64284-64-6

Basic information

• Product Name: (3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol
• Synonyms: (3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol;4,4-Dimethylcholesta-8,14,24-trienol;(3β,5α)-4,4-DiMethylcholesta-8,14,24-trien-3-ol (Contain up to 15% 25 isoMer);4,4-DiMethyl-5α-cholesta-8,14,24-trien-3β-ol;FF-MAS;Follicular Fluid Meiosis-activating Sterol;4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol
• CAS NO: 64284-64-6
• Molecular Formula: C29H46O
• Molecular Weight: 410.67
• Product Categories: Activators;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 64284-64-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 512.6°C at 760 mmHg
• Flash Point: 221.9°C
• Appearance: /
• Density: 1g/cm³
• Vapor Pressure: 1.19E-12mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: (3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol(64284-64-6)
• EPA Substance Registry System: (3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol(64284-64-6)

Safety Data

• Hazardous Substances Data: 64284-64-6(Hazardous Substances Data)

Usage

Description

(3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol is a complex organic compound with a unique molecular structure. It is characterized by its multiple chiral centers and methyl groups, as well as its decahydrocyclopenta[a]phenanthren-3-ol core. (3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol has potential applications in various fields due to its unique properties.

Uses

Used in Pharmaceutical Industry:
(3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol is used as a pharmaceutical agent for its potential therapeutic effects. Its unique molecular structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs.
Used in Cosmetic Industry:
In the cosmetic industry, (3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol is used as an active ingredient in skincare products. Its unique properties may contribute to improved skin health and appearance, making it a valuable addition to cosmetic formulations.
Used in Research and Development:
(3R,5S,10S,13S,17S)-4,4,10,13-tetramethyl-17-[(2R)-6-methylhept-5-en-2-yl]-1,2,3,5,6,7,11,12,16,17-decahydrocyclopenta[a]phenanthren-3-ol is also used in research and development for its potential applications in various fields. Its unique structure and properties make it an interesting subject for scientific investigation, which may lead to the discovery of new uses and applications.

InChI:InChI=1/C29H46O/c1-19(2)9-8-10-20(3)22-12-13-23-21-11-14-25-27(4,5)26(30)16-18-29(25,7)24(21)15-17-28(22,23)6/h9,13,20,22,25-26,30H,8,10-12,14-18H2,1-7H3/t20-,22-,25+,26+,28-,29-/m1/s1

Upstream product

• 24470-78-8 isopropyltriphenylphosphonium iodide 
• 250256-50-9 (R)-4-((3S,5R,10S,13R,17R)-3-Hydroxy-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-pentanal 
• 79-63-0 tirucallol 
• 117439-06-2 Benzoic acid (3S,5R,10S,13R,17R)-17-[(R)-1,5-dimethyl-4-(2,2,2-trifluoro-acetoxy)-hexyl]-4,4,10,13-tetramethyl-15-trifluoromethanesulfonyloxy-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117438-85-4 (3β,5α,24R,S)-4,4-Dimethylcholesta-8,14-diene-3,24-diol 3-benzoate 24-trifluoroacetate 
• 117438-89-8 (3β,5α,24R,S)-3-(Benzoyloxy)-4,4-dimethyl-24-(trifluoroacetoxy)cholest-8(14)-en-15-one 
• 209850-48-6 Benzoic acid (3S,5R,9R,10R,13R,17R)-17-((S)-2-hydroxy-1,5-dimethyl-4-oxo-hexyl)-4,4,10,13-tetramethyl-15-oxo-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117438-96-7 Benzoic acid (3S,5R,9R,10R,13R,17R)-17-((E)-(R)-1,5-dimethyl-4-oxo-hex-2-enyl)-4,4,10,13-tetramethyl-15-oxo-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 
• 117438-97-8 3β-(Benzoyloxy)-4,4-dimethyl-5α-cholest-8(14)-ene-15,24-dione 
• 103751-19-5 (3β,5α,22E)-3-(benzoyloxy)-4,4-dimethylergosta-8(14),22-dien-15-one 
• 209850-50-0 3β-(Benzoyloxy)-24-hydroxy-4,4-dimethyl-5α-cholest-8(14)-ene-15-one 
• 117438-93-4 (3β,5α,20S)-3-(Benzoyloxy)-4,4-dimethyl-15-oxopregn-8,14-ene-20-carboxaldehyde 
• 563-80-4 3-methyl-butan-2-one 
• 204139-82-2 Acetic acid (3S,5R,9R,10R,13R,17R)-17-((R)-1,5-dimethyl-hex-4-enyl)-4,4,10,13-tetramethyl-15-oxo-2,3,4,5,6,7,9,10,11,12,13,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl ester 

Relevant articles and documents

The investigational drug VT-1129 is a highly potent inhibitor of Cryptococcus species CYP51 but only weakly inhibits the human enzyme

Cryptococcosis is a life-threatening disease often associated with HIV infection. Three Cryptococcus species CYP51 enzymes were purified and catalyzed the 14α-demethylation of lanosterol, eburicol, and obtusifoliol. The investigational agent VT-1129 bound tightly to all three CYP51 proteins (dissociation constant [Kd] range, 14 to 25 nM) with affinities similar to those of fluconazole, voriconazole, itraconazole, clotrimazole, and ketoconazole (Kd range, 4 to 52 nM), whereas VT-1129 bound weakly to human CYP51 (Kd, 4.53 μM). VT-1129 was as effective as conventional triazole antifungal drugs at inhibiting cryptococcal CYP51 activity (50% inhibitory concentration [IC50] range, 0.14 to 0.20 μM), while it only weakly inhibited human CYP51 activity (IC50, ～600 μM). Furthermore, VT-1129 weakly inhibited human CYP2C9, CYP2C19, and CYP3A4, suggesting a low drug-drug interaction potential. Finally, the cellular mode of action for VT-1129 was confirmed to be CYP51 inhibition, resulting in the depletion of ergosterol and ergosta-7-enol and the accumulation of eburicol, obtusifolione, and lanosterol/obtusifoliol in the cell membranes.

Functional importance for developmental regulation of sterol biosynthesis in Acanthamoeba castellanii

The sterol metabolome of Acanthamoeba castellanii (Ac) yielded 25 sterols. Substrate screening of cloned AcCYP51 revealed obtusifoliol as the natural substrate which converts to ?8,14-sterol (2H3-methyl]methionine incubation to intact cultures showing C28-ergosterol incorporates 2-2H atoms and C29-7-dehydroporiferasterol incorporates 5 2H-atoms, the natural distribution of sterols, CYP51 and previously published sterol methyltransferase (SMT) data indicate separate ?24(28)- and ?25(27)-olefin pathways to C28- and C29-sterol products from the protosterol cycloartenol. In cell-based culture, we observed a marked change in sterol compositions during the growth and encystment phases monitored microscopically and by trypan blue staining; trophozoites possess C28/C29-?5,7-sterols, viable encysted cells (mature cyst) possess mostly C29-?5-sterol and non-viable encysted cells possess C28/C29-?5,7-sterols that turnover variably from stress to 6-methyl aromatic sterols associated with changed membrane fluidity affording lysis. An incompatible fit of steroidal aromatics in membranes was confirmed using the yeast sterol auxotroph GL7. Only viable cysts, including those treated with inhibitor, can excyst into trophozoites. 25-Azacycloartanol or voriconazole that target SMT and CYP51, respectively, are potent enzyme inhibitors in the nanomolar range against the cloned enzymes and amoeba cells. At minimum amoebicidal concentration of inhibitor amoeboid cells rapidly convert to encysted cells unable to excyst. The correlation between stage-specific sterol compositions and the physiological effects of ergosterol biosynthesis inhibitors suggests that amoeba fitness is controlled mainly by developmentally-regulated changes in the phytosterol B-ring; paired interference in the ?5,7-sterol biosynthesis (to ?5,7) - metabolism (to ?5 or 6-methyl aromatic) congruence during cell proliferation and encystment could be a source of therapeutic intervention for Acanthamoeba infections.

Synthesis of FF-MAS from lithocholic acid

An effective synthesis of 4,4 dimethyl-cholest-8,14,24-trien-3β-ol (FF-MAS) from lithocholic acid is described, utilising a double oxidation and regioselective Wittig reaction as key steps. (C) 2000 Elsevier Science Ltd. All rights reserved.

Process for the production of 4,4-dimethyl-5α-cholesta-8,14,24-trien-3β-01 and intermediate products in process (I)

The subject of this invention is a new process with variant embodiments for the production of compound 1.