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

Description

Ethynyl Estradiol 3-Acetate is a synthetic steroid that is structurally similar to the naturally occurring female sex hormone, estradiol. It is known for its potent estrogenic activity and is commonly used in the pharmaceutical industry for various applications due to its effectiveness and stability.

Uses

Used in Pharmaceutical Industry:
Ethynyl Estradiol 3-Acetate is used as an active pharmaceutical ingredient for the development of oral contraceptives. It helps in regulating the hormonal balance in women, preventing ovulation, and thus serving as an effective birth control method.
Used in Hormone Replacement Therapy:
In addition to its use in oral contraceptives, Ethynyl Estradiol 3-Acetate is also utilized as a component in hormone replacement therapy (HRT) for menopausal women. It helps alleviate symptoms associated with menopause, such as hot flashes and night sweats, by providing the necessary estrogen levels.
Chemical Properties:
Ethynyl Estradiol 3-Acetate is a white solid with stable chemical properties, making it suitable for formulation and storage in various pharmaceutical products. Its solid form ensures ease of handling and processing during manufacturing and distribution.

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

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

Downstream Products

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