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301566

Sigma-Aldrich

2,2,3,3-Tetramethylcyclopropanecarboxylic acid

99%

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About This Item

Fórmula lineal:
(CH3)4C3HCO2H
Número de CAS:
15641-58-4
Peso molecular:
142.20
MDL number:
MFCD00011538
UNSPSC Code:
12352100
PubChem Substance ID:
24858197
NACRES:
NA.22

assay

99%

mp

120-121 °C (lit.)

SMILES string

CC1(C)C(C(O)=O)C1(C)C

InChI

1S/C8H14O2/c1-7(2)5(6(9)10)8(7,3)4/h5H,1-4H3,(H,9,10)

InChI key

SFHVXKNMCGSLAR-UHFFFAOYSA-N

General description

2,2,3,3-Tetramethylcyclopropanecarboxylic acid is an inactive cyclopropyl analog of valproic acid (major antiepileptic drug). Inhibition of histone deacetylases and tumor cells cytotoxicities of 2,2,3,3-tetramethylcyclopropanecarboxylic acid was studied.

Application

2,2,3,3-Tetramethylcyclopropanecarboxylic acid was used as a starting material for the synthesis of central nervous system-active compounds.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Preparation of tetramethylcyclopropanecarboxylic-14C acid and insecticidal terallethrin-14C from it.
A Yoshitake et al.
Radioisotopes, 30(8), 452-454 (1981-08-01)
Sara Eyal et al.
Biochemical pharmacology, 69(10), 1501-1508 (2005-04-29)
The tumor cells toxicity of the antiepileptic drug valproic acid (VPA) has been associated with the inhibition of histone deacetylases (HDACs). We have assessed, in comparison to VPA, the HDACs inhibition and tumor cells cytotoxicities of CNS-active VPA's constitutional isomers
Neta Pessah et al.
Journal of medicinal chemistry, 52(8), 2233-2242 (2009-03-20)
2,2,3,3-Tetramethylcyclopropanecarboxylic acid (TMCA, 4) is a cyclic analogue of the antiepileptic drug (AED) valproic acid (VPA) (1). alpha-F, alpha-Cl, alpha-Br, and alpha-methyl derivatives of 4 and their amides were synthesized and tested in rodent models for anticonvulsant potency and AED-induced
Tawfeeq Shekh-Ahmad et al.
Epilepsy research, 98(2-3), 238-246 (2011-11-08)
Valproic acid (VPA) is a major antiepileptic drug (AED) that is less potent than other AEDs. 2,2,3,3-Tetramethylcyclopropanecarboxylic acid (TMCA) is an inactive cyclopropyl analogue of VPA that serves as a starting material for the synthesis of CNS-active compounds. New conjugation

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