301566
2,2,3,3-Tetramethylcyclopropanecarboxylic acid
99%
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Linear Formula:
(CH3)4C3HCO2H
CAS Number:
Molecular Weight:
142.20
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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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.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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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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