3434-45-5

Basic information

• Product Name: 3,17β-Bis(acetyloxy)-1,3,5(10)-estratrien-6-one
• Synonyms: 3,17β-Bis(acetyloxy)-1,3,5(10)-estratrien-6-one
• CAS NO: 3434-45-5
• Molecular Formula: C₂₂H₂₆O₅
• Molecular Weight: 370.43884
• Mol File: 3434-45-5.mol

Chemical Properties

• Boiling Point: 489.7°Cat760mmHg
• Flash Point: 212.9°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 9.74E-10mmHg at 25°C
• Refractive Index: 1.569
• CAS DataBase Reference: 3,17β-Bis(acetyloxy)-1,3,5(10)-estratrien-6-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,17β-Bis(acetyloxy)-1,3,5(10)-estratrien-6-one(3434-45-5)
• EPA Substance Registry System: 3,17β-Bis(acetyloxy)-1,3,5(10)-estratrien-6-one(3434-45-5)

Safety Data

• Hazardous Substances Data: 3434-45-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
3,17β-Bis(acetyloxy)-1,3,5(10)-estratrien-6-one is used as a research compound for studying the structure-activity relationships of estrogen hormones and their analogs. Its structural similarity to natural estrogens allows researchers to investigate its biological activities and potential pharmaceutical uses in hormone-related research.
Used in Hormone-Related Research:
3,17β-Bis(acetyloxy)-1,3,5(10)-estratrien-6-one is used as a hormone analog in research aimed at understanding the mechanisms of action and potential therapeutic applications of estrogen hormones. Its unique structural features may provide insights into the development of new drugs targeting estrogen receptors or related pathways.

InChI:InChI=1/C22H26O5/c1-12(23)26-14-4-5-15-16-8-9-22(3)19(6-7-21(22)27-13(2)24)17(16)11-20(25)18(15)10-14/h4-5,10,16-17,19,21H,6-9,11H2,1-3H3/t16-,17-,19+,21+,22+/m1/s1

Upstream product

• 1474-52-8 estradiol-3,17-diacetate 
• 50-28-2 estradiol 
• 40550-71-8 17β-acetoxy-4-estrene-3,6-dione 
• 4999-76-2 3,17β-diacetoxyoestra-3,5-diene 
• 434-22-0 19-nortestosterone 
• 6599-92-4 17β-acetoxy-3-hydroxy-1,3,5(10)-estratriene-6-one 
• 108-24-7 acetic anhydride 

Downstream Products

• 1229-24-9 6α-hydroxyestradiol 
• 6626-42-2 3,6,17-Triacetat v. 6α-Hydroxyoestradiol 
• 6944-48-5 estratriene-(1,3,5(10))-triyl-(3,6β,17β)-triacetate 
• 6599-92-4 17β-acetoxy-3-hydroxy-1,3,5(10)-estratriene-6-one 
• 571-92-6 6-ketoestradiol 
• 35048-47-6 6-keto-1,3,5(10)estratriene-3,17β-diol 6-carboxymethyloxime 
• 1971-65-9 Estra-1,3,5(10),6-tetraene-3,17β-diol Diacetate 
• 123044-29-1 3,17β-dihydroxyoestra-1,3,5(10)-trien-6-one tosylhydrazone 
• 38002-18-5 17α-ethynyl-3,17β-dihydroxyestra-1,3,5(10)-trien-6-one 
• 1476-34-2 6-oxoestrone 
• 7291-41-0 6-Dehydroestradiol 
• 86270-61-3 6α-bis(2-hydroxyethyl)amino-3-benzyloxy-1,3,5(10)-estratriene-17β-ol 
• 86270-58-8 6α-acetamido-3-benzyloxy-1,3,5(10)-estratriene-17β-ylacetate 
• 86270-60-2 6α-amino-3-benzyloxy-1,3,5(10)-estratriene-17β-ol 

Relevant articles and documents

CHROMIC ANHYDRIDE-3,5-DIMETHYLPYRAZOLE COMPLEX: AN EFFICIENT REAGENT FOR OXIDATION OF STEROIDAL ESTROGENS TO 6-OXO-DERIVATIVES

An efficient procedure for the oxidation of steroidal estrogens to the corresponding 6-oxo-derivatives is described.The oxidative process involves the use of 3,5-dimethylpyrazole-chromium trioxide complex at low temperature (-20 deg).Under these conditions, only the 6-oxo-derivative and the unreacted starting material were obtained and the latter could be subjected to oxidation once again to obtain additional amount of 6-oxo-derivative.

An efficient synthesis of 6-oxo-17-β-estradiol and its O-carboxymethyl oxime

Estradiol was efficiently oxidized into 6-oxo estradiol using pyridinium chlorochromate. Previously reported yields were considerably increased by the use of oxidizing agent adsorbed onto celite. The oxo compound was then transformed into the corresponding O-carboxymethy] oxime derivative in quantitative yield.

Improved syntheses of 3,17β-diacetoxyestra-1,3,5(10)-trien-6-one

Improved syntheses of 3,17β-Diacetoxyestra-1,3,5(10)-trien-6-one 5 was achieved in 4 steps (respectively in 45% and 56% overall yield) from 19-nortestosterone 1.

Design, synthesis, and estrogenic activity of a novel estrogen receptor modulator - A hybrid structure of 17β-estradiol and vitamin E in hippocampal neurons

We recently discovered that ICI 182,780 (1), an antagonist of estrogen receptor (ER)-dependent proliferation in reproductive tissues, functions as an estrogenic agonist in primary neurons. The present study investigated whether the agonist properties of 1 in neurons could be translated into structural analogs. 7α-[(4R,8R)-4,8,-12-trimethyltridecyl]estra-1,3,5-trien-3, 17β-diol (2), a hybrid structure of 17β-estradiol and vitamin E, was synthesized and found to bind to both ERα and ERβ. In vitro analyses demonstrated that 2 was neuroprotective and effective in activating molecular mechanisms associated with estrogenic agonist activity in rat primary hippocampal neurons. Collectively, the data support an estrogenic agonist profile of 2 action comparable to 1 in primary neurons, confirming that estrogenic activity of 1 in neurons is not a unique phenomenon. These results provide support for the development of a brain-selective ER modulator, with potential as an efficacious and safe estrogen alternative to prevent Alzheimer's disease and cognitive decline in postmenopausal women.

6-(4'-chloro-1'-benzamide)-estrogen compound as well as preparation method and application thereof

The invention discloses a 6-(4'-chloro-1'-benzamide)-estrogen compound, which has the chemical structural formula shown in the specification, wherein R is any one of -C=O- or -H. The 6-(4'-chloro-1'-benzamide)-estrogen compound disclosed by the invention has an inhibiting effect on ovarian cancer cells, breast cancer cells and human cervical cancer cells.

An estradiol-conjugate for radiolabelling with 177Lu: An attempt to prepare a radiotherapeutic agent

177Lu is presently being considered as one of the most promising radionuclide for targeted therapy owing to its suitable decay characteristics. 177Lu in high radionuclidic purity (99.99%) and moderate specific activity (100-110 TBq/g) was produced using enriched (60.6% 176Lu) Lu2O3 target. The macrocycle 1,4,7,10- tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA) is known to form stable complexes with lanthanides. Herein, we describe a novel attempt to introduce 177Lu in the estradiol moiety through a steroidal-BFCA (Bifunctional Chelating Agent) conjugate. The preparation of a steroid conjugate via coupling of 6α-amino-17β-estradiol with a C-functionalized DOTA derivative viz. p-NCS-benzyl-DOTA as a BFCA and thereafter the radiolabelling of the conjugate with 177Lu is reported. Biological activity of the resultant estradiol-DOTA conjugate after radiolabelling was studied by carrying out preliminary in vitro cell uptake studies with MCF-7, human breast carcinoma cell line expressing estrogen receptors as well as binding studies with anti-estradiol antibodies.

Cytoprotective steroids (II)

A method is provided for treating a patient in need of therapy for acute neuronal degeneration due to metabolic compromise of central or peripheral nervous system cells comprising administering to that patient a therapeutically effective amount of a 7α-hydroxy substituted steroid selected from 7α-hydroxy-derivatives of estradiols, dehydroepiandrosterones and pregnenolones, and metabolic precursors thereof. Use of such compounds for manufacture of medicaments and neuroprotective compositions are also provided.

A Novel Efficient Approach to the Synthesis of 6-Oxo Ethinylestradiol and its 3-Isopropanesulfonate

Ethinylestradiol (1) was converted into the corresponding 6-oxo derivative 7 by a short and simple procedure involving acetate 10 and ketone 11.Phase transfer catalyzed esterification of compound 7 with propane-2-sulfonyl chloride gave sulfonate 12.

Bile acids. LXVIII. Allylic and benzylic photo-chemical oxidation of steroids

To provide 7-oxocholesterol derivatives in yields superior to those obtained by chemical oxidation, the preparation of steroidal allylic or benzylic ketones was studied. Air-induced oxidation was investigated with a highly selective low energy UV lamp in the presence of mercuric bromide. With this procedure cholesteryl acetate, 5-cholestene-3β,27-diol diacetate, 24(R)-24-methyl-5-cholesten-3β-yl acetate, 24(R)-24-methyl-5-cholesten-3β-yl acetate, 24(R)-24-ethyl-5-cholesten-3β-yl acetate and 24(R)-24-ethyl-(22E)-cholestra-5,22-dien-3β-yl acetae were oxidized to the allylic keto-derivative in good yeilds; estradiol-17β diacetate was similarly converted to the 6-oxo-product in improved yield. This method can be very useful in the synthesis of 7-oxocholesteryl acetate and its analogs and 6-oxo-estratrienes.