Troglitazone supplier | CasNO.97322-87-7

Name
Troglitazone
EINECS
CAS No. 97322-87-7
Article Data6
CAS DataBase
Density 1.266 g/cm³
Solubility
Melting Point 184-186 °C
Formula C₂₄H₂₇NO₅S
Boiling Point 657 °C at 760 mmHg
Molecular Weight 441.548
Flash Point 351.2 °C
Transport Information
Appearance crystalline solid
Safety 22-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms CI 991;CS045;Depotox;GR 92132X;Noscal;Rezulin;Romglizone;
PSA 110.16000
LogP 4.70300

Synthetic route

: 5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-yl-methoxy)benzylidene]-2,4-thiazolidinedione

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
With sodium tetrahydroborate; dimethylaminoacetic acid; sodium hydroxide In tetrahydrofuran; water at 20℃;	84%
With hydrogen; acetic acid In water; palladium

: 199441-78-6
5-[4-(6-benzyloxy-2,5,7,8-tetramethyl-chroman-2-ylmethoxy)-benzyl]-thiazolidine-2,4-dione

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid at 70 - 80℃; debenzylation;	70%

: 17356-08-0
thiourea

: 97322-68-4
Ethyl 3-<4-<(6-acetoxy-2,5,7,8-tetramethylchroman-2-yl)methoxy>phenyl>-2-chloropropionate

A: 97322-87-7
Troglitazone

B: 97323-08-5
5-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]-2-iminothiazolidin-4-one

Conditions

Conditions	Yield
With hydrogenchloride; acetic acid 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 127040-01-1
Troglitazone glucuronide

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
enzymatic treatment using glusulase;

: 459-57-4
4-fluorobenzaldehyde

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium tert-butoxide / dimethylformamide / 8 h / 80 °C 2: AcOH; piperidine / toluene / 4 h / Heating 3: HCl / methanol / 0.25 h 4: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C View Scheme

: 56305-04-5, 53188-07-1
trolox

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: imidazole / dimethylformamide 2: LAH / 3 h / 20 °C 3: potassium tert-butoxide / dimethylformamide / 8 h / 80 °C 4: AcOH; piperidine / toluene / 4 h / Heating 5: HCl / methanol / 0.25 h 6: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C View Scheme
Multi-step reaction with 8 steps 1: toluene-4-sulfonic acid / 12 h / Reflux 2: dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere 3: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 4: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 5: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere 6: piperidine / ethanol / 12 h / Inert atmosphere; Reflux 7: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr 8: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1: imidazole / dimethylformamide
2: LAH / 3 h / 20 °C
3: potassium tert-butoxide / dimethylformamide / 8 h / 80 °C
4: AcOH; piperidine / toluene / 4 h / Heating
5: HCl / methanol / 0.25 h
6: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C
View Scheme

Multi-step reaction with 8 steps
1: toluene-4-sulfonic acid / 12 h / Reflux
2: dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere
3: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
4: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
5: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere
6: piperidine / ethanol / 12 h / Inert atmosphere; Reflux
7: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr
8: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux
View Scheme

: 228114-44-1
(6-t-butyldimethylsilyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzo[1,2-b]pyran-2yl)methanol

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium tert-butoxide / dimethylformamide / 8 h / 80 °C 2: AcOH; piperidine / toluene / 4 h / Heating 3: HCl / methanol / 0.25 h 4: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C View Scheme

: 716320-66-0
6-tert-butyl(dimethyl)silyloxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-1-benzopyran-2-carboxylic acid

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: LAH / 3 h / 20 °C 2: potassium tert-butoxide / dimethylformamide / 8 h / 80 °C 3: AcOH; piperidine / toluene / 4 h / Heating 4: HCl / methanol / 0.25 h 5: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C View Scheme

: 716320-67-1
4-[6-(tert-butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethyl-chroman-2-ylmethoxy]-benzaldehyde

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: AcOH; piperidine / toluene / 4 h / Heating 2: HCl / methanol / 0.25 h 3: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C View Scheme

: 5-[1-{4-[6-(tert-Butyl-dimethyl-silanyloxy)-2,5,7,8-tetramethyl-chroman-2-ylmethoxy]-phenyl}-meth-(E)-ylidene]-thiazolidine-2,4-dione

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: HCl / methanol / 0.25 h 2: 84 percent / CoCl2; DMG; NaBH4 / NaOH / tetrahydrofuran; H2O / 20 °C View Scheme

: 459-57-4
4-fluorobenzaldehyde

A: 97322-87-7
Troglitazone

B PhCO-X: PhCO-X

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: t-BuOK / dimethylformamide / 1 h / 25 °C 1.2: 60 percent / dimethylformamide / 15 h / 25 °C 2.1: benzoic acid; piperidine / toluene / 4 h / 120 °C 3.1: 54 percent / Mg; MeOH / 8 h / 45 °C 4.1: 70 percent / HCl; AcOH / 70 - 80 °C View Scheme

: 171270-07-8
(6-Benzyloxy-3,4-dihydro-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methanol

A: 97322-87-7
Troglitazone

B PhCO-X: PhCO-X

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: t-BuOK / dimethylformamide / 1 h / 25 °C 1.2: 60 percent / dimethylformamide / 15 h / 25 °C 2.1: benzoic acid; piperidine / toluene / 4 h / 120 °C 3.1: 54 percent / Mg; MeOH / 8 h / 45 °C 4.1: 70 percent / HCl; AcOH / 70 - 80 °C View Scheme

: 138564-69-9
4-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy]benzaldehyde

A: 97322-87-7
Troglitazone

B PhCO-X: PhCO-X

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: benzoic acid; piperidine / toluene / 4 h / 120 °C 2: 54 percent / Mg; MeOH / 8 h / 45 °C 3: 70 percent / HCl; AcOH / 70 - 80 °C View Scheme

: 906357-28-6
TG-12

A: 97322-87-7
Troglitazone

B PhCO-X: PhCO-X

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 54 percent / Mg; MeOH / 8 h / 45 °C 2: 70 percent / HCl; AcOH / 70 - 80 °C View Scheme

: 79907-49-6
2-hydroxymethyl-2,5,7,8-tetramethyl-chroman-6-ol

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: 1.) NaH / 1.) DMF, rt, 1 h, 2.) benzene, rt, 1 h 2: 1.) NaH / 1.) DMSO, benzene, 60 deg C, 20 min, 2.) 60 deg C, 1 h 3: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C 4: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h 5: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr 6: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 7: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

Yield

Multi-step reaction with 7 steps
1: 1.) NaH / 1.) DMF, rt, 1 h, 2.) benzene, rt, 1 h
2: 1.) NaH / 1.) DMSO, benzene, 60 deg C, 20 min, 2.) 60 deg C, 1 h
3: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C
4: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h
5: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr
6: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min
7: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h
View Scheme

: 107188-55-6
2-hydroxymethyl-6-methoxymethoxy-2,5,7,8-tetramethylchroman

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 1.) NaH / 1.) DMSO, benzene, 60 deg C, 20 min, 2.) 60 deg C, 1 h 2: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C 3: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h 4: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr 5: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 6: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

Yield

Multi-step reaction with 6 steps
1: 1.) NaH / 1.) DMSO, benzene, 60 deg C, 20 min, 2.) 60 deg C, 1 h
2: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C
3: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h
4: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr
5: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min
6: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h
View Scheme

: 107188-58-9
6-Hydroxy-2,5,7,8-tetramethyl-2-<(4-nitrophenoxy)methyl>chroman

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h 2: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr 3: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 4: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

: 107188-37-4
6-acetoxy-2-[(4-aminophenoxy)methyl]-2,5,7,8-tetramethylchromane

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 2: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

: 118070-83-0
2,5,7,8-tetramethyl-6-acetoxy-2-(4-nitrophenyloxy)methylchroman

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr 2: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 3: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

: 118070-84-1
6-(Methoxymethoxy)-2,5,7,8-tetramethyl-2-<(4-nitrophenoxy)methyl>chroman

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C 2: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h 3: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr 4: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min 5: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h View Scheme

Yield

Multi-step reaction with 5 steps
1: 94 percent / AcOH, 10percent H2SO4 / 0.17 h / 60 °C
2: 94 percent / pyridine / 1.) 10 deg C to rt, 2.) 30 deg C, 1 h
3: 98 percent / H2 / 10percent Pd-C / methanol; benzene / 3 h / 2325.2 - 2850.2 Torr
4: 1.) aq. NaNO2, conc. HCl, 2.) Cu2O / 1.) acetone, 0 deg C, 2.) 40 to 43 deg C, 30 min
5: 2.) AcOH, conc. HCl / 1.) sulfolane, 115 to 120 deg C, 80 min, 2.) H2O, 85 to 90 deg c, 12 h
View Scheme

: 107187-56-4
(+/-)-5-<4-(6-hydroxy-2,5,7,8-tetramethyl-2H-chromen-2-ylmethoxy)benzyl>thiazolidine-2,4-dione

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
In methanol; palladium

: 109-86-4
2-methoxy-ethanol

: 97322-68-4
Ethyl 3-<4-<(6-acetoxy-2,5,7,8-tetramethylchroman-2-yl)methoxy>phenyl>-2-chloropropionate

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
With hydrogenchloride; thiourea In sulfolane

: 1375483-15-0
carbonic acid tert-butyl ester 2-{4-[2,4-dioxo-thiazolidin-(5Z)-ylidenemethyl]phenoxymethyl}-2,5,7,8-tetramethyl-chroman-6-yl ester

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr 2: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux View Scheme

: 1375483-24-1
carbonic acid tert-butyl ester 2-{4-[2,4-dioxothiazolidin-5-ylmethyl]phenoxymethyl}-2,5,7,8-tetramethylchroman-6-yl ester

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
With hydrogenchloride; water In acetonitrile for 0.75h; Reflux;

: C20H27F3O7S

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere 2: piperidine / ethanol / 12 h / Inert atmosphere; Reflux 3: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr 4: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux View Scheme

: 1375483-09-2
6-tert-butoxycarbonyloxy-2,5,7,8-tetramethyl-chroman-2-carboxylic acid ethyl ester

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 3: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere 4: piperidine / ethanol / 12 h / Inert atmosphere; Reflux 5: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr 6: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
2: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
3: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere
4: piperidine / ethanol / 12 h / Inert atmosphere; Reflux
5: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr
6: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux
View Scheme

: 1375483-11-6
carbonic acid tert-butyl ester 2-hydroxymethyl-2,5,7,8-tetramethyl-chroman-6-yl ester

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 2: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere 3: piperidine / ethanol / 12 h / Inert atmosphere; Reflux 4: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr 5: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux View Scheme

Yield

Multi-step reaction with 5 steps
1: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
2: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere
3: piperidine / ethanol / 12 h / Inert atmosphere; Reflux
4: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr
5: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux
View Scheme

: 1375483-13-8
carbonic acid tert-butyl ester 2-(4-formylphenoxymethyl)-2,5,7,8-tetramethyl-chroman-6-yl ester

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: piperidine / ethanol / 12 h / Inert atmosphere; Reflux 2: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr 3: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux View Scheme

: 53174-07-5
ethyl 6-hydroxy-2,5,7,8-tetramethyl-3,4-dihydro-2H-chromene-2-carboxylate

: 97322-87-7
Troglitazone

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1: dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere 2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 3: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere 4: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere 5: piperidine / ethanol / 12 h / Inert atmosphere; Reflux 6: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr 7: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux View Scheme

Yield

Multi-step reaction with 7 steps
1: dmap / dichloromethane / 2 h / 20 °C / Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
3: pyridine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
4: potassium carbonate / N,N-dimethyl-formamide / 48 h / 2 °C / Inert atmosphere
5: piperidine / ethanol / 12 h / Inert atmosphere; Reflux
6: palladium 10% on activated carbon; hydrogen / 1,4-dioxane / 20 h / 20 °C / 3620.13 Torr
7: hydrogenchloride; water / acetonitrile / 0.75 h / Reflux
View Scheme

: 108-24-7
acetic anhydride

: 97322-87-7
Troglitazone

: 71-43-2
benzene

: 5-<4-<(6-Acetoxy-2,5,7,8-tetramethylchroman-2-yl)methoxy>benzyl>-2,4-thiazolidinedione benzene monoadduct

Conditions

Conditions	Yield
With pyridine for 48h; Ambient temperature;	80%

...Expand

: 97322-87-7
Troglitazone

3-PyCO-X: 3-PyCO-X

: 97323-02-9
5-[4-(2,5,7,8-tetramethyl-6-nicotinoyloxychroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

Conditions

Conditions	Yield
	75%

: 108-30-5
succinic acid anhydride

: 97322-87-7
Troglitazone

: succinic acid mono-{2-[4-(2,4-dioxo-thiazolidin-5-ylmethyl)-phenoxymethyl]-2,5,7,8-tetramethyl-chroman-6-yl} ester

Conditions

Conditions	Yield
With dmap In dichloromethane for 48h; Reflux;	63%
With pyridine at 85℃; for 6h;
With pyridine In cyclohexane

: 97322-87-7
Troglitazone

PhCO-X: PhCO-X

: 97323-01-8
5-[4-(6-benzoyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

Conditions

Conditions	Yield
	62%

: 97322-87-7
Troglitazone

PrCO-X: PrCO-X

: 97323-00-7
5-[4-(6-butyryloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

Conditions

Conditions	Yield
	56%

: 97322-87-7
Troglitazone

: 7355-18-2
(2S,3S,4S,5R,6S)-3,4,5,6-Tetraacetoxy-tetrahydro-pyran-2-carboxylic acid methyl ester

: 127040-00-0
methyl 2,3,4-tri-O-acetyl-1-O-<2-<4-<2,4-dioxothiazolidin-5-ylmethyl>phenoxymethyl>-2,5,7,8-tetramethylchroman-6-yl>-β-D-glucopyranuronate

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In nitrobenzene at 85℃; under 20 Torr; for 4h;	23%

: 97322-87-7
Troglitazone

: 127040-01-1
Troglitazone glucuronide

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 23 percent / p-toluenesulfonic acid monohydrate / nitrobenzene / 4 h / 85 °C / 20 Torr 2: 100 percent / 2.4percent aq.NaOH / methanol / 1 h / Ambient temperature View Scheme

: 5292-43-3
bromoacetic acid tert-butyl ester

: 97322-87-7
Troglitazone

: 107187-69-9
Di-t-butyl α,α'-{5-[4-(6-t-butoxycarbonylmethoxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl ]-2,4-dioxothiazolidine-3,5-diyl}diacetate

Conditions

Conditions	Yield
With potassium carbonate In acetone

Troglitazone Chemical Properties

Product Name: Troglitazone (CAS NO.97322-87-7)

Molecular Formula: C₂₄H₂₇NO₅S
Molecular Weight: 441.54g/mol
Mol File: 97322-87-7.mol
Appearance: Crystalline Solid
Melting Point: 184-186°C
Boiling point: 657 °C at 760 mmHg
Flash Point: 351.2 °C
Density: 1.266 g/cm³
Surface Tension: 51 dyne/cm
Enthalpy of Vaporization: 100.24 kJ/mol
Vapour Pressure: 7.24E-18 mmHg at 25°C
XLogP3-AA: 5.1
H-Bond Donor: 2
H-Bond Acceptor: 5
Structure Descriptors of Troglitazone (CAS NO.97322-87-7):
IUPAC Name: 5-[[4-[(6-hydroxy-2,5,7,8-tetramethyl-3,
4-dihydrochromen-2-yl)methoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
Canonical SMILES: CC1=C(C(=C2CCC(OC2=C1C)(C)COC3=CC=C(C=C3)CC4C(=O)NC(=O)S4)C)O
InChI: InChI=1S/C24H27NO5S/c1-13-14(2)21-18(15(3)20(13)26)9-10-24(4,
30-21)12-29-17-7-5-16(6-8-17)11-19-22(27)25-23(28)31-19/h5-8,19,26H,
9-12H2,1-4H3,(H,25,27,28)
InChIKey: GXPHKUHSUJUWKP-UHFFFAOYSA-N
Product Categories: Active Pharmaceutical Ingredients; Intermediates & Fine Chemicals; Pharmaceuticals; Intracellular receptor

Troglitazone Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
monkey	LD50	oral	> 2gm/kg (2000mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 38, Pg. 1121, 1996.
mouse	LD	oral	> 300mg/kg (300mg/kg)		European Patent Application. Vol. #439321,
mouse	LD50	intraperitoneal	> 5gm/kg (5000mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
mouse	LD50	intravenous	42mg/kg (42mg/kg)		Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
rat	LD50	intraperitoneal	> 4gm/kg (4000mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
rat	LD50	oral	> 5gm/kg (5000mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 26, Pg. 953, 1995.
women	TDLo	oral	840mg/kg/15W- (840mg/kg)	BRAIN AND COVERINGS: ENCEPHALITIS LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE" LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"	Annals of Internal Medicine. Vol. 129, Pg. 98, 1998.

Troglitazone Safety Profile

Safety Information of Troglitazone (CAS NO.97322-87-7):
Safety Statements: 22-24/25
22: Do not breathe dust
24: Avoid contact with skin
25: Avoid contact with eyes

Troglitazone Specification

Troglitazone ,its CAS NO. is 97322-87-7,the synonyms is (+-)-all-rac-5-(p-((6-Hydroxy-2,5,7,8-tetramethyl-2-chromanyl)methoxy)benzyl)-2,4-thiazolidinedione ; 2,4-Thiazolidinedione, 5-((4-((3,4-dihydro-6-hydroxy-2,5,7,8-tetramethyl-2H-1-benzopyran-2-yl)methoxy)phenyl)methyl)- ; 5-(4-(6-Hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl)thiazolidine-2,4-dione ; BRN 4338399 ; CCRIS 8969 ; CI 991 ; CS 045 ; GR 92132X ; Prelay ; Rezulin ; Romglizone ; UNII-I66ZZ0ZN0E .

Product Name

Troglitazone

Synthetic route

Troglitazone Chemical Properties

Troglitazone Toxicity Data With Reference

Troglitazone Safety Profile

Troglitazone Specification

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