23670-94-2

Basic information

• Product Name: stigmast-4-ene-3,6-dione
• Synonyms: stigmast-4-ene-3,6-dione;(24R)-24-Ethylcholest-4-ene-3,6-dione
• CAS NO: 23670-94-2
• Molecular Formula: C₂₉H₄₆O₂
• Molecular Weight: 426.67
• Product Categories: Steroids
• Mol File: 23670-94-2.mol

Chemical Properties

• Melting Point: 172-174℃
• Boiling Point: 523.4°Cat760mmHg
• Flash Point: 192.8°C
• Appearance: /
• Density: 1.01g/cm³
• Vapor Pressure: 4.73E-11mmHg at 25°C
• Refractive Index: 1.521
• CAS DataBase Reference: stigmast-4-ene-3,6-dione(CAS DataBase Reference)
• NIST Chemistry Reference: stigmast-4-ene-3,6-dione(23670-94-2)
• EPA Substance Registry System: stigmast-4-ene-3,6-dione(23670-94-2)

Safety Data

• Hazardous Substances Data: 23670-94-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Stigmast-4-ene-3,6-dione is used as a pharmaceutical agent for its anti-inflammatory properties, helping to reduce inflammation in the body and potentially managing inflammatory conditions.
Used in Antioxidant Applications:
As an antioxidant, Stigmast-4-ene-3,6-dione is used to combat oxidative stress and protect cells from damage caused by free radicals, contributing to overall health and wellness.
Used in Cancer Treatment:
Stigmast-4-ene-3,6-dione is used as an anti-cancer agent, potentially inhibiting the growth and proliferation of cancer cells, and providing a novel approach to cancer therapy.
Used in Diabetes Management:
Stigmast-4-ene-3,6-dione is used as a potential treatment for diabetes, where it may help regulate blood sugar levels and improve insulin sensitivity.
Used in Obesity Treatment:
In the context of obesity, Stigmast-4-ene-3,6-dione is used as a potential therapeutic agent to address weight management and related metabolic issues.
Overall, Stigmast-4-ene-3,6-dione's diverse applications in the pharmaceutical, health, and wellness industries highlight its potential as a multifaceted compound with significant implications for medical and health-related research and development.

InChI:InChI=1/C29H46O2/c1-7-20(18(2)3)9-8-19(4)23-10-11-24-22-17-27(31)26-16-21(30)12-14-29(26,6)25(22)13-15-28(23,24)5/h16,18-20,22-25H,7-15,17H2,1-6H3/t19-,20-,22+,23-,24+,25+,28-,29-/m1/s1

Upstream product

• 6035-62-7 (10R)-3c-Acetoxy-10r.13c-dimethyl-17c-((R)-1-methyl-4-isopropyl-hexen-(4t)-yl)-(8cH.9tH.14tH)-Δ⁵-tetradecahydro-1H-cyclopenta[a]phenanthren 
• 16137-56-7 3,5,6-trihydroxysitostane 
• 83-46-5 β-sitosterol 
• 7647-01-0 hydrogenchloride 
• 67-66-3 chloroform 
• 74395-55-4 (24R)-24-ethyl-5α-cholestan-5-ol-3,6-dione 
• 64-19-7 acetic acid 
• 67-56-1 methanol 

Relevant articles and documents

Synthesis and cytotoxic analysis of some disodium 3β,6β-dihydroxysterol disulfates

Disodium 3β,6β-dihydroxy-5α-cholestane disulfate (1) was synthesized in 4 steps with a high overall yield from cholesterol. First, cholesterol (4a) was converted to cholest-4-en-3,6-dione (5a) via oxidation with pyridinium chlorochromate (PCC) and then 5a was reduced by NaBH4 in the presence of NiCl2 to produce cholest-3β,6β-diol (6a). The reaction of 6a with the triethylamine-sulfur trioxide complex generated diammonium 3β,6β-dihydroxy-5α-cholestane disulfate (7a) and the treatment of 7a by cation exchange resin 732 (sodium form)(Na+) yielded the target steroid 1. Disodium 24-ethyl-3β,6β-dihydroxycholest-22-ene disulfate (2) and disodium 24-ethyl-3β,6β-dihydroxycholestane disulfate (3) were synthesized using a similar method. The cytotoxicity of these compounds against Sk-Hep-1 (human liver carcinoma cell line), H-292 (human lung carcinoma cell line), PC-3 (human prostate carcinoma cell line) and Hey-1B (human ovarian carcinoma cell line) cells was investigated. Our results indicate that presence of a cholesterol-type side chain at position 17 is necessary for their biological activity.

A facile and efficient synthesis of some (6E)-hydroximino-4-en-3-one steroids, steroidal oximes from Cinachyrella spp. sponges

Using β-sitosterol as a starting material, (6E)-hydroximino-24-ethylcholest-4-en-3-one (1), a natural steroidal oxime from Cinachyrella alloclada and C. apion, was synthesized in four steps with a high overall yield. First, β-sitosterol (5a) is transformed into the corresponding 24-ethylcholest-4-en-3,6-dione (6a) via oxidation with pyridinium chlorochromate (PCC). Selective reduction of 6a by NaBH4 in the presence of CoCl2 gives 24-ethylcholest- 4-en-3β-ol-6-one (7a). The reaction of 7a with hydroxylamine hydrochloride offers the oxime 8a and the oxidation of 8a by Jones reagent gives the target steroid 1. (6E)-Hydroximinocholest-4-en-3-one (2) and (6E)-hydroximino-24-ethylcholest-4,22-dien-3-one (4) were synthesized by a similar method. The cytotoxicity of the synthesized compounds against sk-Hep-1 (human liver carcinoma cell line), H-292 (human lung carcinoma cell line), PC-3 (human prostate carcinoma cell line) and Hey-1B (human ovarian carcinoma cell line) cells were investigated. The presence of a cholesterol-type side chain appears to be necessary for the biological activity.

Design, synthesis and evaluation of wound healing activity for β-sitosterols derivatives as potent Na+/K+-ATPase inhibitors

β-Sitosterols, is a common steroid that can be identified in a variety of plants and their efficacy in promoting wound healing has been demonstrated. Na+/K+-ATPase, more than a pump, its signal transduction function for involvement in cell growth regulation attracts widespread concern. The Na+/K+-ATPase/Src receptor complex can serve as a receptor involved in multiple signaling pathways including promoting wound healing pathways. To finding potent accelerating wound healing small molecular, we choose the high inhibitory activity of Na+/K+-ATPase and non-cardiotoxic natural compound, β-sitosterol as the substrate. A series of β-sitosterol derivatives were designed, synthesized and evaluated as potential Na+/K+-ATPase inhibitors. Among them, compounds 31, 47, 49, showed improved inhibitory activity on Na+/K+-ATPase, with IC50 value of 3.0 μM, 3.4 μM, 2.2 μM, which are more potent than β-sitosterol with IC50 7.6 μM. Especially, compound 49 can induce cell proliferation, migration and soluble collagen production in L929 fibroblasts. Compared to model, compound 49 can accelerate wound healing in SD rats. Further studies indicated that 49 can activate the sarcoma (Src), uptake the protein kinase B (Akt), extracellular signal-regulated kinase (ERK) proteins expression in a concentration dependent manner. Finally, binding mode of compound 49 with Na+/K+-ATPase was studied, which provides insights into the determinants of potency and selectivity. These results proved β-stitosterol derivative 49 can serve as an effective inhibitor of Na+/K+-ATPase and potential candidate for accelerating wound healing agents.

Sterol derivatives and its preparation method and application

The invention discloses a sterol derivative of beta-sitosterol, beta-stigmasterol and cholesterol, and is shown as a formula VI. The invention also discloses a preparation method of the sterol derivative. The invention also discloses application of the sterol derivative to the aspect of preparation of wound healing promoting medicine. By starting from easily obtained natural products, the beta-sitosterol, the beta-stigmasterol and the cholesterol are used as starting raw materials; the synthetic method is simple; better operability and reaction yield are realized. The prepared sterol derivative has the obvious wound healing promoting activity; the multiplication, migration and collagen synthesis capability on L929 mechanocytes is obviously higher than that of the raw material and positive control medicine recombinant human bFGF (basic fibroblast growth factor). Compared with protide type medicine (such as bFGF), the prepared sterol derivative has more diversified dosage forms and medication modes; the reference is provided for the application in the field of wound healing promoting. The formula VI is shown as the accompanying diagram.

Synthesis and evaluation of some steroidal oximes as cytotoxic agents: Structure/activity studies (I)

The side chain of a compound plays an important role in its biological function. In our studies, we have found that hydroximinosteroid derivatives with different side chains and position of hydroximino on ring A and B displayed remarkable distinct cytotoxicities against a diversity of cancer cell types. Presence of an oxime group on ring B and a hydroxy on ring A or B resulted in a higher cytotoxicity than other structural motifs. In addition, a cholesterol-type side chain at position 17 was required for the biological activity. Our findings provide new evidence showing the relationship between the chemical structure and biological function. The information obtained from the studies may be useful for the design of novel chemotherapeutic drugs.

Chemical Constituents of Piper betle Linn. (Piperaceae) roots

Column chromatography of the alcoholic extract of Piper betle roots furnished aristololactam A-II and a new phenyl propene, characterized as 4-allyl resorcinol, while the petroleum-ether extract yielded a diketosteroid, viz. stigmast-4-en-3,6-dione. All these compounds were characterized by spectroscopic means. Isolation of these compounds from this source is being reported here for the first time.

Stereospecific oxidation of 3β-hydroxysteroids by persolvent fermentation with Pseudomonas sp. ST-200

Pseudomonas sp. strain ST-200 isolated from a humus soil effectively oxidizes cholesterol dissolved in organic solvents but not that suspended in the growth medium. The organism does not assimilate cholesterol. This organism oxidized a variety of 5α- or 5-ene-steroids dissolved in organic solvent. First, the 3β-OH group was oxidized to a ketone group. The 3α-OH group was scarcely oxidized. Successively, C-6 position of 5-ene-steroids was hydroxylated, and a double bond of 5-ene-steroids was transferred from Δ5 to Δ4. Then, the 6-OH group was oxidized to a ketone group. Persolvent fermentation with ST-200 would provide an effective, convenient, and stereospecific method to oxidize the C-3 and C-6 positions of steroids.

Oxidation of steroidal 5-en-3β-ols with Jones reagent in ether

The two-phase oxidation of steroidal 5-en-3β-ol (via 5-en-3-ones) into corresponding 4-en-3,6-diones in diethyl ether with Jones reagent was investigated. It was found that the system Jones reagent/diethyl ether enables short reaction times and easy isolation of the obtained products. The exclusive abstraction of 4α-hydrogen during oxidation, together with molecular mechanics (MM2), and semiempirical (PM3) calculations, suggest that boat conformation of ring A precedes the formation of corresponding radicals (or cations).

Oxidation of homoallylic steroidal alcohols with pyridinium chlorochromate. The synthesis of steroidal 4-en-3,6-diones

Prolonged oxidation of steroidal homoallylic Δ5-3-alcohols with pyridinium chlorochromate (PCC) in dichloromethane affords the corresponding Δ4-3,6-diones via the intermediate Δ5-3-one and not a Δ4-3-one.