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Troglitazone
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Name

Troglitazone

 EINECS N/A
CAS No. 97322-87-7 Density 1.266 g/cm3
PSA 110.16000 LogP 4.70300
Solubility N/A 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 N/A Appearance crystalline solid
Safety 22-24/25 Risk Codes N/A
Molecular Structure Molecular Structure of 97322-87-7 (Troglitazone) Hazard Symbols N/A
Synonyms

CI 991;CS045;Depotox;GR 92132X;Noscal;Rezulin;Romglizone;

Article Data 6

Troglitazone Synthetic route

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

97322-87-7

Troglitazone

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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;
127040-01-1

Troglitazone glucuronide

97322-87-7

Troglitazone

Conditions
ConditionsYield
enzymatic treatment using glusulase;
459-57-4

4-fluorobenzaldehyde

97322-87-7

Troglitazone

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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

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 .

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