144368-21-8

Basic information

• Product Name: ITACONIC ACID
• Synonyms: PROPYLENEDICARBOXYLIC ACID;2-PROPENE-1,2-DICARBOXYLIC ACID;2-Methylene succinic acid;3-CARBOXY-3-BUTENOIC ACID;ITACONIC ACI
• CAS NO: 144368-21-8
• Molecular Formula: C₆H₈O₄
• Molecular Weight: 130.1
• EINECS: 202-599-6
• Mol File: 144368-21-8.mol

Chemical Properties

• Melting Point: 165-168 °C(lit.)
• Boiling Point: 379.3 °C at 760 mmHg
• Flash Point: 197.3 °C
• Appearance: /
• Density: 1.573 g/mL at 25 °C(lit.)
• CAS DataBase Reference: ITACONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: ITACONIC ACID(144368-21-8)
• EPA Substance Registry System: ITACONIC ACID(144368-21-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 1
• Hazardous Substances Data: 144368-21-8(Hazardous Substances Data)

Upstream product

• 90594-33-5 3-Methyl-1,1,2,2-cyclopropantetracarbonitril 
• 130165-77-4 2-Eth-(E)-ylidene-succinic acid 1-methyl ester 
• 13074-60-7 monoethylmaleic acid 
• 16048-76-3 2-ethyl-3-hydroxy-succinic acid 
• 867-13-0 diethoxyphosphoryl-acetic acid ethyl ester 
• 15933-07-0 Ethyl 2-oxobutanoate 
• 141331-34-2 diethyl 2-ethylidenesuccinate 
• 42162-53-8 (E)-dimethyl 2-ethylidenesuccinate 

Downstream Products

• 4074-24-2 (R)-2-Ethylbutannedioic acid 
• 687-28-5 S-(-)-2-ethylsuccinic acid 
• 129339-83-9 (R)-2-Ethyl-N¹,N⁴-diphenyl-succinamide 
• 129339-91-9 (S)-2-Ethyl-N¹,N⁴-diphenyl-succinamide 
• 636-48-6 monoethylsuccinic acid 
• 1390618-59-3 C₁₂H₁₃ClN₂O₂ 
• 1390618-60-6 C₁₁H₁₃ClN₂O 
• 1390618-58-2 C₁₂H₁₂ClNO₃ 

Relevant articles and documents

NOVEL 4-AMINO-N-HYDROXY-BENZAMIDES FOR THE TREATMENT OF CANCER

The present invention provides compounds of formula or pharmaceutically acceptable salts, esters or stereoisomers thereof, wherein R1 to R4, A and Y have the meanings given herein, as well as methods for making those compounds and their use as medicament, in particular as medicament for the treatment of cancer.

NOVEL 4-AMINO-N-HYDROXY-BENZAMIDES AS HDAC INHIBITORS FOR THE TREATMENT OF CANCER

The present invention provides HDAC inhibitors of formula (I), or pharmaceutically acceptable salts, esters or stereoisomers thereof, wherein R1 to R4, A and Y have the meanings given herein, as well as methods for making those compounds and their use as medicament, in particular as medicament for the treatment of cancer

2-Benzyl-2-methylsuccinic acid as inhibitor for carboxypeptidase A. synthesis and evaluation

Recently, Asante-Appiah et al. (Asante-Appiah, E.; Seetharaman, J.; Sicheri, F.; Yang, D. S.-C.; Chan, W. W.-C. Biochemistry 1997, 36, 8710-8715) reported that 2-ethyl-2-methylsuccinic acid is a highly potent inhibitor for carboxypeptidase A (CPA), a prototypic zinc protease. The X-ray crystal structure of the complex of the enzyme formed with 2-ethyl-2-methylsuccinic acid revealed that at the active site of CPA there is present a small cavity which accommodates the methyl group of the inhibitor. These investigators postulated that incorporation of a methyl group at the α-position to the carboxylate of existing inhibitors of CPA would improve the inhibitory potency. We have synthesized racemic and optically active 2-benzyl-2-methylsuccinic acids and evaluated their inhibitory activities for CPA to find the K(i) values to be 0.28, 0.15, and 17μM for racemic form, (R)-, and (S)-enantiomer, respectively. Contrary to the expectation, the effect on the binding affinity by the incorporation of the methyl group is minimal. The validity of the proposition that the small cavity may be utilized for the improvement of the inhibitory potency appears questionable. Copyright (C) 1999 Elsevier Science Ltd.

Preparation of (S)-2-Substituted Succinates by Stereospecific Reductions of Fumarate and Derivatives with Resting Cells of Clostridium formicoaceticum

Fumarate derivatives have been reduced to (S)-2-methylsuccinate 2a, (S)-2-ethylsuccinate 3a and (S)-2-chlorosuccinate 4a in up to 1 M concentrations with Clostridium formicoaceticum.Formate was the electron donor and viologens or anthraquinone-2,6-disulphonate acted as artificial electron mediators.Reductions with freeze-dried cells in 2H2O-buffers led to the (2R,3S)--dideuterated succinate derivatives.The productivity numbers ranged from 450 to 5000 and the enantiomeric excess of all (S)-2-substituted succinates was >/= 99percent.