1159-66-6

Basic information

• Product Name: (3S,8R,9S,10R,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one
• Synonyms: (3S,8R,9S,10R,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one;16-Oxoandrostenediol;3 beta,17 beta-dihydroxyandrost-5-en-16-one;5-Androstene-3B,17B-diol-16-one;5-Androstene-3beta,17beta-diol-16-one
• CAS NO: 1159-66-6
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.42
• Mol File: 1159-66-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 469.6°Cat760mmHg
• Flash Point: 251.9°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 5.86E-10mmHg at 25°C
• Refractive Index: 1.576
• CAS DataBase Reference: (3S,8R,9S,10R,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one(CAS DataBase Reference)
• NIST Chemistry Reference: (3S,8R,9S,10R,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one(1159-66-6)
• EPA Substance Registry System: (3S,8R,9S,10R,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one(1159-66-6)

Safety Data

• Hazardous Substances Data: 1159-66-6(Hazardous Substances Data)

Usage

General Description

The chemical "(3S,8R,9S,10R,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,7,8,9,11,12,14,15,17-dodecahydrocyclopenta[a]phenanthren-16-one" is a steroid compound with a cyclopenta[a]phenanthren structure. It contains two hydroxyl groups at positions 3 and 17, and two methyl groups at positions 10 and 13. The compound also contains a ketone group at position 16. It belongs to the class of androstane steroids, which are important for a variety of physiological functions in the body, including hormone regulation and cellular signaling. This particular compound may have potential biological activities and could be of interest for medicinal or research purposes.

InChI:InChI=1/C19H28O3/c1-18-6-5-15-14(16(18)8-13(21)10-18)4-3-11-7-12(20)9-17(22)19(11,15)2/h9,11,13-16,20-21H,3-8,10H2,1-2H3/t11?,13-,14-,15+,16+,18-,19+/m1/s1

Upstream product

• 1249-72-5 3β,17β-diacetoxy-androst-5-en-16-one 
• 1093-91-0 3β-hydroxy-16α-bromoandrost-5-ene-17-one 
• 53-43-0 dehydroepiandrosterone 
• 74644-60-3 16β-bromo-3β-hydroxy-5-androsten-17-one 
• 1232-73-1 16α-hydroxy dehydroepiandrosterone 
• 1122098-27-4 C₁₉H₂₇⁽²⁾HO₃ 
• 979-62-4 3β-acetoxy-5α,6β-dichloroandrostan-17-one 
• 17975-95-0 5α,6β-dichloroandrost-16-en-3β,17-diol diacetate 
• 18878-64-3 16-Acetyl-3β,16,17-triacetoxy-androsten-(5) 
• 18944-55-3 16-(1β-Hydroxy-aethyl)-3β,16α,17-trihydroxy-androsten-(5)-acetonid 
• 5297-31-4 1-(17-amino-3β-hydroxy-androsta-5,16-dien-16-yl)-ethanone 
• 378223-43-9 3β-acetoxy-16β-(acetoxy)acetoxyandrost-5-en-17-one 
• 18878-68-7 16-(1β-Hydroxy-ethyl)-3β,16α,17-trihydroxy-androsten-(5) 
• 10587-75-4 17-oxoandrost-5-ene-3β,16α-diyl diacetate 

Downstream Products

• 104921-07-5 3β,17β-Dihydroxy-5-androsten-16-one Phenylhydrazone 
• 2099-26-5 androstenediol-3,17-diacetate 
• 17980-97-1 3β-benzoyloxy-androst-5-en-16-one 
• 14072-21-0 3β-Hydroxy-5-androsteno-16,17-dione-17-phenylhydrazone-16-p-nitrophenylhydrazone 
• 14072-22-1 3β-Hydroxy-5-androsten-16,17-dione-16-p-nitrophenylhydrazone 
• 79884-22-3 16β-acetoxy-3β,17β-bis(tetrahydro-2-pyranyloxy)-15α-tolylsulfonyloxymethyl-5-androstene 
• 79884-27-8 3β,17β-bis(tetrahydro-2-pyranyloxy)-15α-tolylsulfonyloxy-5-androsten-16β-ol 
• 14474-06-7 5-androsten-3β,16β,17β-triol 
• 5088-64-2 3β-hydroxy-5-androsten-16-one 

Relevant articles and documents

Mechanistic aspects of rearrangement of 16α-hydroxy-17-keto steroids to the 17β-hydroxy-16-keto isomers

The mechanistic aspects of the alkali-catalyzed rearrangement of 16α-hydroxy-17-keto steroid 1 to 17β-hydroxy-16-keto steroid 2 are elucidated by use of 18O- and deuterium-labeling experiments. The 18O-labeling experiments refute the gem-hydration-quasi-diaxial dehydration mechanism for the rearrangement previously proposed and support the conventional enolization mechanism. Moreover, equilibrium by gem-hydration-dehydration occurs at the C-17 carbonyl more efficiently than at the C-16 carbonyl. Enolization rate of a carbonyl group at C-16 of 17β-ketol 2 toward the C-17 position (k16,17) was about 8-10 times higher than those of 16α-ketol 1 toward the C-16 position (k17,16) and ketol 2 toward the C-15 position (k16,15). The marked deuterium-isotope effect on each enolization was observed with kH/kD ranging between 5.4 and 8.8. The present findings reveal that the initial hydration-dehydration equilibration at the C-17 carbonyl of ketol 1 followed by enolization of the carbonyl gives the ene-diol intermediate that isomerizes quantitatively to the 16-keto isomer of which the 16-carbonyl moiety enolizes preferentially toward the C-17 position rather than the C-15 position, yielding the ene-diol. Computational calculations of ground state energies of ketols 1-M and 2-M, trans-cyclohexane/cyclopentane structures, and their activation energies in the rearrangement support the dynamic aspects of the rearrangement as well as the kinetics data of the enolization.

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C19-Steroids as androgen receptor modulators: Design, discovery, and structure-activity relationship of new steroidal androgen receptor antagonists

Dehydroepiandrosterone (DHEA), the most abundant steroid in human circulating blood, is metabolized to sex hormones and other C19-steroids. Our previous collaborative study demonstrated that androst-5-ene-3β,17β-diol (Adiol) and androst-4-ene-3,17-dione (Adione), metabolites of DHEA, can activate androgen receptor (AR) target genes. Adiol is maintained at a high concentration in prostate cancer tissue; even after androgen deprivation therapy and its androgen activity is not inhibited by the antiandrogens currently used to treat prostate cancer patients. We have synthesized possible metabolites of DHEA and several synthetic analogues and evaluated their role in androgen receptor transactivation to identify AR modulators. Steroids with low androgenic potential in PC-3 cell lines were evaluated for anti-dihydrotestosterone (DHT) and anti-Adiol activity. We discovered three potent antiandrogens: 3β-acetoxyandrosta-1,5-diene-17-one 17-ethylene ketal (ADEK), androsta-1,4-diene-3,17-dione 17-ethylene ketal (OAK), and 3β-hydroxyandrosta-5,16-diene (HAD) that antagonized the effects of DHT as well as of Adiol on the growth of LNCaP cells and on the expression of prostate-specific antigen (PSA). In vivo tests of these compounds will reveal their potential as potent antiandrogens for the treatment of prostate cancer.

Steroids, L. Ring D Cleavage of D-Trisubstituted Steroids

In alkaline medium, 3β,17β-dihydroxy-15-(hydroxymethylene)androst-5-en-16-one (2a) is cleaved in two ways to give D-seco compounds.Dilute bases in protic solvents cause 1,3-dicarbonyl splitting to the 15-formyl-15,16-seco-16-oic acid 3, while the use of sodium methanolate in benzene solution gives rise to 16,17-splitting to afford the 15-formyl-16,17-seco-16,17-dioic acid 5.Both seco compounds redily undergo lactolone ring closure to give 4a and 6a, respectively.The malonaldehyde moiety of 5 is transformed in two directions: either loss of the formyl group to give 3β-hydroxy-16,17-secoandrost-5-ene-16,17-dioic acid (7a) or decarboxylation to 3β-hydroxy-16-oxo-16,17-secoandrost-5-en-17-oic acid (9) is observed. Key Words: Steroids/ 15-Hydroxymethylene-16-ketosteroids/ D-seco-steroids/ D-Homo-oxa-steroids