53-63-4

Usage

Uses

Used in Pharmaceutical Industry:
17-desoxyestradiol is used as a pharmaceutical agent for its hormonal activity. It can be utilized in the development of drugs targeting hormonal imbalances and related conditions due to its structural similarity to estradiol and estrone.
Used in Research Applications:
In the field of research, 17-desoxyestradiol serves as an important tool for studying the mechanisms of steroid hormone action and their effects on various physiological processes. It aids scientists in understanding the role of hormones in health and disease.
Used in Hormone Replacement Therapy:
17-desoxyestradiol can be employed as a component in hormone replacement therapies, particularly for conditions that involve a deficiency or imbalance of sex hormones. Its ability to mimic the effects of estradiol and estrone makes it a potential candidate for such treatments.
Used in Cosmetic Industry:
Due to its hormonal properties, 17-desoxyestradiol may also find applications in the cosmetic industry for anti-aging and skin care products. It could potentially be used to develop formulations that promote skin health and address aging-related concerns.

InChI:InChI=1/C18H24O/c1-18-9-2-3-17(18)16-6-4-12-11-13(19)5-7-14(12)15(16)8-10-18/h5,7,11,15-17,19H,2-4,6,8-10H2,1H3/t15-,16-,17+,18+/m1/s1

Upstream product

• 53-16-7 Estrone 
• 75-77-4 chloro-trimethyl-silane 
• 14550-57-3 3-methoxy-1,3,5(10)-estratriene 
• 71-36-3 butan-1-ol 
• 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 
• 53-16-7 rac-3-hydroxy-8α,9β-estra-1,3,5(10)-trien-17-one 
• 50394-95-1 3-hydroxyestra-1,3,5⁽¹⁰⁾-trienyl toluene-p-sulfonate 
• 7628-02-6 17β-hydrazoestra-1,3,5(10)-trien-3-ol 
• 141-52-6 sodium ethanolate 

Downstream Products

• 111200-38-5 5ξ,10ξ-estranol-(3ξ) 
• 29755-24-6 3-(trimethylsiloxy)estra-1,3,5(10)-triene 
• 14550-57-3 3-methoxy-1,3,5(10)-estratriene 
• 6561-98-4 10-Acetoxy-Δ^1,4-oestradienon-(3) (Oestra-p-chinolacetat) 
• 5506-56-9 2-Hydroxy-3-<4-nitro-2-benzoyl-phenoxy>-oestratrien-<1,3,5(10)> 
• 4999-72-8 2-Methoxy-3-<4-nitro-2-benzoyl-phenoxy>-oestratrien-<1,3,5(10)> 
• 1417896-42-4 C₂₆H₃₂O₂ 
• 1417896-43-5 C₂₈H₃₀F₆O₂ 
• 1417896-44-6 C₂₇H₃₄O₃ 
• 1417896-45-7 C₂₉H₃₈O₅ 
• 1417896-32-2 C₂₄H₂₈O 
• 1417896-33-3 C₂₆H₂₆F₆O 
• 1417896-34-4 C₂₅H₃₀O₂ 
• 1417896-35-5 C₂₇H₃₄O₄ 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 13α-estrone derivatives as potential antiproliferative agents

13α-Estrone derivatives containing various substituents on C-3 and C-17 were synthesized, and evaluated by means of MTT assays for in vitro antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, MCF-7, A2780 and A431). Compounds with N-benzyltriazolylmethoxy moieties on C-3 proved to be more potent than their 3-hydroxy or 3-ether counterparts. Some triazoles exerted substantial cytostatic effects against particular tumor cell lines, with submicromolar IC50 values.

Photochemical Behavior of Some Estrone Aryl and Methyl Sulfonates in Solution: Preparative and Mechanistic Studies

Direct irradiation of estrone aryl and methyl sulfonates in different organic solvents under nitrogen atmosphere was investigated under steady-state conditions. The estrone derivatives reacted efficiently through the photo-Fries rearrangement reaction involving [1;3]-sulfonyl migration providing the ortho-sulfonyl estrone derivatives and estrone as the photoproducts. In addition, estrone and 2-arylsulfonyl estrone derivatives were epimerized involving a Norrish Type-I reaction. Chemical quenching and photosensitization experiments on the photoreaction have been also carried out to establish the photoreactive excited state. Likewise, the solvent effect and the nature of the sulfonyl group on the photoreactions have been also studied.

Nickel-Catalyzed Intramolecular Decarbonylative Coupling of Aryl Selenol Esters

This report describes a method for Ni-catalyzed intramolecular decarbonylative coupling, which enables the conversion of areneselenol esters to diaryl selenides. The inexpensive and readily available catalyst can be employed under mild reaction conditions for the construction of structurally diverse diaryl selenides, including heterocyclic and natural product derivatives. (Figure presented.).

Selectivity and Mechanism of Iridium-Catalyzed Cyclohexyl Methyl Ether Cleavage

Cationic bis(phosphine)iridium complexes are found to catalyze the cleavage of cyclohexyl methyl ethers by triethylsilane. Selectivity for C-O cleavage is determined by the relative rates of SN2 demethylation versus SN1 demethoxylation, with the axial or equatorial disposition of the silyloxonium ion intermediate acting as an important contributing factor. Modulation of the electron-donor power of the supporting phosphine ligands enables a switch in selectivity from demethylation of equatorial methyl ethers to 2° demethoxylation. Applications of these accessible catalysts to the selective demethoxylation of the 3α-methoxy group of cholic acid derivatives is demonstrated, including a switch in observed selectivity controlled by 7α-substitution. The resting state of the catalyst has been characterized for two phosphine derivatives, demonstrating that the observed switch in C-O cleavage selectivity likely results from electronic factors rather than from a major perturbation of the catalyst structure.

Photo-Fries Rearrangement of Some 3-Acylestrones in Homogeneous Media: Preparative and Mechanistic Studies

Irradiation of a series of 3-acylestrones under a nitrogen atmosphere in cyclohexane, acetonitrile (MeCN), and methanol (MeOH) was investigated under steady-state conditions. The molecules underwent the photo-Fries rearrangement, with concomitant homolytic fragmentation of the ester group and [1;3]-acyl migration. This pathway afforded the ortho-acyl estrone derivatives, the main photoproducts, together with estrone. During the irradiation of 3-benzoyl estrone, epimerization of estrone through the Norrish type I reaction occurred, providing lumiestrone as the photoproduct. This photoreaction involves the fragmentation of the C-α at the carbonyl group (C-17) of the steroid. On the other hand, epimerization of ortho-regioisomer 2-acetyl estrone occurred during the irradiation of 3-acetyl estrone. Photosensitization with acetone and chemical quenching with N,N,N,N-tetramethyldiazetinedioxide of the photo-Fries reaction confirmed that the photoreaction took place from the singlet excited state while the Norrish type I reaction proceeds efficiently from the triplet excited state. Solvent effects, as well as the nature of the acyl group on the photoreactions, were also studied.

Reducing dehalogenating method of organic halogenated compound

The invention discloses a reducing dehalogenating method of an organic halogenated compound. The reducing dehalogenating method comprises: mixing an organic halogenated compound R-X, a non-noble metalpromoter, a sulfide and an alkali, and carrying out a reducing dehalogenating reaction to obtain a reducing product R-H, wherein R is at least one selected from alkyl and aryl, and X is at least oneselected from iodine, bromine and chlorine. According to the present invention, the types and the ratio (especially the specific type of the promoter) of various raw materials used in the reducing dehalogenating reaction, the corresponding reaction conditions and the like are researched and improved, such that the problems of use of highly-toxic or expensive reagent, poor tolerance of the group, narrow application range of the substrate and the like in the prior art can be effectively solved.

An efficient oxidative coupling method for synthesis of novel diastereomeric biaryl diols derived from estrone

An efficient oxidative coupling of estrogen derivatives was developed. Several 2-substitutent-17-deoxyestrones were applied to the aerobic oxidative coupling reactions catalyzed by CuCl2/TMEDA. The products were obtained as diastereoisomers wit

Synthesis and evaluation of analogues of estrone-3-O-sulfamate as potent steroid sulfatase inhibitors

Estrone sulfamate (EMATE) is a potent irreversible inhibitor of steroid sulfatase (STS). In order to further expand SAR, the compound was substituted at the 2- and/or 4-positions and its 17-carbonyl group was also removed. The following general order of p

Synthesis of 2- and 17-substituted estrone analogs and their antiproliferative structure-activity relationships compared to 2-methoxyestradiol

A novel series of 17-modified and 2,17-modified analogs of 2-methoxyestradiol (2ME2) were synthesized and characterized. These analogs were designed to retain or potentiate the biological activities of 2ME2 and have diminished metabolic liability. The ana

17-Aryl linker derivatised estrogen 3-sulphamates as inhibitors of steroid sulphatase

There is provided a compound comprising a steroidal ring system and a group R1 selected from any one of a sulphamate group, a phosphonate group, a thiophosphonate group, a sulphonate group or a sulphonamide group; wherein the D ring of the steroidal ring system is substituted by a group R2 of the formula —L—R3, wherein L is an optional linker group and R3 is an aromatic hydrocarbyl group.