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

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

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.

Triazole-estradiol analogs: A potential cancer therapeutic targeting ovarian and colorectal cancer

1,2,3-triazoles have continuously shown effectiveness as biologically active systems towards various cancers, and when used in combination with steroid skeletons as a carrier, which can act as a drug delivery system, allows for a creation of a novel set of analogs that may be useful as a pharmacophore leading to a potential treatment option for cancer. A common molecular target for cancer inhibition is that of the Epidermal Growth Factor Receptor/Mitogen Activated Protein Kinase pathways, as inhibition of these proteins is associated with a decrease in cell viability. Estradiol-Triazole analogs were thus designed using a molecular modeling approach. Thirteen of the high scoring analogs were then synthesized and tested in-vitro on an ovarian cancer cell line (A2780) and colorectal cancer cell line (HT-29). The most active compound, Fz25, shows low micromolar activity in both the ovarian (15.29 ± 2.19 μM) and colorectal lines (15.98 ± 0.39 μM). Mechanism of action studies proved that Fz25 moderately arrests cells in the G1 phase of the cell cycle, specifically inhibiting STAT3 in both cell lines. Additionally, Fz57 shows activity in the colorectal line (24.19 ± 1.37 μM). Inhibition studies in both cell lines show inhibition against various proteins in the EGFR pathway, namely EGFR, STAT3, ERK, and mTOR. To further study their effects as therapeutics, Fz25 and Fz57 were studied against drug efflux proteins, which are associated with drug resistance, and were found to inhibit the ABC transporter P-glycoprotein. We can conclude that these estradiol-triazole analogs provide a key for future studies targeting protein inhibition and drug resistance in cancer.

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.

17α -Substituted analogs of estradiol for the development of fluorescent estrogen receptor ligands

For the successful development of a high-affinity fluorophore-estradiol conjugate, the fluorophore must be attached to the estradiol molecule at a position that interferes least with its binding to the receptor. We have concentrated on 17α. substituents as models for fluorophore attachment, based on literature precedent and on our earlier work with small 17α. side chains. In this report, we describe syntheses and estrogen receptor binding affinities of 19 analogs of estradiol substituted in the 17α position with larger side chains (of six to 11 carbons), some of which may be synthetically modified to link a fluorophore. These analogs were synthesized either by nucleophilic cleavage of estrone-17β-oxirane 3-benzyl ether and subsequent debenzylation (4 to 18), by cross-coupling of alkynes (21 to 24), by alkylation of 17 αethynylestradiol 3,17-bis(tetrahydropyranyl ether) and subsequent acidic hydrolysis (25 to 28), or by reacting estrone either with appropriate aryllalkynyllithium reagents (29,30, and 32) or with benzylmagnesium bromide (31). Relative binding affinities of these newly synthesized analogs were determined for estrogen receptor (rat uterus) using a standard competition assay. The results suggest that analogs with reduced mobility and/or more polarizable electron density in the side chain generally bind more strongly to the receptor. The relative affinities of several selected compounds were also determined in the presence of 4% dimethylformamide; some compounds bearing larger, nonpolar 17α. substituents showed dramatically improved affinities, while affinities for compounds with shorter nonpolar side chains remained largely unchanged. These binding affinity results should be useful in designing new high-affinity fluorescent ligands for the estrogen receptor.

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

17β-Ethynyl-3,17α-estradiol and derivatives thereof

17β-ethynyl-3,17α-estradiol and derivatives thereof are prepared by epimerization of 17-acyl esters of 17α-ethynyl-3,17β-estradiol 3-ethers. 17α-ethynyl-3,17α-estradiol and its derivatives are active as post-coital antifertility agents and inhibit the growth of or reduce the size of the prostate gland and the seminal vesicle.

17β-Ethynyl-3,17α-estradiol and derivatives thereof

17β-ethynyl-3,17α-estradiol and derivatives thereof are prepared by epimerization of 17-acyl esters of 17α-ethynyl-3,17β-estradiol 3-ethers. 17β-ethynyl-3,17αestradiol and its derivatives are active as post-coital antifertility agents and inhibit the growth of or reduce the size of the prostate gland and the seminal vesicle.