1743-60-8

Usage

Uses

Used in Pharmaceutical Industry:
BETA-ESTRADIOL 17-ACETATE is used as a hormone replacement therapy (HRT) for various conditions related to menopause, such as hot flashes, night sweats, and vaginal atrophy. It helps in maintaining bone density and reducing the risk of osteoporosis.
Used in Environmental Protection:
BETA-ESTRADIOL 17-ACETATE is listed as a drinking water contaminant candidate (CCL 3) by the United States Environmental Protection Agency (EPA). This indicates its potential presence in the environment and the need for monitoring and controlling its levels to ensure public health and safety.
Used in Research and Development:
BETA-ESTRADIOL 17-ACETATE is used in body burden analyses to study the effects of various environmental contaminants, such as triclosan, on aquatic organisms like estuarine fish. This helps in understanding the impact of these contaminants on the ecosystem and developing strategies for their mitigation.
Used in Medical Devices:
BETA-ESTRADIOL 17-ACETATE is used in the development of medical devices, such as vaginal rings, for the treatment of menopausal symptoms. The brand names Femring (Galen) and Femtrace (Warner Chilcott) are examples of such devices that utilize BETA-ESTRADIOL 17-ACETATE for its hormone replacement properties.

Biochem/physiol Actions

β-Estradiol is a steroid hormone involved in a number of organ functions. It is significantly associated with brain functions including neuroprotection, neurogenesis and synaptic plasticity. β-Estradiol maintains bone homeostasis, and hence is preferred for osteoporosis therapy. 17-β-Estradiol is the most active estrogen generated in our body. During postmenopausal, 17-β-estradiol inhibits oxidative modification in low density lipoprotein. This indicates that estrogen replacement therapy might be useful in treating cardiovascular disease.

InChI:InChI=1/C20H26O3/c1-12(21)23-19-8-7-18-17-5-3-13-11-14(22)4-6-15(13)16(17)9-10-20(18,19)2/h4,6,11,16-19,22H,3,5,7-10H2,1-2H3

Upstream product

• 50-28-2 estradiol 
• 1474-52-8 estradiol-3,17-diacetate 
• 88378-62-5 estra-1,3,5(10),6-tetraene-3,17-diol, 17-acetate, (17β)- 
• 23880-55-9 17β-Acetoxy-3-benzyloxyestra-1,3,5(10)-triene 
• 64-19-7 acetic acid 
• 14982-15-1 3-benzyloxyestra-1,3,5(10)-trien-17β-ol 
• 108-24-7 acetic anhydride 
• 50-28-2 estradiol 
• 60759-49-1 N-acetyl-1,3-oxazol-2-one 
• 1425-10-1 19-nortestosterone acetate 
• 13731-44-7 3-Oxo-4β,5β-oxido-17β-acetoxy-oestran 
• 1164-99-4 17β-acetoxy-4-chloro-estr-4-en-3-one 
• 4954-14-7 (8R,9S,13S,14S,17S)-3,17-dimethoxy-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene 
• 53512-67-7 2β-Fluor-17-acetoxyestr-5(10)-en-3-on 

Downstream Products

• 4954-17-0 benzoate of 17β-acetylestradiol 
• 105546-99-4 17β-Acetoxy-3-sulfooxyestra-1,3,5(10)-triene triethylammonium salt 
• 50-28-2 estradiol 
• 96070-59-6 17β-acetoxy-3-(2,4-dinitro-phenylazo)-estra-1,3,5(10)-triene 
• 59495-70-4 methyl {(17β-acetoxy-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate 
• 15270-30-1 estradiol 3-O-glucuronide 
• 88847-87-4 2-chloroestradiol 
• 549-02-0 10β,17β-dihydroxyestra-1,4-dien-3-one 
• 4147-11-9 10-acetoxy-17β-hydroxy-estra-1,4-dien-3-one 
• 102953-57-1 17β-benzoyloxy-5α,10α-estran-3-one 
• 144082-87-1 C₂₀H₂₄O₄ 
• 144082-89-3 C₂₀H₂₄O₄ 
• 41164-36-7 2-<(17β-Hydroxyestra-1,3,5(10)-trien-3-yl)oxy>acetic Acid 
• 31299-96-4 estradiol-17β 3-β-D-glucopyranoside 

Relevant academic research and scientific papers

DEACYLATION OF AROMATIC ACETATES. A NEW METHOD OF SELECTIVE PROTECTION OF THE HYDROXYL FUNCTION.

Acetoxyaromatic compounds are selectively deacylated, via a catalytic-type reaction, to the corresponding phenolic derivatives, by treatment with activated zinc in methanol.

Synthesis and Characterization of Hybrid Dimeric Steroid Spiroketals

The synthesis of six dimeric spiroketals bearing an estradiol half fused to the 5α- or 5β-epimers of androstane, cholestane, and spirostane nuclei is described. The synthetic procedure comprises the Sonogashira coupling of different steroid alkynes with 2-iodoestradiol 17-monoacetate, followed by Pd-catalyzed spiroketalization. The structural characterization of the obtained hybrid dimers was performed using a combination of 1D and 2D NMR techniques, and was assisted by DFT calculations. Single crystal X-ray diffraction of one of the obtained compounds confirmed the proposed structures.

Samarium(II) dibromide-promoted selective deprotection of a benzoyl protective group

The selective deprotection of a benzoyl group was very important methodology in the field of organic synthesis. Various methods for debenzoylation were investigated and developed in the past six decades, but more useful and selective strategies are now being strongly desired. In response to this strong demand, we developed the novel and selective deprotection of a benzoyl group by use of samarium(II) dibromide and a proton source. This deprotective reaction proceeded smoothly and the desired compound was obtained in good to excellent yields. In this paper, we will report the details of this deprotective reaction.

Efficient and selective N-, S- and O-acetylation in TEAA ionic liquid as green solvent. Applications in synthetic carbohydrate chemistry

Background: The ionic liquid triethylammonium acetate (TEAA) was found to be an efficient solvent in the acetylation of alcohols, amines, oximes and thiols to their corresponding acetyl compounds using only a 10% excess of acetic anhydride under mild conditions. Moreover TEAA is not only an inexpensive and recyclable solvent but also an anomeric selective catalyst in the per-O-acetylation of sugar moieties. Methods: Simple and effective organic synthesis protocols were provided for the selective acetylation of several substrates. The products were fully characterized by 1H and 13C NMR spectroscopy and the anomeric ratios were obtained from the 1H spectra. Results: Structurally diverse alcohols, phenols, thiols, amines, carbohydrates and oximes underwent acylation under mild conditions by this procedure to provide the corresponding acetates in excellent yields. TEAA ionic liquid is unique in its capability to act as both, solvent and high selective catalyst. As expected, the reaction proceeds with high b anomeric selectivity for sugars derivatives. Moreover, the ionic liquid was regenerated, recycled and reused for three times without apparent loss of reactivity and selectivity in all cases. Conclusions: The present procedure provides a powerful and versatile acylation method for alcohols, phenols, thiols, amines, oximes and carbohydrates. This protocol is endowed with several unique merits: selectivity, cost-efficiency, atom-economy and mild reaction conditions tolerable to acid sensitive functionalities. With these features, this method may be considered as a better alternative for the acetylation of a wide range of substrates.

Improved and scalable synthetic route to the synthon 17-β-(2- Carboxyethyl)-1,3,5(10)-estratriene: An important intermediate in the synthesis of bone-targeting estrogens

An improved, highly scalable methodology for the multigram-scale preparation of an important synthon, 17-β-(2-carboxyethyl)-1,3,5(10)- estratriene, is described. Previous approaches have failed to provide useful quantities of the analytically pure product because of facile retro-Michael breakdown of the-alkoxy carbonyl precursors during workup and isolation operations. The synthetic approach described herein has been designed specifically to sidestep this problematic breakdown process. This new scalable method of preparation overcomes a major hurdle in the exploration of structure-activity relationships centered around novel estradiol derivatives with bone-targeting properties and also provides a scalable process for subsequent developmental work.

PROCESS FOR AROMATIZING 19-NORANDROST-4-EN-3-ONES TO ESTRA-1,3,5(10)-TRIENES

The present invention relates to a process for aromatizing 19-norandrost-4-en-3-ones (formula (II)) to astra-1,3,5(10)-trienes (formula (I))

A simple, general, and highly chemoselective acetylation of alcohols using ethyl acetate as the acetyl donor catalyzed by a tetranuclear zinc cluster

In the presence of a Zn-cluster catalyst, alcohols are efficiently converted to the corresponding acetate just by refluxing in EtOAc. The mild reaction conditions enabled the reactions of various functionalized alcohols to proceed in good to excellent yield. Moreover, even when a large excess of the acetyl donor is used, the hydroxyl groups are selectively acetylated in the presence of highly nucleophilic aliphatic amino groups, approaching chemoselectivity to that of enzymatic system. Georg Thieme Verlag Stuttgart.

A NEW PROCESS FOR THE PREPARATION OF PHENOLIC HYDROXY-SUBSTITUTED COMPOUNDS

The invention relates to a process for the preparation of a phenolic hydroxy-substituted compound of the general formula (I) by desalkylation of an alkyl aryl ether of the general formula (II) by treatment with a thiourea/aluminium chloride reagent pair, in said general formulae R1 stands for straight chain or branched C1-6 alkyl group; R2, R3, R4, R5 , and R6 have the same or different meanings and stand for hydrogen or halogen atom, hydroxy, carboxy, nitro, oxo, C1-6 alkylcarbonyl, straight chain or branched alkyl or - alkoxy, or aryl group, or R2 and R3 together stand for a 5-7 membered ring or fused ring system; said 5-7 membered ring may be a partially saturated ring optionally substituted with an oxo group or can be an unsaturated ring; or said fused ring system may constitute with the first ring a steroid, preferably an estratriene derivative optionally substituted with an oxo or C1-6 alkylcarbonyloxy group in the 17 position -.

A novel and convenient chemoselective deprotection method for both silyl and acetyl groups on acidic hydroxyl groups such as phenol and carboxylic acid by using a nitrogen organic base, 1,1,3,3-tetramethylguanidine

(Matrix presented) 1,1,3,3-Tetramethylguanidine (TMG)1, a nitrogen organic base, is a convenient and useful reagent for chemoselective deprotection of both silyl and acetyl groups on acidic hydroxyl groups such as phenol and carboxylic acid without affecting aliphatic silyl and acetyl groups. The chemoselectivity is dependent on the acidity of the hydroxyl group.

Lipase-catalysed chemoselective monoacetylation of hydroxyalkylphenols and chemoselective removal of a single acetyl group from their diacetates

It was demonstrated that Pseudomonas cepacia PS lipase adsorbed on Celite, has the ability to catalyse the chemoselective monoacetylation of various hydroxyalkylphenols or the chemoselective removal of a single acetyl group from the corresponding acetate.