5-((4-Hydroxyphenyl)methylene)-2,4-thiazolidinedione

HCID 517822

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Basic information

CAS: 103788-60-9
Standard SMILES: O=C1NC(=O)C(=Cc2ccc(O)cc2)S1
InChIKey: ARHIHDVVUHVQCP-UHFFFAOYSA-N
Molecular formula: C10H7NO3S
Average molar mass: 221.23 g/mol

Names & identifiers

Preferred name: 5-((4-Hydroxyphenyl)methylene)-2,4-thiazolidinedione
IUPAC: 5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
English name: 2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]-
Molecular formula: C10H7NO3S
Molecular weight: 221.23

Names & synonyms

103788-60-95-((4-Hydroxyphenyl)methylene)-2,4-thiazolidinedioneRefChem:10723145-(4-hydroxybenzylidene)thiazolidine-2,4-dione5-[(4-hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dioneMFCD00640639154052-92-35-[(E)-(4-hydroxyphenyl)methylidene]-1,3-thiazolane-2,4-dione(Z)-5-(4-Hydroxybenzylidene)thiazolidine-2,4-dioneMFCD007110762,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]-, (5Z)-CBMicro_020528

Show more names

Pioglitazone Impurity 425-(4-hydroxybenzylidene)-2,4-thiazolidinedione5-[(4-hydroxyphenyl)methylene]-2,4-Thiazolidinedione2,4-Thiazolidinedione, 5-[(4-hydroxyphenyl)methylene]-(Z)-5-(4-hydroxybenzylidene)thiazolidine-2,4-dione(WX180325)Pioglitazone impurity 5-(4-Hydroxybenzylidene)thiazolidine-2,4-dione

SCHEMBL621991SCHEMBL4862901ARHIHDVVUHVQCP-UHFFFAOYSA-NHMS3380A10AKOS030240083SY129798DB-059050W15187

Database identifiers

CAS: 103788-60-9
PubChem CID: 517822
EC Number: 104-841-5

Properties

Computed structural properties

XLogP: 1.8
Topological polar surface area: 91.7 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 1
Heavy atoms: 15
Formal charge: 0
Complexity: 319

Physicochemical properties

HazardClass: IRRITANT

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesEye Irrit. 2 (100%)

Safety data

hazard_class: IRRITANT

Chemistry & industry

Applications · 1 item

Uses5-[(4-Hydroxyphenyl)methylene]-2,4-thiazolidinedione is a 5-Benzylidene-2,4-thiazolidenedione derivative designed as inhibitors of angiogenesis targeting VEGFR-2. Also, it is an intermediate used in the synthesis of MSDC 0602 (M755420), which is an analogue ofthiazolidinediones, exhibits low affinity for binding and activation of peroxisome proliferator-activated receptor γ (PPARγ). Thiazolidinediones are effective insulin-sensitizing drugs for treating various metabolic and inflammatory diseases.