34209-81-9

Basic information

• Product Name: 16,17-Epoxypregnenolone acetate
• Synonyms: 16a-17a-epoxypregnenoloneacetate;16-alpha,17-alpha-epoxy-20-oxopregn-5-en-3-beta-yl acetate;3b-Acetoxy-16a,17a-Epoxy-5-Pregnen-20-One;16,17-EPOXYPREGNENOLONE ACETATE 99+%;16α,17-Epoxy-3β-hydroxy-5-pregnen-20-one acetate, 3β-Acetoxy-16α,17α-epoxy-5-pregnen-20-one;16a,17a-Epoxy-20-oxopregn-5-en-3b-yl acetate;16α,17α-Epoxy-3β-(acetyloxy)pregn-5-en-20-one;20-Oxo-16α,17-epoxypregna-5-ene-3β-ol 3-acetate
• CAS NO: 34209-81-9
• Molecular Formula: C₂₃H₃₂O₄
• Molecular Weight: 372.5
• EINECS: 251-883-6
• Product Categories: Biochemistry;Steroids;Steroids (Others)
• Mol File: 34209-81-9.mol

Chemical Properties

• Melting Point: 159 °C
• Boiling Point: 469.5 °C at 760 mmHg
• Flash Point: 202.5 °C
• Appearance: /
• Density: 1.18 g/cm³
• Vapor Pressure: 5.5E-09mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: −20°C
• CAS DataBase Reference: 16,17-Epoxypregnenolone acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 16,17-Epoxypregnenolone acetate(34209-81-9)
• EPA Substance Registry System: 16,17-Epoxypregnenolone acetate(34209-81-9)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 34209-81-9(Hazardous Substances Data)

Usage

Uses

Used in Cancer Therapy:
16,17-Epoxypregnenolone acetate is used as an anticancer agent for its potential to inhibit the growth of cancer cells by inducing apoptosis, a process of programmed cell death. This property makes it a promising candidate for the development of new cancer treatments.
Used in Anti-Angiogenesis Applications:
In the field of anti-angiogenesis, 16,17-Epoxypregnenolone acetate is used to inhibit the formation of new blood vessels, which is crucial for tumor growth and metastasis. By preventing angiogenesis, this compound may help to limit the spread of cancerous cells and reduce the severity of the disease.
Used in Pharmaceutical Research:
16,17-Epoxypregnenolone acetate is used as a subject of pharmaceutical research to further understand its mechanisms of action and potential clinical applications. Ongoing studies aim to explore its full potential as an anticancer agent and to determine the most effective ways to utilize it in cancer treatment.
Used in Drug Development:
In the drug development industry, 16,17-Epoxypregnenolone acetate is used as a lead compound for the creation of new pharmaceuticals targeting cancer. Its unique properties and potential to induce apoptosis and inhibit angiogenesis make it a valuable asset in the search for novel cancer therapies.

InChI:InChI=1/C23H32O4/c1-13(24)23-20(27-23)12-19-17-6-5-15-11-16(26-14(2)25)7-9-21(15,3)18(17)8-10-22(19,23)4/h5,16-20H,6-12H2,1-4H3

Upstream product

• 13635-12-6 3β-acetoxy-16α,17α-epoxypregn-5-en-20-ol 
• 1162-53-4 16-dehydropregnenolone 
• 21853-84-9 3β,21-Diacetoxy-16α,17α-epoxypregn-5-en-20-one 
• 94977-68-1 16α,17α-epoxy-18-iodopregn-5-en-20-one 
• 563-63-3 silver(I) acetate 
• 108-24-7 acetic anhydride 
• 974-23-2 3β-hydroxy-16α,17α-epoxypregn-5-en-20-one 
• 979-02-2 16-dehydropregnenolone acetate 

Downstream Products

• 23357-24-6 3β,16β-diacetoxy-17α-hydroxypregn-5-en-20-one 
• 3885-13-0 Δ⁵-pregnene-3β,16α,20α-triol 
• 1569483-39-1 C₃₀H₃₆O₄ 
• 1569483-38-0 (E)-3β-acetoxy-16α,17α-epoxy-21-(4-nitrobenzal)pregn-5-en-20-one 
• 3517-33-7 3β,17,21-triacetoxy-pregn-5-en-20-one 
• 3517-42-8 17α-hydroxy-3β,21-diacetoxy-5-pregnen-20-one 
• 135300-60-6 17-hydroxy-3β-triphenylmethoxy-20-oxopregn-5-en-11α-yl hydrogen butanedioate 
• 135300-59-3 11α,17-dihydroxy-3β-triphenylmethoxypregn-5-en-20-one 
• 17291-60-0 17-hydroxy-20-oxopregn-5-en-3β-yl p-toluenusulfonate 
• 387-79-1 17-Hydroxypregnenolone 
• 74910-38-6 C₃₁H₃₆ClN₃O₆ 
• 74910-37-5 C₃₁H₃₅N₃O₆ 
• 82139-94-4 18,20-epoxy-20-ethoxypregn-5-ene-3β,16α-diol 3-acetate 16-benzoate 
• 82139-96-6 Benzoic acid (3S,8R,9S,10R,13R,14S,16R,17R)-3-acetoxy-17-acetyl-13-iodomethyl-10-methyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester 

Relevant articles and documents

Bismuth(III) triflate-catalyzed rearrangement of 16α,17α-epoxy-20-oxosteroids. Synthesis and structural elucidation of new 16α-substituted 17α-alkyl-17β-methyl-Δ13-18-norsteroids

The use of bismuth(III) triflate for the rearrangement of 16α,17α-epoxy-20-oxosteroids is reported. The reactions occur under truly catalytic conditions to afford novel 17α-alkyl-17β-methyl-Δ13-18-nor products bearing different O-containing substituents at C16. When the reaction is performed in the absence of acylation agent a mixture of isomeric 16α- and 16β-hydroxy derivatives is obtained, whereas when carried out in the presence of such reagents, the reaction selectively affords the corresponding 16α-acyl rearranged products. The chemoselective rearrangement of 5β,6β;16α,17α-diepoxy-20-oxopregnan-3β-yl acetate to afford a 'backbone' rearranged product bearing the 16α,17α-epoxide group is also reported. Some mechanistic considerations are provided. All rearranged products were the subject of comprehensive structural elucidation, by the use of X-ray crystallography and 2D NMR.

Evaluation of new pregnane derivatives as 5α-reductase inhibitor

The objective of this study was to synthesize several new pregnane derivatives and evaluate them as antiandrogens. From the commercially available 16-dehydropregnenolone acetate (7), two new steroidal compounds were synthesized: 17α-hydroxy-17β-methyl-16β-phenyl-D-homoandrosta-1,4.6- triene-3,20-dione (18) and 17α-acetoxy-17β-methyl-16β-phenyl-D-homoandrosta-1,4.6- triene-3,20-dione (19). The 5α-reductase inhibitory effect of the new compounds 18 and 19 together with the previously synthesized intermediates 7, 8, 13, 16, and 17 was determined in three different models: gonadectomized hamster flank organs diameter size, incorporation of [1,2-14C]sodium acetate into lipids in flank organs and conversion of [3H]testosterone (T) to [3H]dihydrotestosterone (DHT) by Penicillium crustosum. The evaluation of these steroids was carried out with three different controls: one group was treated with vehicle, the second with T and the third group with T plus finasteride. The pharmacological results from this work demonstrated that T significantly increases the diameter of the pigmented spot on the flank organs (p3H]T to [3H]DHT in a manner comparable to that of the flank organs. All experiments indicated that finasteride as well as steroids 7, 8, 13, 16-19 reduced significantly the conversion of T to DHT in P. crustosum. These compounds also decrease the size of the pigmented spot in the flank organs as well as reducing the incorporation of radiolabeled sodium acetate into lipids; T and the control sample (treated with vehicle only) were used for comparison. Apparently the presence of the 4,6-diene-3,20-dione moiety and also the C-17 ester group produce a higher inhibitory effect on the parameters used. PPThe data from this study indicated also that the three models used for the pharmacological evaluation exhibited comparable results.

Androgenic and anti-androgenic effects of progesterone derivatives with different halogens as substituents at the C-6 position

The pharmacological activities of four pregnane derivatives:17α- hydroxy-16β-methylpregna-4,6-diene-3,20-dione (7), 17α-acetoxy-16β- methylpregna-4,6-diene-3,20-dione (8), 17α-acetoxy-6-bromo-16β- methylpregna-4,6-diene-3,20-dione (10), and 17α-acetoxy-6-chloro-16β- methylpregna-4,6-diene-3,20-dione (11), were determined. The derivatives were evaluated on gonadectomized male hamster flank organs and seminal vesicles. The results indicate that topical applications of testosterone (T) on the flank organs increased the diameter of the pigmented spot. Similarly, the same phenomenon occurred on the glands treated with compound 11, whereas compound 10 decreased the size of the spot significantly. In this study, we determined the effects of several new steroids on the conversion of T to DHT in flank organs and seminal vesicles. The results show that compound 10 inhibited T conversion to DHT, but compound 11, at a dose of 200 μg, stimulated T conversion in both flank organs and seminal vesicles. However, when 2 mg of compound 11 was applied, it inhibited the conversion of T to DHT, suggesting that this compound also represses gonadotropin release. The difference between compounds 10 and 11 involves the electronegativity of the halogen at the C-6 position of the progesterone skeleton. These data clearly indicate that by decreasing the electronegativity of the halogen at C-6 (compound 10), 5α-reductase is inhibited in both tissues and at different pHs. On the other hand, when the electronegativity of the halogen atom was increased (11), there was a much lower inhibitory effect on the conversion of T to DHT.

17α-acetoxy-17β-methyl-16β-phenyl-D-homo-4,6-pregnadiene-3, 17a-dione: Synthesis and crystal structure determination of a new rearranged pregnane derivative

The title compound is C29H34O4, tetragonal, P43, a = b = 10.310(1), c = 23.871(2)A. The A, B, C, and D rings adopt envelope, half-chair, chair, and distorted chair conformations, respectively. The phenyl ring is planar. The methyl substituents at the A/B, C/D, and at C(17) are axial; and the -OCOCH3 group at C(17) and phenyl ring at C(16) are equatorial. The molecules in the crystal are held together by van der Waals forces and several C - H···O hydrogen bond interactions.

The first synthesis of the aglycone of the potent anti-tumor steroidal saponin OSW-1

The protected aglycone (21e-β) of the potent anti-tumor agent OSW-1 (1) was synthesized in 9 steps from 5-androsten-3β-ol-17-one (10) in 55% overall yield. Key reactions involve ene installation of the side chain, regio and stereoselective dihydroxylation and diastereoselective reduction of the C16 ketone.

Sonochemical Reduction of α,β-Epoxy Ketones and α'-Oxygenated Analogs by Aluminium Amalgam

The sonochemical reductive opening of α,β-epoxy ketones and their α'-oxygenated (-OH or -OAc) analogs by aluminium amalgam allows shorter reaction times, better yields of the respective β-hydroxy ketones and minimization of by-products.The rates of these reactions are affected by the intensity of the acoustic waves and by temperature.

3β-11α-17-TRIHYDROXY-5-PREGNEN-20-ONE 11-HEMISUCCINATE AS A HAPTENE FOR RIA OF ''17α-HYDROXYPREGNENOLONE''

6β,17-Dihydroxy-3α,5-cyclo-5α-pregnan-20-one (VII) and 17-hydroxy-6β-methoxy-3α,5-cyclo-5α-pregnan-20-one (IX) were hydroxylated into the position 11α using Rhizopus nigricans fungi culture, and then selectively converted into haptene XIII for the RIA determination of 3β,17-dihydroxypregn-5-en-20-one (IV).

18-Substituted Steroids. Part 11. Synthesis of 3&β,16&α,18-Trihydroxyandrost-5-en-17-one, a Neonatal Urinary Metabolite, and the 3,16,18-Triaceate of Its 16&β-Epimer

3β,16α,18-Trihydroxyandrost-5-en-17-one and the triacetate of its 16β-epimer have been synthesized from 3β-hydroxypregna-5,16-dien-20-one via the 'hypoiodite' reaction of the derived 3β-acetoxy-16α,17α-epoxypregn-5-en-20-ols to functionalize C-18, followed by controlled opening of the epoxide ring by reagents chosen to give either 3β,16α,18- or 3β,16β,18-triacetoxy-17α-hydroxypregn-5-en-20-one.Reduction of the 20-oxo group and oxidative cleavage of the C(17) - C(20) bond produced the corresponding 3β,16,18-triacetoxyandrost-5-en-17-one. 3β,16α,18-Trihydroxyandrost-5-en-17-one was obtained by deacetylation of its triacetate, but the 16β-epimer rearranged on hydrolysis to give 3β,17β,18-trihydroxyandrost-5-en-16-one.The androst-5-ene-3β,16,17β,18-tetraols were also prepared.