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Basic Information
CAS No.: 14907-98-3
Name: brusatol
Molecular Structure:
Molecular Structure of 14907-98-3 (brusatol)
Formula: C26H32 O11
Molecular Weight: 520.533
Synonyms: 2H-3,11cb-(Epoxymethano)phenanthro[10,1-bc]pyran-3a(3abH)-carboxylic acid, 1,4,5,6ab,7,7aa,10,11,11a,11ba-decahydro-1b,2a,4b,9-tetrahydroxy-8,11ab-dimethyl-5,10-dioxo-, methylester, 4-(3-methylcrotonate) (8CI); Picras-3-en-21-oic acid,13,20-epoxy-3,11,12-trihydroxy-15-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxo-,methyl ester, (11b,12a,15b)- (9CI); Crotonic acid, 3-methyl-, 4-ester withmethyl 1,4,5,6ab,7,7aa,10,11,11a,11ba-decahydro-1b,2a,4b,9-tetrahydroxy-8,11ab-dimethyl-5,10-dioxo-2H-3,11cb-(epoxymethano)phenanthro[10,1-bc]pyran-3a(3abH)-carboxylate (8CI); (+)-Brusatol; Brusatol; NSC 172924; Yatansin
Density: 1.46g/cm3
Boiling Point: 724.3°Cat760mmHg
Flash Point: 242.2°C
Safety: Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
PSA: 165.89000
LogP: 0.51700
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Synthetic route
67-56-1

methanol

bruceoside D

14907-98-3

13,20-epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 20h; methanolysis; Heating;48.8%
18162-48-6

tert-butyldimethylsilyl chloride

14907-98-3

13,20-epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester

92116-31-9

3-(tert-butyldimethylsilyl)-brusatol

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h;91%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 45℃; for 3h;89.6%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃;
37595-74-7

N,N-phenylbistrifluoromethane-sulfonimide

14907-98-3

13,20-epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester

C27H31F3O13S

Conditions
ConditionsYield
With dmap; triethylamine In 1,4-dioxane at 20℃; for 0.5h;75%

C20H18N2O7

14907-98-3

13,20-epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester

C46H48N2O17

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;70%
1186196-64-4

4-(4-((3-carboxypropanoyl)oxy)n-butoxy)-3-benzenesulfonyl-1,2,5-oxadiazole-2-oxide

14907-98-3

13,20-epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester

C42H48N2O19S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;65.5%
1446816-83-6

4-((5-((3-carboxypropanoyl)oxy)pentyl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide

14907-98-3

13,20-epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester

C43H50N2O19S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;56.5%
14907-98-3

13,20-epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester

99132-98-6

dehydrobrusatol

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane at 20℃; for 1h;55%

C16H13BrN2O3

14907-98-3

13,20-epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester

C42H44N2O14

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 50℃; for 5h; Inert atmosphere;54.2%
With potassium carbonate In acetonitrile at 80℃; for 20h;54.2%

C20H18N2O7

14907-98-3

13,20-epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester

C46H48N2O17

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;51%

4-(4-((3-carboxypropanoyl)oxy)sec-butoxy)-3-benzenesulfonyl-1,2,5-oxadiazole-2-oxide

14907-98-3

13,20-epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicras-3-en-21-oic acid methyl ester

C42H48N2O19S

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;50%
Raw Materials
63306-30-9
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Chemistry

Empirical Formula of Brusatol (CAS NO.14907-98-3): C26H32O11
Molecular Weight: 520.5257 g/mol
Index of Refraction: 1.609
Density: 1.46 g/cm3
Flash Point: 242.2 °C
Enthalpy of Vaporization: 120.81 kJ/mol
Boiling Point: 724.3 °C at 760 mmHg
Vapour Pressure: 3.18E-24 mmHg at 25 °C
Structure of Brusatol (CAS NO.14907-98-3):
            

Toxicity Data With Reference

1.    

dni-mus-lym 15 µmol/L

     JPMSAE    Journal of Pharmaceutical Sciences. 68 (1979),883.
2.    

uns-mus-lym 15 µmol/L

     JPMSAE    Journal of Pharmaceutical Sciences. 68 (1979),883.

Safety Profile

Mutation data reported. When heated to decomposition Brusatol (CAS NO.14907-98-3) emits acrid smoke and irritating vapors.

Specification

 Brusatol ,its cas register number is 14907-98-3. It also can be called Methyl (11beta,12alpha,15beta)-3,11,12-trihydroxy-15-[(3-methylbut-2-enoyl)oxy]-2,16-dioxo-13,20-epoxypicras-3-en-21-oate ; and Yatansin .