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95975-55-6

95975-55-6

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95975-55-6 Usage

Uses

Guggulsterone is a broad spectrum steroid receptor ligand. Gum resin of Commiphora mukul marketed as an antihyperlipidemic drug.

Biological Activity

Broad spectrum steroid receptor ligand; binds with high affinity to mineralocorticoid receptors (K i = 39 nM) and lower affinity to progesterone, androgen and glucocorticoid receptors (K i values are 201, 240 and 224 nM respectively). Functions primarily as an antagonist of these receptors, with the exception of the progesterone receptor where it displays partial agonist effects. Also exerts hypolipidemic activity, likely via antagonism of the receptor for bile acids (farnesoid X receptor; FXR).

Check Digit Verification of cas no

The CAS Registry Mumber 95975-55-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,5,9,7 and 5 respectively; the second part has 2 digits, 5 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 95975-55:
(7*9)+(6*5)+(5*9)+(4*7)+(3*5)+(2*5)+(1*5)=196
196 % 10 = 6
So 95975-55-6 is a valid CAS Registry Number.
InChI:InChI=1/C21H28O2/c1-4-16-19(23)12-18-15-6-5-13-11-14(22)7-9-20(13,2)17(15)8-10-21(16,18)3/h4,11,15,17-18H,5-10,12H2,1-3H3/b16-4+/t15-,17+,18+,20+,21-/m1/s1

95975-55-6SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name (Z)-Guggulsterone

1.2 Other means of identification

Product number -
Other names GUGGULSTERONE Z

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:95975-55-6 SDS

95975-55-6Synthetic route

5,17(20)-dien-pregna-3,16-diol
672308-23-5

5,17(20)-dien-pregna-3,16-diol

pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

Conditions
ConditionsYield
Stage #1: 5,17(20)-dien-pregna-3,16-diol With aluminum isopropoxide In cyclohexanone; toluene for 4h; Heating / reflux;
Stage #2: With sulfuric acid In cyclohexane; water; toluene		50%
2-ethyl-2-methyl-1,3-dioxolane
126-39-6

2-ethyl-2-methyl-1,3-dioxolane

pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

3,3-ethylenedioxypregna-5,17(20)-dien-16-one
115040-30-7, 115040-31-8

3,3-ethylenedioxypregna-5,17(20)-dien-16-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid at 110℃; for 6h;84%
pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

17α-hydroxy-16α-methylpregn-4-ene-3,20-dione
2868-02-2

17α-hydroxy-16α-methylpregn-4-ene-3,20-dione

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 40 percent / tetrahydrofuran / 24 h / Heating
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
6: 96 percent / 30percent aq H2O2, 10percent aq NaOH / CH2Cl2; aq. ethanol / 48 h / 25 - 32 °C
7: 75 percent / LAH / tetrahydrofuran / 7 h / Heating
8: 0.95 g / 1) oxalyl chloride, DMSO, 2) triethylamine / CH2Cl2 / 2 h / -60 °C
9: 100 percent / p-toluenesulfonic acid / acetone / 15 h / 25 - 30 °C
View Scheme
Multi-step reaction with 9 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 90 percent / TMEDA / diethyl ether / 3 h / Ambient temperature
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
6: 96 percent / 30percent aq H2O2, 10percent aq NaOH / CH2Cl2; aq. ethanol / 48 h / 25 - 32 °C
7: 75 percent / LAH / tetrahydrofuran / 7 h / Heating
8: 0.95 g / 1) oxalyl chloride, DMSO, 2) triethylamine / CH2Cl2 / 2 h / -60 °C
9: 100 percent / p-toluenesulfonic acid / acetone / 15 h / 25 - 30 °C
View Scheme
pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

3,3-ethylenedioxy-16α-methylpregn-5-ene-17α,20ξ-diol
115040-40-9

3,3-ethylenedioxy-16α-methylpregn-5-ene-17α,20ξ-diol

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 40 percent / tetrahydrofuran / 24 h / Heating
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
6: 96 percent / 30percent aq H2O2, 10percent aq NaOH / CH2Cl2; aq. ethanol / 48 h / 25 - 32 °C
7: 75 percent / LAH / tetrahydrofuran / 7 h / Heating
View Scheme
Multi-step reaction with 7 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 90 percent / TMEDA / diethyl ether / 3 h / Ambient temperature
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
6: 96 percent / 30percent aq H2O2, 10percent aq NaOH / CH2Cl2; aq. ethanol / 48 h / 25 - 32 °C
7: 75 percent / LAH / tetrahydrofuran / 7 h / Heating
View Scheme
pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

3,3-ethylenedioxy-16-methylpregna-5,16-dien-20-ol
115040-36-3, 115040-37-4

3,3-ethylenedioxy-16-methylpregna-5,16-dien-20-ol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 40 percent / tetrahydrofuran / 24 h / Heating
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
View Scheme
Multi-step reaction with 4 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 90 percent / TMEDA / diethyl ether / 3 h / Ambient temperature
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
View Scheme
pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

3,3-ethylenedioxy-17,20-epoxy-16α-methylpregna-5-en-16-ol
115040-33-0

3,3-ethylenedioxy-17,20-epoxy-16α-methylpregna-5-en-16-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 40 percent / tetrahydrofuran / 24 h / Heating
3: 40 mg / Jones / acetone / 0.08 h / -15 °C
View Scheme
Multi-step reaction with 3 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 90 percent / TMEDA / diethyl ether / 3 h / Ambient temperature
3: 40 mg / Jones / acetone / 0.08 h / -15 °C
View Scheme
pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

3,3-ethylenedioxy-16-methylpregna-5,16-dien-20-one
115040-38-5

3,3-ethylenedioxy-16-methylpregna-5,16-dien-20-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 40 percent / tetrahydrofuran / 24 h / Heating
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
View Scheme
Multi-step reaction with 5 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 90 percent / TMEDA / diethyl ether / 3 h / Ambient temperature
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
View Scheme
pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

3,3-ethylenedioxy-17α-hydroxy-16α-methylpregn-5-en-20-one
115040-41-0

3,3-ethylenedioxy-17α-hydroxy-16α-methylpregn-5-en-20-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 40 percent / tetrahydrofuran / 24 h / Heating
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
6: 96 percent / 30percent aq H2O2, 10percent aq NaOH / CH2Cl2; aq. ethanol / 48 h / 25 - 32 °C
7: 75 percent / LAH / tetrahydrofuran / 7 h / Heating
8: 0.95 g / 1) oxalyl chloride, DMSO, 2) triethylamine / CH2Cl2 / 2 h / -60 °C
View Scheme
Multi-step reaction with 8 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 90 percent / TMEDA / diethyl ether / 3 h / Ambient temperature
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
6: 96 percent / 30percent aq H2O2, 10percent aq NaOH / CH2Cl2; aq. ethanol / 48 h / 25 - 32 °C
7: 75 percent / LAH / tetrahydrofuran / 7 h / Heating
8: 0.95 g / 1) oxalyl chloride, DMSO, 2) triethylamine / CH2Cl2 / 2 h / -60 °C
View Scheme
pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

3,3-ethylenedioxy-16α,17α-epoxy-16β-methylpregn-5-en-20-one
115040-39-6

3,3-ethylenedioxy-16α,17α-epoxy-16β-methylpregn-5-en-20-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 40 percent / tetrahydrofuran / 24 h / Heating
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
6: 96 percent / 30percent aq H2O2, 10percent aq NaOH / CH2Cl2; aq. ethanol / 48 h / 25 - 32 °C
View Scheme
Multi-step reaction with 6 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 90 percent / TMEDA / diethyl ether / 3 h / Ambient temperature
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
6: 96 percent / 30percent aq H2O2, 10percent aq NaOH / CH2Cl2; aq. ethanol / 48 h / 25 - 32 °C
View Scheme
pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

1-((8R,9S,10R,13S,14S,16R,17R)-17-Hydroxy-10,13,16-trimethyl-3-pyrrolidin-1-yl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone
96764-60-2

1-((8R,9S,10R,13S,14S,16R,17R)-17-Hydroxy-10,13,16-trimethyl-3-pyrrolidin-1-yl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethanone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 40 percent / tetrahydrofuran / 24 h / Heating
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
6: 96 percent / 30percent aq H2O2, 10percent aq NaOH / CH2Cl2; aq. ethanol / 48 h / 25 - 32 °C
7: 75 percent / LAH / tetrahydrofuran / 7 h / Heating
8: 0.95 g / 1) oxalyl chloride, DMSO, 2) triethylamine / CH2Cl2 / 2 h / -60 °C
9: 100 percent / p-toluenesulfonic acid / acetone / 15 h / 25 - 30 °C
10: 92 percent / propan-2-ol / 1 h / Heating
View Scheme
Multi-step reaction with 10 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 90 percent / TMEDA / diethyl ether / 3 h / Ambient temperature
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
4: 5percent KOH / ethanol / 4 h / Heating
5: 197 mg / pyridinium chlorochromate / CH2Cl2 / 1 h / 30 °C
6: 96 percent / 30percent aq H2O2, 10percent aq NaOH / CH2Cl2; aq. ethanol / 48 h / 25 - 32 °C
7: 75 percent / LAH / tetrahydrofuran / 7 h / Heating
8: 0.95 g / 1) oxalyl chloride, DMSO, 2) triethylamine / CH2Cl2 / 2 h / -60 °C
9: 100 percent / p-toluenesulfonic acid / acetone / 15 h / 25 - 30 °C
10: 92 percent / propan-2-ol / 1 h / Heating
View Scheme
pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

3,3-ethylenedioxy-16-methylpregna-5,16-diene-20-acetate
115040-34-1, 115040-35-2

3,3-ethylenedioxy-16-methylpregna-5,16-diene-20-acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 40 percent / tetrahydrofuran / 24 h / Heating
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
View Scheme
Multi-step reaction with 3 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 90 percent / TMEDA / diethyl ether / 3 h / Ambient temperature
3: 80 percent / p-toluenesulfonic acid, acetic acid / CH2Cl2 / 0.33 h / -10 °C
View Scheme
pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

3,3-ethylenedioxy-16α-methylpregna-5,17(20)-dien-16-ol
115059-20-6

3,3-ethylenedioxy-16α-methylpregna-5,17(20)-dien-16-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 40 percent / tetrahydrofuran / 24 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: 84 percent / p-toluenesulfonic acid / 6 h / 110 °C
2: 90 percent / TMEDA / diethyl ether / 3 h / Ambient temperature
View Scheme
pregna-4,17-diene-3,16-dione
95975-55-6

pregna-4,17-diene-3,16-dione

4,17(20)-pregnadiene-3,16-diol
1283145-94-7

4,17(20)-pregnadiene-3,16-diol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 25℃; for 4.5h;30.26 g

95975-55-6Relevant articles and documents

Process for the synthesis of pharmacologically active (z/e)-guggulsterones

-

Page/Page column 2, (2008/06/13)

The invention relates to an improved process for producing pharmacologically active synthetic stereoisomeric mixture of guggulsterones (4) in the three steps. The mixture of gugguisterones consists of Z-guggulsterone [4,17(20)-trans-pregnadiene-3,16-dione] and E-guggulsterone [4,17(20)-cis-pregnadiene-3,16-dione] and could be in any relative ratio. This improved process comprises (a) epoxidation of 16-dehydropregnanolone acetate (1) with hydrogen peroxide (b) reduction of the so obtained epoxide (2) with hydrazine hydrate and (c) oxidation of the diol (3).

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