3862-25-7

Usage

Uses

Used in Pharmaceutical Industry:
(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one is used as a pharmaceutical agent for its potential therapeutic effects. Its unique structure and functional groups may contribute to its bioactivity, making it a candidate for the development of new drugs targeting various diseases and conditions.
Used in Cosmetic Industry:
In the cosmetic industry, (7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one may be used as an active ingredient in skincare products due to its potential antioxidant, anti-inflammatory, and moisturizing properties. These properties can contribute to the improvement of skin health and appearance.
Used in Research and Development:
(7R,8S,9S,10R,13R,14S,17R)-7-hydroxy-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one is also used in research and development for its potential applications in various fields. Scientists and researchers may study its chemical properties, biological activities, and interactions with other compounds to explore its potential uses in medicine, agriculture, and other industries.

InChI:InChI=1/C27H44O2/c1-17(2)7-6-8-18(3)21-9-10-22-25-23(12-14-27(21,22)5)26(4)13-11-20(28)15-19(26)16-24(25)29/h15,17-18,21-25,29H,6-14,16H2,1-5H3/t18-,21-,22+,23+,24-,25+,26+,27-/m1/s1

Upstream product

• 604-35-3 Cholesteryl acetate 
• 1448262-85-8 7α-formyloxy-4-cholesten-3-one 
• 6544-51-0 cholest-4-en-7α-ol 
• 19317-90-9 7α-hydroxycholest-5-en-3β-yl 3-acetate 
• 809-51-8 7-ketocholesteryl acetate 

Downstream Products

• 1254-03-1 7α,12α-dihydroxy-4-cholesten-3-one 

Relevant academic research and scientific papers

Chemical synthesis of 7α-hydroxycholest-4-en-3-one, a biomarker for irritable bowel syndrome and bile acid malabsorption

7α-Hydroxy-cholest-4-en-3-one is a biomarker for bile acid loss, irritable bowel syndrome, and other diseases associated with defective bile acid biosynthesis. Furthermore, 7α-hydroxy-cholest-4-en-3-one is the physiological substrate for cytochrome P450 8B1 (P450 8B1 or CYP8B1), the oxysterol 12α-hydroxylase enzyme implicated in obesity and cardiovascular health. We report the chemical synthesis of this physiologically important oxysterol beginning with cholesterol. The key feature of this synthesis involves a regioselective C3-allylic oxidation of a 3-desoxy-Δ4-7α-formate steroid precursor to form 7α-formyloxy-cholest-4-en-3-one, which was saponified to yield 7α-hydroxy-cholest-4-en-3-one.

Identification of unusual oxysterols and bile acids with 7-oxo or 3,5,6-trihydroxy functions in human plasma by charge-tagging mass spectrometry with multistage fragmentation

7-Oxocholesterol (7-OC), 5,6-epoxycholesterol (5,6-EC), and its hydrolysis product cholestane-3,5,6-triol (3,5,6-triol) are normally minor oxysterols in human samples; however, in disease, their levels may be greatly elevated. This is the case in plasma from patients suffering from some lysosomal storage disorders, e.g., Niemann-Pick disease type C, or the inborn errors of sterol metabolism, e.g., Smith-Lemli-Opitz syndrome and cerebrotendinous xanthomatosis. A complication in the analysis of 7-OC and 5,6-EC is that they can also be formed ex vivo from cholesterol during sample handling in air, causing confusion with molecules formed in vivo. When formed endogenously, 7-OC, 5,6-EC, and 3,5,6-triol can be converted to bile acids. Here, we describe methodology based on chemical derivatization and LC/MS with multistage fragmentation (MSn) to identify the necessary intermediates in the conversion of 7-OC to 3-hydroxy-7-oxochol-5-enoic acid and 5,6-EC and 3,5,6-triol to 3,5,6-trihydroxycholanoic acid. Identification of intermediate metabolites is facilitated by their unusual MSn fragmentation patterns. Semiquantitative measurements are possible, but absolute values await the synthesis of isotope-labeled standards.—Griffiths, W. J., I. Gilmore, E. Yutuc, J. Abdel-Khalik, P. J. Crick, T. Hearn, A. Dickson, B. W. Bigger, T. H-Y. Wu, A. Goenka, A. Ghosh, S. A. Jones, and Y. Wang. Identification of unusual oxysterols and bile acids with 7-oxo or 3,5,6-trihydroxy functions in human plasma by charge-tagging mass spectrometry with multistage fragmentation.