Brusatol supplier | CasNO.14907-98-3

Name
brusatol
EINECS
CAS No. 14907-98-3
Article Data5
CAS DataBase
Density 1.46g/cm³
Solubility
Melting Point
Formula C26H32 O11
Boiling Point 724.3°Cat760mmHg
Molecular Weight 520.533
Flash Point 242.2°C
Transport Information
Appearance
Safety Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.
Risk Codes
Molecular Structure
Hazard Symbols
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
PSA 165.89000
LogP 0.51700

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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;	50%

: C19H16N2O9S

: 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

: C45H46N2O19S

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;	47.4%

: 1186196-66-6
4-(2-(2-((3-carboxypropanoyl)oxy)ethoxy)ethoxy)-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

: C42H48N2O20S

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;	47.2%

: C19H16N2O9S

: 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

: C45H46N2O19S

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;	46.2%

: 1236876-86-0
4-((4-((3-carboxypropanoyl)oxy)but-2-yn-1-yl)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

: C42H44N2O19S

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;	45%

: 1314187-65-9
C13H12N2O6

: 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

: C39H42N2O16

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;	41.8%

: 80-48-8
methyl p-toluene sulfonate

: 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

: 3-O-methylbrusatol

Conditions

Conditions	Yield
With potassium carbonate In acetone at 50℃; for 168h;	37%

: 14794-31-1
ethyl 3-(chloroformyl)propionate

: 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

: 81681-67-6
brusatol-3-yl ethyl succinate

Conditions

Conditions	Yield
With pyridine In chloroform at 24℃; for 17h; Acylation;	32%

: 1393477-75-2
4-(4-((3-carboxypropanoyl)oxy)n-propoxy)-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

: C41H46N2O19S

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;	32%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 51h; Cooling with ice;	32%

: 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

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;	30.7%
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 51h; Cooling with ice;	30.7%

: C17H12N2O6

: 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

: C43H42N2O16

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;	30.5%

: 1393477-81-0
C20H18N2O9S

: 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

: C46H48N2O19S

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Heating;	25%

: 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

: 888483-24-7
C26H30O10

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 55 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / 20 °C 2: 90 percent / triethylamine; 4-(dimethylamino)pyridine / dioxane / 1 h / 20 °C 3: 87 percent / triethylamine; formic acid / palladium(II) acetate; 1,1'-bis(diphynylphosphino)ferrocene / dimethylformamide / 1 h / 50 °C View Scheme

: 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

: C26H32O10

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 75 percent / triethylamine; 4-(dimethylamino)pyridine / dioxane / 0.5 h / 20 °C 2: 68 percent / triethylamine; formic acid / palladium(II) acetate; 1,1'-bis(diphenylphosphino)ferrocene / dimethylformamide / 2 h / 45 °C View Scheme

: 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

: C26H32O10

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 55 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / 20 °C 2: 90 percent / triethylamine; 4-(dimethylamino)pyridine / dioxane / 1 h / 20 °C 3: 87 percent / triethylamine; formic acid / palladium(II) acetate; 1,1'-bis(diphynylphosphino)ferrocene / dimethylformamide / 1 h / 50 °C 4: 62 percent / hydrogen / tris(triphenylphosphine)rhodium(I) chloride / benzene / 30 h / 45 °C View Scheme

Yield

Multi-step reaction with 4 steps
1: 55 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / dioxane / 1 h / 20 °C
2: 90 percent / triethylamine; 4-(dimethylamino)pyridine / dioxane / 1 h / 20 °C
3: 87 percent / triethylamine; formic acid / palladium(II) acetate; 1,1'-bis(diphynylphosphino)ferrocene / dimethylformamide / 1 h / 50 °C
4: 62 percent / hydrogen / tris(triphenylphosphine)rhodium(I) chloride / benzene / 30 h / 45 °C
View Scheme

: 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

: C26H30O11

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 91 percent / imidazole / dimethylformamide / 24 h / 20 °C 2: 77 percent / chromium(VI) oxide; sulfuric acid / acetone; H2O / 1 h / 20 °C 3: 46 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C View Scheme

: 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

: C27H34O11

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 91 percent / imidazole / dimethylformamide / 24 h / 20 °C 2: 72 percent / lithium iodide; pyridine / 24 h / 100 °C 3: 90 percent / potassium carbonate / acetone / 6 h / 50 °C 4: 76 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C View Scheme

: 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

: C32H43ClO9Si

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / imidazole / dimethylformamide / 24 h / 20 °C 2: 25 percent / thionyl chloride; pyridine / CHCl3 / 0 - 60 °C View Scheme

: 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

: C32H43ClO9Si

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 91 percent / imidazole / dimethylformamide / 24 h / 20 °C 2: 54 percent / thionyl chloride; pyridine / CHCl3 / 0 - 60 °C View Scheme

: 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

: C28H36O11

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 91 percent / imidazole / dimethylformamide / 24 h / 20 °C 2: 72 percent / lithium iodide; pyridine / 24 h / 100 °C 3: 91 percent / potassium carbonate / acetone / 16 h / 50 °C 4: 79 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C View Scheme

: 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

: C29H38O11

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 91 percent / imidazole / dimethylformamide / 24 h / 20 °C 2: 72 percent / lithium iodide; pyridine / 24 h / 100 °C 3: 92 percent / potassium carbonate / acetone / 16 h / 50 °C 4: 73 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C View Scheme

Brusatol Chemical Properties

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):

Brusatol 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.

Brusatol Safety Profile

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

Brusatol 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 .

Product Name

brusatol

Synthetic route

Brusatol Chemical Properties

Brusatol Toxicity Data With Reference

Brusatol Safety Profile

Brusatol Specification

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