510-64-5

Basic information

• Product Name: 19-HYDROXY-4-ANDROSTENE-3,17-DIONE
• Synonyms: Androst-4-ene-3,17-dione, 19-hydroxy-;19-HYDROXY-4-ANDROSTEN-3,17-DIONE;19-HYDROXY-4-ANDROSTENE-3,17-DIONE;19-HYDROXYANDROSTENDIONE;19-HYDROXYANDROSTENEDIONE;4-ANDROSTENE-3,17-DIONE-19-0L;4-ANDROSTENE-3,17-DIONE-19-OL;4-ANDROSTEN-19-OL-3,17-DIONE
• CAS NO: 510-64-5
• Molecular Formula: C₁₉H₂₆O₃
• Molecular Weight: 302.41
• EINECS: 208-116-5
• Product Categories: All Inhibitors;Inhibitors;Steroids
• Mol File: 510-64-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 168-169 °C(lit.)
• Boiling Point: 485.4 °C at 760 mmHg
• Flash Point: 261.5 °C
• Appearance: off-white solid
• Density: 1.19 g/cm³
• Vapor Pressure: 1.84E-11mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.90±0.10(Predicted)
• BRN: 2567249
• CAS DataBase Reference: 19-HYDROXY-4-ANDROSTENE-3,17-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 19-HYDROXY-4-ANDROSTENE-3,17-DIONE(510-64-5)
• EPA Substance Registry System: 19-HYDROXY-4-ANDROSTENE-3,17-DIONE(510-64-5)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-63
• Safety Statements: 22-24/25-36/37/39-27-26-36/37
• WGK Germany: 3
• Hazardous Substances Data: 510-64-5(Hazardous Substances Data)

Usage

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 510-64-5 differently. You can refer to the following data:
1. A novel substituted estrogen as aromatase inhibitor
2. 19-Hydroxyandrostendione is a novel substituted estrogen as aromatase inhibitor. It induces neuroendocrine trans-differentiation of prostate cancer cells via an ectopic olactory receptor.

Purification Methods

Recrystallise 19-hydroxy-4-androsten-3,17-dione from Me2CO/hexane or Et2O/hexane. It has UV with max at 242nm in EtOH or MeOH. The 19-acetoxy derivative has [] 26D +185o (CHCl3) and max 237.5nm in EtOH. [Ehrenstein & Dünnenberger J Org Chem 21 774 1956, Beilstein 8 IV2162.]

InChI:InChI=1/C19H26O3/c1-18-8-7-16-14(15(18)4-5-17(18)22)3-2-12-10-13(21)6-9-19(12,16)11-20/h10,14-16,20H,2-9,11H2,1H3/t14-,15-,16-,18-,19+/m0/s1

Upstream product

• 510-65-6 19-hydroxycortodoxone 
• 33065-72-4 5β-androstane-3β,5,17β,19-tetraol 
• 79-15-2 N-bromoacetamide 
• 63-05-8 Androstenedione 
• 640-87-9 cortexolone 21-acetate 
• 19357-45-0 17α,21-dihydroxy-4-pregnene-3,20-dione 17-acetate 
• 152-58-9 Cortexolone 
• 104597-49-1 3-acetoxy-androst-5-en-17-one 
• 25375-38-6 3-hydroxy-5-androsten-17-one 
• 4968-05-2 androstane-3,5-dien-17-one-3β-ol acetate 
• 4777-63-3 3α,5-Cyclo-6β,19-epoxy-5α-androstan-17-on 
• 7677-64-7 19-oxo-5-androstene-3β,17β-diol 
• 115604-26-7 3β,5,19-triacetoxy-5β-pregnan-20-one 
• 20517-91-3 5-bromo-6β,19-epoxy-5α-androstane-3β,17β-diol 3-acetate 

Downstream Products

• 54201-89-7 19-(Triphenylsiloxy)-4-androstene-3,17-dione 
• 59877-74-6 ((8R,9S,10S,13S,14S)-13-methyl-3,17-dioxo-1,2,3,6,7,8,9,11,12,13,14,15,16,17-tetradecahydro-10H-cyclopenta[a]phenanthren-10-yl)methyl 4-methylbenzenesulfonate 
• 54201-84-2 C₂₄H₃₄O₅ 
• 68-22-4 norethisterone 
• 2863-88-9 3-ethoxy-19-nor-3,5-androstadiene-17-one 
• 17253-36-0 3-O-methyl-estra-1,3,5⁽¹⁰⁾,6-tetraen-17-one 
• 6639-99-2 17α-dihydroequilenin 
• 1423-97-8 17β-dihydroequilenin 
• 517-09-9 equilenin 
• 3907-67-3 3-O-methylequilinine 
• 1229-32-9 d-Isoequilenin methylether 
• 33760-56-4 14-dehydro-17β-dihydroequilenin-3-methylether 
• 56614-59-6 14-dehydroequilenin-3-methylether 
• 1624-62-0 estrone 3-methyl ether 

Relevant articles and documents

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Kinetic solvent isotope effect in steady-state turnover by CYP19A1 suggests involvement of Compound 1 for both hydroxylation and aromatization steps

CYP19A1, or human aromatase catalyzes the conversion of androgens to estrogens in a three-step reaction through the formation of 19-hydroxy and 19-aldehyde intermediates. While the first two steps of hydroxylation are thought to proceed through a high-valent iron-oxo species, controversy exists surrounding the identity of the reaction intermediate that catalyzes the lyase and aromatization reaction. We investigated the kinetic isotope effect on the steady-state turnover of Nanodisc-incorporated human CYP19A1 to explore the mechanisms of this reaction. Our experiments reveal a significant (～2.5) kinetic solvent isotope effect for the C10-C19 lyase reaction, similar to that of the first two hydroxylation steps (2.7 and 1.2). These data implicate the involvement of Compound 1 as a reactive intermediate in the final aromatization step of CYP19A1.

19 Hydroxylated cortisone derivative and preparation method 19 - hydroxyl androstenedione (by machine translation)

The invention discloses 19 hydroxylated cortisone derivatives and a preparation method, namely 19 - hydroxyandrostenedione. Belong to organic synthesis and pharmacy field. To the invention, 19 - hydroxyl group can be used as a raw material, 19 - hydroxyl can be supported in a plurality of groups under the action of hydrogen peroxide, trimethyl iodosilane, palladium carbon, dichloro dicyanobenzene quinone, iodobenzene, sodium borohydride, sodium periodate and the like respectively. 19 - hydroxyl can be supported to 19 - respectively. B ring can be supported by structural modification 17. 21 And/or 19-position hydroxyl groups are substituted; cleavage 19 - hydroxyl groups may support many loose side chains. The preparation method of the essential intermediate 19 - hydroxyandrostenedione synthesized by the norethindrone contraceptive is greatly improved, and the drug production cost. (by machine translation)

Preparation method of 19-demethylation-4-androstenedione

The invention discloses a preparation method of 19-demethylation-4-androstenedione and belongs to the technical field of medical intermediate processing. The preparation method comprises the following steps: (1) carrying out esterification reaction; (2) carrying out ketalation; (3) carrying out reduction reaction; (4) carrying out hydrolysis reaction; (5) carrying out esterification reaction; (6) carrying out addition reaction; (7) carrying out cyclization and hydrolysis reaction; (8) carrying out oxidation, dechloridation and ring-opening reaction; and (9) carrying out oxidation and decarboxylation reaction. The preparation method disclosed by the invention has the advantages that environmental pollution is small, usage amounts of a solvent and water are smaller, temperature sensitivity is low, control is easy, and yield is high; a chlorinating agent is adopted, so that reaction yield is increased; 1,3-dichloro-5,5-dimethylhydantoin is adopted, so that the reaction yield is further increased; and sodium hydrogen carbonate is adopted, so that final decarboxylic reaction yield is increased, and external standards and appearance of a product can be improved.