4999-76-2

Basic information

• Product Name: 3,17β-Diacetoxy-3,5-estradiene
• Synonyms: (17β)-Estra-3,5-diene-3,17-diol 3,17-Diacetate;(17β)-Estra-3,5-diene-3,17-diol Diacetate;3,17β-Diacetoxy-3,5-estradiene;GAIRDOKUNQTVPZ-ZCPXKWAGSA-N
• CAS NO: 4999-76-2
• Molecular Formula: C₂₂H₃₀O₄
• Molecular Weight: 358.4712
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 4999-76-2.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3,17β-Diacetoxy-3,5-estradiene(CAS DataBase Reference)
• NIST Chemistry Reference: 3,17β-Diacetoxy-3,5-estradiene(4999-76-2)
• EPA Substance Registry System: 3,17β-Diacetoxy-3,5-estradiene(4999-76-2)

Safety Data

• Hazardous Substances Data: 4999-76-2(Hazardous Substances Data)

Usage

Description

3,17β-Diacetoxy-3,5-estradiene is an organic compound that belongs to the class of steroids. It is a white solid with specific chemical properties that make it suitable for various applications, particularly in the pharmaceutical and chemical industries.

Uses

Used in Pharmaceutical Industry:
3,17β-Diacetoxy-3,5-estradiene is used as an intermediate compound for the synthesis of various steroidal drugs. Its chemical structure allows for the modification and creation of a wide range of steroidal medications, including hormones, anti-inflammatory drugs, and contraceptives.
Used in Chemical Industry:
In the chemical industry, 3,17β-Diacetoxy-3,5-estradiene serves as a key building block for the production of other steroidal compounds. Its versatility in chemical reactions enables the synthesis of various complex steroidal molecules with specific applications in different fields.
Used in Research and Development:
3,17β-Diacetoxy-3,5-estradiene is also utilized in research and development for the study of steroidal compounds and their biological effects. Its unique structure provides valuable insights into the design and development of new drugs and pharmaceuticals with improved efficacy and safety profiles.

Upstream product

• 434-22-0 19-nortestosterone 
• 108-24-7 acetic anhydride 
• 75-36-5 acetyl chloride 
• 108-22-5 Isopropenyl acetate 
• 1091-93-6 3-methoxy-17-hydroxyestra-2,5⁽¹⁰⁾-diene 
• 108-21-4 Isopropyl acetate 

Downstream Products

• 2590-41-2 6-dehydro-19-nortestosterone acetate 
• 25975-59-1 3β,17β-dihydroxy-19-norandrost-5-ene 
• 3801-28-3 17β-acetoxy-6α-fluoro-4-estren-3-one 
• 18119-95-4 17β-acetoxy-6β-fluoro-4-estren-3-one 
• 1425-10-1 19-nortestosterone acetate 
• 6599-92-4 17β-acetoxy-3-hydroxy-1,3,5(10)-estratriene-6-one 
• 3434-45-5 6-oxo-3,17β-estradiol diacetate 
• 115759-24-5 (3S)-3,17β-bis-(3,5-dinitro-benzoyloxy)-9,10-seco-estra-5(10),6t,8-triene 
• 6157-87-5 7alpha-Methyl-19-nortestosterone acetate 
• 54793-00-9 17β-hydroxy-7α-methyl-estr-5-en-3-one acetate 
• 3764-87-2 7α-methyl-19-nortestosterone 
• 153004-31-0 (+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol 
• 129453-61-8 fulvestrant 
• 875573-69-6 17-O-acetyl-S-deoxo-fulvestrant 

Relevant articles and documents

BILE ACIDS AND STEROIDS. 28. THIOSTEROIDS. 13. FURTHER STUDY ON

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Preparation method for 3,5-estradiene-3,17beta-diacetate

The invention relates to a preparation method for 3,5-estradiene-3,17beta-diacetate. The preparation method comprises the following steps: sequentially adding nandrolone, p-toluenesulfonic acid monohydrate, isopropyl acetate and magneton No. 15 into a reactor, introducing condensed water, carrying out a heating reaction in an oil-bath pot and slowing adding isopropenyl acetate when reflux condensation of the obtained system begins; after completion of a reaction, carrying out evaporation to remove a solvent; cooling the system, adding pyridine, and adding isopropanol drop by drop until a white solid product is precipitated; carrying out low-temperature cooling and pumping filtration and then carrying out cleaning with cold isopropanol; collecting the white solid product and then carrying out drying so as to obtain a pure 3,5-estradiene-3,17beta-diacetate product. According to the invention, nandrolone is used as a substrate and a one-pot method is employed for carbonyl and hydroxyl acetylation protection so as to synthesize the product; the method is simple in process, mild in conditions and friendly to environment and has yield of up to 85%; and the synthesized product has critical application value in the fields of medicines, veterinary drugs and pesticides and is an important pro-drug for tibolone.

Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803

A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe3 reacted with four steroid dienone precursors to afford either the corresponding α-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of α/β was up to 10/1. No β-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15β-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7α and C-15β positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803.