2393-53-5

Basic information

• Product Name: 3-Hydroxyestra-1,3,5(10)-trien-17-one benzoate
• Synonyms: 3-Hydroxyestra-1,3,5(10)-trien-17-one benzoate;OESTRONEBENZOATE;(13-methyl-17-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl) benzoate;benzoic acid (17-keto-13-methyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-yl) ester
• CAS NO: 2393-53-5
• Molecular Formula: C₂₅H₂₆O₃
• Molecular Weight: 374.51
• Product Categories: Steroids
• Mol File: 2393-53-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 217-220 °C
• Boiling Point: 463.47°C (rough estimate)
• Flash Point: 230.4°C
• Appearance: /
• Density: 1.0636 (rough estimate)
• Vapor Pressure: 2.52E-11mmHg at 25°C
• Refractive Index: 1.5460 (estimate)
• CAS DataBase Reference: 3-Hydroxyestra-1,3,5(10)-trien-17-one benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxyestra-1,3,5(10)-trien-17-one benzoate(2393-53-5)
• EPA Substance Registry System: 3-Hydroxyestra-1,3,5(10)-trien-17-one benzoate(2393-53-5)

Safety Data

• Hazardous Substances Data: 2393-53-5(Hazardous Substances Data)

Usage

Safety Profile

Suspected carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. Other experimental reproductive effects. Mutation data reported. A steroid drug for the treatment of menopause. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C25H26O3/c1-25-14-13-20-19-10-8-18(28-24(27)16-5-3-2-4-6-16)15-17(19)7-9-21(20)22(25)11-12-23(25)26/h2-6,8,10,15,20-22H,7,9,11-14H2,1H3

Upstream product

• 53-16-7 Estrone 
• 10533-83-2 N-benzoyl-N-methyl-4-methylbenzenesulfonamide 
• 53-16-7 rac-3-hydroxy-(8α)-estra-1,3,5(10)-trien-17-one 
• 98-88-4 benzoyl chloride 
• 19973-76-3 (+/-)-oestrone 
• 53-16-7 rac-3-hydroxy-(9β,13α)-estra-1,3,5(10)-trien-17-one 
• 85909-02-0 N-benzyl-N-(tert-butoxycarbonyl)-benzamide 
• 50-27-1 Estriol 

Downstream Products

• 94618-89-0 benzoyloxy-3 N-oxy methylimino-17 estra-1,3,5 ⁽¹⁰⁾ triene nitrone 
• 4954-17-0 benzoate of 17β-acetylestradiol 
• 15183-37-6 15α-hydroxyestriol 

Relevant articles and documents

Synthesis of 14?-cyanomethyl derivatives of estradiol and the estimation of their antineoplastic activity in vitro

14?-Cyanomethyl derivatives of estrone and estradiol have been synthesized starting from 3-benzoyloxyestra-1,3,5(10),14,16-pentaen-17-yl acetate. A comparative study of their cytotoxicity in breast carcinoma ZR-75-1, cervix uteri carcinoma M-HeLa, uterus

Photo-Fries Rearrangement of Some 3-Acylestrones in Homogeneous Media: Preparative and Mechanistic Studies

Irradiation of a series of 3-acylestrones under a nitrogen atmosphere in cyclohexane, acetonitrile (MeCN), and methanol (MeOH) was investigated under steady-state conditions. The molecules underwent the photo-Fries rearrangement, with concomitant homolytic fragmentation of the ester group and [1;3]-acyl migration. This pathway afforded the ortho-acyl estrone derivatives, the main photoproducts, together with estrone. During the irradiation of 3-benzoyl estrone, epimerization of estrone through the Norrish type I reaction occurred, providing lumiestrone as the photoproduct. This photoreaction involves the fragmentation of the C-α at the carbonyl group (C-17) of the steroid. On the other hand, epimerization of ortho-regioisomer 2-acetyl estrone occurred during the irradiation of 3-acetyl estrone. Photosensitization with acetone and chemical quenching with N,N,N,N-tetramethyldiazetinedioxide of the photo-Fries reaction confirmed that the photoreaction took place from the singlet excited state while the Norrish type I reaction proceeds efficiently from the triplet excited state. Solvent effects, as well as the nature of the acyl group on the photoreactions, were also studied.

PROCESS FOR THE PREPARATION OF ESTETROL

The invention relates to a process for obtaining Estetrol or a salt or solvate thereof, the process comprising: a) reacting a compound of formula (IV) or a salt or solvate thereof, wherein R1 is a hydroxyl protecting group selected from a silyl ether, an ether, an ester, a carbamate and a carbonate, and R2 is a hydroxyl protecting group selected from an ether, with an oxidizing agent selected from OsO4 or a source of osmium tetroxide to produce Estetrol or a compound of formula (II) or a salt or solvate thereof wherein R1 is as defined previously; and b) if a compound of formula (II) is obtained in step a), deprotecting said compound to produce Estetrol.