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301566

2,2,3,3-Tetramethylcyclopropanecarboxylic acid

Name: 2,2,3,3-Tetramethylcyclopropanecarboxylic acid
Brand: ALDRICH

99%

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About This Item

Linear Formula:

(CH₃)₄C₃HCO₂H

CAS Number:

15641-58-4

Molecular Weight:

142.20

NACRES:

NA.22

PubChem Substance ID:

24858197

UNSPSC Code:

12352100

MDL number:

MFCD00011538

Assay:

99%

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Properties

assay

99%

mp

120-121 °C (lit.)

functional group

carboxylic acid

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

Description

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

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

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)

Alpha-fluoro-2,2,3,3-tetramethylcyclopropanecarboxamide, a novel potent anticonvulsant derivative of a cyclic analogue of valproic acid.

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

Histone deacetylases inhibition and tumor cells cytotoxicity by CNS-active VPA constitutional isomers and derivatives.

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

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Global Trade Item Number

SKU	GTIN
301566-5G	04061831810455
301566-1G	04061825584379