10162-99-9

Basic information

• Product Name: (2beta,3beta,5beta,14xi)-2,3,14-trihydroxypregn-7-ene-6,20-dione
• Synonyms: poststerone;Pregn-7-ene-6,20-dione, 2,3,14-trihydroxy-, (2β,3β,5β)-
• CAS NO: 10162-99-9
• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.4599
• Mol File: 10162-99-9.mol

Chemical Properties

• Boiling Point: 546.3°C at 760 mmHg
• Flash Point: 298.2°C
• Density: 1.28g/cm³
• Vapor Pressure: 3.27E-14mmHg at 25°C
• Refractive Index: 1.592
• CAS DataBase Reference: (2beta,3beta,5beta,14xi)-2,3,14-trihydroxypregn-7-ene-6,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (2beta,3beta,5beta,14xi)-2,3,14-trihydroxypregn-7-ene-6,20-dione(10162-99-9)
• EPA Substance Registry System: (2beta,3beta,5beta,14xi)-2,3,14-trihydroxypregn-7-ene-6,20-dione(10162-99-9)

Safety Data

• Hazardous Substances Data: 10162-99-9(Hazardous Substances Data)

Usage

Uses

Used in Gynecological and Reproductive Medicine:
(2beta,3beta,5beta,14xi)-2,3,14-trihydroxypregn-7-ene-6,20-dione is used as a medication for the treatment of various gynecological and reproductive disorders, such as menstrual irregularities, infertility, and hormone replacement therapy. It helps regulate hormonal balance and supports the normal functioning of the reproductive system.
Used in Research:
(2beta,3beta,5beta,14xi)-2,3,14-trihydroxypregn-7-ene-6,20-dione is used as a precursor in the synthesis of other steroid hormones. It serves as an important compound in the development of new medications and therapies for various conditions related to hormonal imbalances and reproductive health.
Used in Pharmaceutical Industry:
(2beta,3beta,5beta,14xi)-2,3,14-trihydroxypregn-7-ene-6,20-dione is used as an active pharmaceutical ingredient in the formulation of drugs for the treatment of gynecological and reproductive disorders. It is incorporated into medications to provide therapeutic benefits to patients suffering from hormonal imbalances and related conditions.

Upstream product

• 5289-74-7 20-Hydroxyecdysone 
• 19399-09-8 (3aS,5aR,6aR,9aS,10aR,12aR)-1-Acetyl-3a-hydroxy-8,8,10a,12a-tetramethyl-1,2,3,3a,5a,6,6a,9a,10,10a,10b,11,12,12a-tetradecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one 
• 104211-77-0 C₃₂H₄₈O₈ 
• 17086-76-9 cyasterone 
• 84507-67-5 (3aS,5aR,6aR,9aS,10aR,12aR)-3a-Hydroxy-8,8,10a,12a-tetramethyl-1-((1R,2R)-1,2,5-trihydroxy-1,5-dimethyl-hexyl)-1,2,3,3a,5a,6,6a,9a,10,10a,10b,11,12,12a-tetradecahydro-7,9-dioxa-dicyclopenta[a,h]phenanthren-5-one 
• 5289-74-7 β-ecdysterone 
• 67-56-1 methanol 
• 76808-40-7 2β,3β,14-tris-(trimethylsilanyloxy)-5β-pregn-7-ene-6,20-dione 
• 123171-35-7 tert-Butyl-[4-((S)-2-methyl-2,3-dihydro-furan-2-yl)-butoxy]-diphenyl-silane 

Downstream Products

• 123171-52-8 (20R,25S)-27(3-(tert-butyl-diphenyl-silanyloxy)-propyl)-2β,3β,14,20,25,5β-pentahydroxycholest-7-ene-6,22-dione 
• 123171-52-8 (20R,25R)-27(3-(tert-butyl-diphenyl-silanyloxy)-propyl)-2β,3β,14,20,25,5β-pentahydroxycholest-7-ene-6,22-dione 
• 5289-74-7 20-Hydroxyecdysone 

Relevant articles and documents

Backstabbing P-gp: Side-chain cleaved ecdysteroid 2,3-dioxolanes hyper-sensitize MDR cancer cells to doxorubicin without efflux inhibition

P-glycoprotein (P-gp, ABCB1) over-expression, causing a multi-drug resistant (MDR) phenotype, is a major problem in cancer chemotherapy that urgently requires novel approaches. Our previous studies showed certain ecdysteroid derivatives as promising chemo-sensitizers against MDR and non-MDR cancer cell lines while also exerting mild to moderate inhibition of P-gp function. Here we report the preparation of a set of substituted 2,3-dioxolane derivatives of poststerone, a known in vivo metabolite of 20-hydroxyecdysone (20E). In contrast with previously studied ecdysteroid dioxolanes, the majority of the new compounds did not inhibit the efflux function of P-gp. Nevertheless, a strong, dose dependent sensitization to doxorubicin was observed on a P-gp transfected cancer cell line and on its susceptible counterpart. We also observed that the MDR cell line was more sensitive to the compounds' effect than the non-MDR. Our results showed for the first time that the chemo-sensitizing activity of ecdysteroids can be fully independent of functional efflux pump inhibition, and suggest these compounds as favorable leads against MDR cancer.

Side-chain cleaved phytoecdysteroid metabolites as activators of protein kinase B

Phytoecdysteroids exert their non-hormonal anabolic and adaptogenic effects in mammals, including humans, through a partially revealed mechanism of action involving the activation of protein kinase B (Akt). We have recently found that poststerone, a side-chain cleaved in vivo metabolite of 20-hydroxyecdysone, exerts potent anabolic activity in rats. Here we report the semi-synthetic preparation of a series of side-chain cleaved ecdysteroids and their activity on the Akt phosphorylation in murine skeletal muscle cells. Twelve C-21 ecdysteroids including 8 new compounds were obtained through the oxidative side-chain cleavage of various phytoecdysteroids, or through the base-catalyzed autoxidation of poststerone. The complete 1H and 13C NMR spectroscopic assignments of the new compounds are presented. Among the tested compounds, 9 could activate Akt stronger than poststerone revealing that side-chain cleaved derivatives of phytoecdysteroids other than 20-hydroxyecdysone are valuable bioactive metabolites. Thus, our results suggest that the expectable in vivo formation of such compounds should contribute to the bioactivity of herbal preparations containing ecdysteroid mixtures.

Rapid, laser-induced conversion of 20-hydroxyecdysone-A follow-up study on the products obtained

We have recently reported the set-up of an experimental system for the laser-induced photochemical modification of bioactive substances, where two ecdysteroids, 20-hydroxyecdysone (20E) and its diacetonide derivative served as probes. As a direct continuation of our previous work, three new compounds together with five other ecdysteroid derivatives, have been identified from the novel, laser-induced photo-transformation reaction of 20E. The structures and NMR signal assignment were established by comprehensive one- and two-dimensional NMR spectroscopy supported by mass spectroscopy. Possible ways for the formation of each species is also discussed. Similar to their parental compound, the products obtained are potentially bioactive and worthy for further investigations; due to the low yields, however, a different approach for their higher scale production is suggested.

First example of trifluoromethylation in the ecdysteroid series. Synthesis of (20RS)-20-O-hydro-20-trifluoromethylpoststerone

The title compound was synthesized by trifluoromethylation of poststerone derivatives with trimethyl(trifluoromethyl)silane in the presence of tetrabutylammonium fluoride.

Jones Oxidation of 20-Hydroxyecdysone (Crustecdysone)

Oxidation of 20-hydroxyecdysone (crustecdysone) (4) with Jones reagent gives a 2:1 mixture of posterone (1) and its 3-keto derivative (2).A possible source of (2) is suggested.

A facile route to 20-hydroxyecdysone and side chain homologues from poststeron

A flexible approach to ecdysteroids, chain elongated at C-26 and C-27, is reported. Key features are the addition of 5-lithio 2,3-dihydrofurans (3) to poststeron (10) and a stereoselective reduction of the 22-∞ group.

SYNTHESIS OF C27-SUBSTITUTED ECDYSTEROIDS, POTENTIAL TOOLS FOR BIOCHEMICAL STUDIES

A sequence of selective protection procedures is described, facilitating the efficient cleavage of the ecdysteroid side-chain, which can then be reconstructed; in this way, C-27 ether-linked analogues of ecdysteroids have been synthesized, one of which di