14907-98-3

Basic information

• Product Name: brusatol
• Synonyms: 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;13,20-Epoxy-3,11β,12α-trihydroxy-15β-[(3-methyl-1-oxo-2-butenyl)oxy]-2,16-dioxopicrasa-3-ene-21-oic acid methyl ester;Picras-3-en-21-oicacid,13,20-epoxy-3,11,12-trihydroxy-15-[(3-Methyl-1-oxo-2-buten-1-yl)oxy]-2,16-dioxo-,Methyl ester, (11b,12a,15b)-;NSC 172924;Yatansin;Brustaol;Picras-3-en-21-oic acid, 13,20-epoxy-3,11,12-trihydroxy-15-[(3-methyl-1-oxo-2-buten-1-yl)oxy]-
• CAS NO: 14907-98-3
• Molecular Formula: C₂₆H₃₂O₁₁
• Molecular Weight: 520.528
• Mol File: 14907-98-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 724.3°Cat760mmHg
• Flash Point: 242.2°C
• Appearance: /
• Density: 1.46±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 3.18E-24mmHg at 25°C
• Refractive Index: 1.609
• Storage Temp.: -20°C
• PKA: 8.81±0.70(Predicted)
• CAS DataBase Reference: brusatol(CAS DataBase Reference)
• NIST Chemistry Reference: brusatol(14907-98-3)
• EPA Substance Registry System: brusatol(14907-98-3)

Safety Data

• Hazardous Substances Data: 14907-98-3(Hazardous Substances Data)

Usage

Uses

Brusatol has been used to study the protective role of Nrf2 (nuclear factor, erythroid 2 like 2 ) in intestinal ischemia/reperfusion induced injury.

Biochem/physiol Actions

Brusatol promotes Nrf2 (nuclear factor, erythroid 2 like 2 ) ubiquitination and degradation. Brusatol upregulates the expression of multiple ribosomal components and controls macromolecular complex function.

InChI:InChI=1/C26H32O11/c1-10(2)6-15(28)37-18-20-25-9-35-26(20,23(33)34-5)21(31)17(30)19(25)24(4)8-13(27)16(29)11(3)12(24)7-14(25)36-22(18)32/h6,12,14,17-21,29-31H,7-9H2,1-5H3

Synthetic route

methanol (67-56-1) + bruceoside D → 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 (14907-98-3)

Conditions	Yield
With toluene-4-sulfonic acid for 20h; methanolysis; Heating;	48.8%

tert-butyldimethylsilyl chloride (18162-48-6) + 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 (14907-98-3) → 3-(tert-butyldimethylsilyl)-brusatol (92116-31-9)

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℃;

N,N-phenylbistrifluoromethane-sulfonimide (37595-74-7) + 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 (14907-98-3) → C27H31F3O13S

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

C20H18N2O7 + 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 (14907-98-3) → C46H48N2O17

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

4-(4-((3-carboxypropanoyl)oxy)n-butoxy)-3-benzenesulfonyl-1,2,5-oxadiazole-2-oxide (1186196-64-4) + 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 (14907-98-3) → C42H48N2O19S

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

4-((5-((3-carboxypropanoyl)oxy)pentyl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide (1446816-83-6) + 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 (14907-98-3) → C43H50N2O19S

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

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 (14907-98-3) → dehydrobrusatol (99132-98-6)

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

C16H13BrN2O3 + 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 (14907-98-3) → C42H44N2O14

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 + 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 (14907-98-3) → C46H48N2O17

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 + 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 (14907-98-3) → C42H48N2O19S

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

C19H16N2O9S + 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 (14907-98-3) → C45H46N2O19S

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

4-(2-(2-((3-carboxypropanoyl)oxy)ethoxy)ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide (1186196-66-6) + 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 (14907-98-3) → C42H48N2O20S

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

C19H16N2O9S + 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 (14907-98-3) → C45H46N2O19S

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

4-((4-((3-carboxypropanoyl)oxy)but-2-yn-1-yl)oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide (1236876-86-0) + 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 (14907-98-3) → C42H44N2O19S

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

C13H12N2O6 (1314187-65-9) + 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 (14907-98-3) → C39H42N2O16

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

methyl p-toluene sulfonate (80-48-8) + 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 (14907-98-3) → 3-O-methylbrusatol

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

ethyl 3-(chloroformyl)propionate (14794-31-1) + 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 (14907-98-3) → brusatol-3-yl ethyl succinate (81681-67-6)

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

4-(4-((3-carboxypropanoyl)oxy)n-propoxy)-3-benzenesulfonyl-1,2,5-oxadiazole-2-oxide (1393477-75-2) + 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 (14907-98-3) → C41H46N2O19S

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 + 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 (14907-98-3) → C46H48N2O17

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 + 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 (14907-98-3) → C43H42N2O16

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

C20H18N2O9S (1393477-81-0) + 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 (14907-98-3) → C46H48N2O19S

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

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 (14907-98-3) → C26H30O10 (888483-24-7)

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

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 (14907-98-3) → C26H32O10

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

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 (14907-98-3) → C26H32O10

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

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 (14907-98-3) → C26H30O11

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

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 (14907-98-3) → C27H34O11

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

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 (14907-98-3) → C32H43ClO9Si

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

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 (14907-98-3) → C32H43ClO9Si

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

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 (14907-98-3) → C28H36O11

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

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 (14907-98-3) → C29H38O11

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

Upstream product

• 67-56-1 methanol 
• 167782-22-1 bruceoside-D 
• 14907-99-4 11,12-diacetoxybrusatol-3-yl acetate 
• 63306-30-9 bruceoside A 

Downstream Products

• 81617-85-8 bisbrusatolyl glutarate 

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