5779-47-5

Basic information

• Product Name: Ethynyl Estradiol 3-Acetate
• Synonyms: Ethynyl Estradiol 3-Acetate;(17α)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol 3-Acetate;19-Nor-17α-pregna-1,3,5(10)-trien-20-yne-3,17-diol 3-Acetate
• CAS NO: 5779-47-5
• Molecular Formula: C₂₂H₂₆O₃
• Molecular Weight: 338.44004
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Steroids
• Mol File: 5779-47-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 468.3°C at 760 mmHg
• Flash Point: 186.8°C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 1.42E-09mmHg at 25°C
• Refractive Index: 1.593
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: Ethynyl Estradiol 3-Acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethynyl Estradiol 3-Acetate(5779-47-5)
• EPA Substance Registry System: Ethynyl Estradiol 3-Acetate(5779-47-5)

Safety Data

• Hazardous Substances Data: 5779-47-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Ethynyl Estradiol 3-Acetate is used as a synthetic steroid with potential use as an oral contraceptive.

InChI:InChI=1/C22H26O3/c1-4-22(24)12-10-20-19-7-5-15-13-16(25-14(2)23)6-8-17(15)18(19)9-11-21(20,22)3/h1,6,8,13,18-20,24H,5,7,9-12H2,2-3H3/t18-,19-,20+,21+,22+/m1/s1

Upstream product

• 39845-30-2 3-(tert-butyldimethylsilyloxy)-17α-ethynyl-β-estradiol 
• 346700-38-7 3-(tert-butyldimethylsilyloxy)-17α-trimethylsilylethynyl-β-estradiol 
• 53-16-7 Estrone 
• 57-63-6 ethinyl estradiol 
• 108-24-7 acetic anhydride 

Downstream Products

• 586388-00-3 17α-20E-21-phenyl-19-norpregna-1,3,5(10),20-tetraene-3,17β-diol 3-acetate 
• 1363905-72-9 (17α,20E)-21-[3,4-dimethylphenyl]-19-norpregna-1,3,5(10),20-tetraene-3,17β-diol 
• 1363905-69-4 (17α,20E)-21-[2,6-dimethylphenyl]-19-norpregna-1,3,5(10),20-tetraene-3,17β-diol 
• 1380442-25-0 C₃₀H₃₆O₃ 
• 1380442-14-7 C₂₉H₃₄O₃ 
• 1363905-65-0 (17α,20E)-21-[2,4-dimethylphenyl]-19-norpregna-1,3,5(10),20-tetraene-3,17β-diol 
• 1380442-12-5 C₃₀H₃₆O₃ 
• 135643-29-7 17α-(4'-phenylbuta-1',3'-diynyl)estradiol 
• 108561-04-2 (17α,20E)-21-(phenylseleno)-19-norpregna-1,3,5(10),20-tetraene-3,17-diol 

Relevant articles and documents

Structure-Activity Relationships of Estrogenic Ligands: Synthesis and Evaluation of (17α,20E)- and (17α,20Z)-21-Halo-19-norpregna-1,3,5(10),20-tetraene-3,17β-diols

As part our program to probe the molecular requirement for estrogen-receptor binding we undertook the synthesis and evaluation of the 17α,E and 17α,Z halovinyl estradiols.By use of an improved variation of the existing synthetic strategy, the targeted compounds were prepared stereospecifically and in 92-98percent yields from the corresponding 17α,E or 17α,Z estradiol 3-acetates.The novel estradiol derivatives were evaluated for their relative binding affinity (RBA) for the estrogen receptor with use of a rat uterine preparation.The results demonstrated a marked difference between the E and Z isomers and among the halogen employed.The Z isomers possessed significantly higher RBA values and the larger halogens (I, Br) were more effective than the smaller Cl substituent.These results modify the previous interpretations of estrogen-receptor binding for steroidal ligands.As a result, our design of (radio)halogenated ligands will incorporate this concern for Z vs E stereochemistry.

ESTRADIOL-RELATED COMPOUNDS AND METHODS OF USE AS ANTI-TUMOR AGENTS

This invention relates to new estradiol-related compounds that can be used to treat various types of cancer including prostate and breast cancers.

HYPERVALENT IODINE OXIDATION OF ETHYNYLCARBINOLS: A SHORT AND EFFICIENT CONVERSION OF DIHYDROXYACETONYL GROUPS FROM KETO GROUPS

Oxidation of ethynylcarbinols (4a-g), prepared easily from ketones, with a hypervalent iodine reagent, phenyliodosyl bis(trifluoroacetate) (PIFA), in chloroform-acetonitrile-water gave the dihydroxyacetonyl compounds (6a-g) in high yields.Keywords: phenyliodosyl bis(trifluoroacetate); ethynylcarbinol; dihydroxyacetone; terminal alkyne; α-hydroxyketone