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95975-55-6

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Basic Information
CAS No.: 95975-55-6
Name: (Z)-Guggulsterone
Article Data: 3
Molecular Structure:
Molecular Structure of 95975-55-6 ((Z)-Guggulsterone)
Formula: C21H28O2
Molecular Weight: 312.452
Synonyms: Guggulsterone;Guglip;Gugulipid;Z/E-Guggulsterone;
EINECS: 1308068-626-2
Density: 1.1 g/cm3
Boiling Point: 463.3 °C at 760 mmHg
Flash Point: 172.3 °C
Solubility: DMSO: 5 mg/mL
Appearance: Light yellow powder
Hazard Symbols: IrritantXi
Risk Codes: 37
Safety: 36
PSA: 34.14000
LogP: 4.64360
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Synthetic route
672308-23-5

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

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%
126-39-6

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

95975-55-6

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

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%
95975-55-6

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

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

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
95975-55-6

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

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
95975-55-6

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

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
95975-55-6

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

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
95975-55-6

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

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
95975-55-6

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

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
95975-55-6

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

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
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Chemistry

Molecular Structure of Pregna-4,17(20)-diene-3,16-dione (CAS NO.95975-55-6):

Molecular Formula: C21H28O2
Molecular Weight: 312.4458
IUPAC Name: (8R,9S,10R,13S,14S,17E)-17-Ethylidene-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthrene-3,16-dione
Synonyms of Pregna-4,17(20)-diene-3,16-dione (CAS NO.95975-55-6): (Z)-Guggulsterone ; Guggulsterone ; (17E)-Pregna-4,17(20)-diene-3,16-dione
CAS NO: 95975-55-6
Classification Code: Miscellaneous 
Index of Refraction: 1.557
Molar Refractivity: 90.65 cm3
Molar Volume: 281.5 cm3
Surface Tension: 42.2 dyne/cm
Density: 1.1 g/cm3
Flash Point: 172.3 °C
Enthalpy of Vaporization: 72.45 kJ/mol
Boiling Point: 463.3 °C at 760 mmHg
Vapour Pressure: 9.21E-09 mmHg at 25°C

Safety Profile

Hazard Codes of Pregna-4,17(20)-diene-3,16-dione (CAS NO.95975-55-6): IrritantXi
Risk Statements: 37 
R37: Irritating to respiratory system
Safety Statements: 36 
S36: Wear suitable protective clothing.
WGK Germany: 3