-(22ξ.23ξ-dibromo-24α_FH-stigmasten-(5)-yl-(3β)-ester) 
• 6160-48-1 O-(3.5-dinitro-benzoyl)-poriferastanol 

Relevant academic research and scientific papers

Mild and selective deprotection method of acetylated steroids and diterpenes by dibutyltin oxide

Dibutyltin oxide (DBTO) was first utilized for the deacetylation of steroid and diterpene esters. The results showed the deprotection of acetylated steroids and diterpenes separately with moderate catalysis dibutyltin oxide in methanol selectively removed part acetyl groups of these substrates, whereas several functional groups of the steroids and diterpenes were retained and neither isomerization nor degradation of these substrates was observed. It seems that the acetyl groups with lower steric hindrance or near carbonyl, alkoxy, or hydroxyl groups can be cleaved by the reaction, whereas the acetyl groups with higher steric hindrance or without carbonyl, alkoxy, or hydroxyl groups neighboring were retained under the same conditions. One of the interesting results obtained was the selective hydrolysis of the 3β-O-acetyl group in the presence of the 6β group in 3β,6β-Di-O-acetyl-5α-hydroxypregn-16-en-20-one. This allows for subsequent introduction of one unit at C-3 and the other unit at C-6. This procedure is useful for the synthesis of a series of closely related isomers of 3β,5α,6β-trihydroxypregn-16-en-20-one and other widespread polyhydroxysteroids in marine organisms and some terrestrial species.

Novel industrial method for preparing vitamin D3 by taking stigmasterol as raw material

The invention provides a novel industrial method for preparing vitamin D3 by taking stigmasterol as a raw material. The method comprises the following steps: sequentially carrying out hydroxyl acetylation, side chain oxidation, side chain isopentane reduction and hydrogenation on stigmasterol to obtain cholesterol acetate, and then sequentially carrying out oxidation, hydrazone formation, hydrazone removal, hydrolysis, illumination and the like to obtain the vitamin D3. The invention provides a novel method for preparing vitamin D3 from stigmasterol, and the method has the advantages of mild reaction conditions and high yield, and is suitable for industrial production.

Absolute configuration assignment of stigmasterol oxiranes

Diastereoisomeric stigmasterol oxiranes 4, 5, 8, and 9 are known phytosterol oxidation products (POPs) that have been evaluated for their cytotoxicity, although the results are of limited significance since, in most cases, they were evaluated as mixtures. Consequently, to establish biological activity hierarchy of these oxides, it is critical to evaluate individual pure POPs. Therefore, we now describe the obtention of individual molecules and their absolute configuration (AC) determination. The two acetylated C-5?C-6 oxiranes 6 and 7; the two acetylated C-22?C-23 oxides 10 and 11, obtained by means of Δ5 double bond protection-deprotection; and the four C-5?C-6, C-22?C-23 diepoxystigmasteryl acetates 19–22 were now individually gained and their AC determined by vibrational circular dichroism. Vibrational modes associated with the C-5?C-6 and the C-22?C-23 bonds were identified in dioxiranes 19–22 and used to assign the AC of monoepoxides 6, 7, 10, and 11. The AC of biological active non-acetylated molecules follows immediately. Due to the scarce spectroscopic information available for these POPs, the 1H and 13C NMR chemical shifts of 3–22 were assigned using 1D- and 2D-NMR experiments.

Synthesis and search for 3β,3′β-disteryl ethers after high-temperature treatment of sterol-rich samples

It has been proven that at increased temperature, sterols can undergo various chemical reactions e.g., oxidation, dehydrogenation, dehydration and polymerisation. The objectives of this study are to prove the existence of dimers and to quantitatively analyse the dimers (3β,3′β-disteryl ethers). Sterol-rich samples were heated at 180 °C, 200 °C and 220 °C for 1 to 5 h. Quantitative analyses of the 3β,3′β-disteryl ethers were conducted using liquid extraction, solid-phase extraction and gas chromatography coupled with mass spectrometry. Additionally, for the analyses, suitable standards were synthetized from native sterols. To identify the mechanism of 3β,3′β-disteryl ether formation at high temperatures, an attempt was made to use the proposed synthesis method. Additionally, due to the association of sterols and sterol derivatives with atherosclerosis, preliminary studies with synthetized 3β,3′β-disteryl ethers on endothelial cells were conducted.

Synthesis and cytotoxicity of new stigmasterol derivatives

This study identifies potential antitumor compounds from a series of new stigmasterol derivatives. Eleven stigmasterol derivatives were synthesized and their structures were confirmed by 1H NMR, MS, and elemental analyses. Their cytotoxicity in vitro against three human cancer cell lines (MCF-7, A549 and HepG2) were evaluated by the MTT assay. Among these compounds, AB-5 and AB-11 shows much better cytotoxicity against MCF-7, A549, and HepG2 cells, and AB-10 exhibits selective cytotoxicity against MCF-7. Their structure-activity relationships were also investigated. In conclusion, AB-5, AB-10 and AB-11 serve as potential compounds for the new generation of anticancer drugs.

Phytochemical investigation and characterization of isolated chemical constituents from Kyllinga triceps Rottb.

Four compounds have been isolated by column chromatography from Kyllinga triceps namely quercetin dihydrate (1), rutin (2), β-sitosterol (3) and stigmasterol (4). Their structures have been elucidated by, FTIR, HR-EIMS, 1H NMR and 13C NMR spectroscopic studies.

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.

TiCl4/Et3N-Mediated Condensation of Acetate and Formate Esters: Direct Access to β-Alkoxy- and β-Aryloxyacrylates

A methodology to build (E)-β-alkoxy- and (E)-β-aryloxyacrylate moieties from acetate and formate esters promoted by the TiCl4/Et3N system is presented. The reaction is compatible with a broad range of structural skeletons and elapses through an unusual condensation pathway. Taking into account the obtained results, we propose a plausible mechanism involving a bimetallic titanium intermediate for this type of transformation.

22-abeo-stigmasterol benzimidazole compound as well as preparation method and application thereof

The invention discloses a 22-abeo-stigmasterol benzimidazole compound as well as a preparation method and application thereof. The structural formula of the 22-abeo-stigmasterol benzimidazole compound is shown in the specification; experiments for in-vitro inhibition of growth and proliferation activities of cancer cells show that the 22-abeo-stigmasterol benzimidazole compound prepared by the preparation method has remarkable inhibition effect to multiple tumor cell strains such as human papillary thyroid cancer cells, human oral epidermoid carcinoma cells, cancer cell strains of cervical cancer and the like. Meanwhile, the 22-abeo-stigmasterol benzimidazole compound has no cytotoxicity to human kidney epithelial cells (HEK293T) and can be applied to the preparation of drugs for treating cancers.