4198-33-8

Basic information

• Product Name: (S)-2-CHLOROSUCCINIC ACID
• Synonyms: BUTANEDIOIC ACID, CHLORO-, (2S)-;(S)-(-)-2-CHLOROSUCCINIC ACID;(S)-2-CHLOROSUCCINIC ACID;L-2-chlorosuccinic acid crystalline;(S)-chlorosuccinic acid;(S)-2-CHLOROSUCCINIC ACID ,99%MIN;(S)-2-Chlorobutanedioic acid;L-Chlorosuccinic acid
• CAS NO: 4198-33-8
• Molecular Formula: C₄H₅ClO₄
• Molecular Weight: 152.53
• EINECS: 224-092-9
• Mol File: 4198-33-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: 150-153 °C
• Boiling Point: 235.8 °C at 760 mmHg
• Flash Point: 96.4 °C
• Appearance: /
• Density: 1.595 g/cm³
• Vapor Pressure: 0.017mmHg at 25°C
• Refractive Index: 1.509
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-2-CHLOROSUCCINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-CHLOROSUCCINIC ACID(4198-33-8)
• EPA Substance Registry System: (S)-2-CHLOROSUCCINIC ACID(4198-33-8)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261
• Hazardous Substances Data: 4198-33-8(Hazardous Substances Data)

Usage

General Description

(S)-2-Chlorosuccinic acid is a chemical compound with the molecular formula C4H4Cl2O4. It is a derivative of succinic acid, a dicarboxylic acid found in the body as an intermediate in the citric acid cycle. (S)-2-Chlorosuccinic acid is a chiral compound, meaning it has non-superimposable mirror images, or enantiomers. (S)-2-CHLOROSUCCINIC ACID has been studied for its potential use in the synthesis of various pharmaceuticals and as a building block in organic chemistry. It is also used in research as a chiral resolving agent and in the development of new catalytic processes. Additionally, it has potential applications in the fields of agriculture and material science.

InChI:InChI=1/C4H5ClO4/c5-2(4(8)9)1-3(6)7/h2H,1H2,(H,6,7)(H,8,9)/t2-/m0/s1

Upstream product

• 56-84-8 L-Aspartic acid 
• 617-42-5 chlorofumaric acid 
• 617-45-8 aspartic Acid 
• 7647-01-0 hydrogenchloride 

Downstream Products

• 3972-40-5 (2R)-chlorobutanedioic acid 
• 111618-88-3 dimethyl (2R)-chlorobutanedioate 
• 541-15-1 L-carnitine 

Relevant articles and documents

Identification and pharmacological characterization of succinate receptor agonists

Background and Purpose: The succinate receptor (formerly GPR91 or SUCNR1) is described as a metabolic sensor that may be involved in homeostasis. Notwithstanding its implication in important (patho)physiological processes, the function of succinate receptors has remained ill-defined because no pharmacological tools were available. We report on the discovery of the first family of potent synthetic agonists. Experimental Approach: We screened a library of succinate analogues and analysed their activity on succinate receptors. Also, we modelled a pharmacophore and a binding site for this receptor. New agonists were identified based on the information provided by these two approaches. Their activity was studied in various bioassays, including measurement of cAMP levels, [Ca2+]i mobilization, TGF-α shedding and recruitment of arrestin 3. The in vivo effects of activating succinate receptors with these new agonists was evaluated on rat BP. Key Results: We identified cis-epoxysuccinic acid and cis-1,2-cyclopropanedicarboxylic acid as agonists with an efficacy similar to that of succinic acid. Interestingly, cis-epoxysuccinic acid was 10- to 20-fold more potent than succinic acid on succinate receptors. For example, cis-epoxysuccinic acid reduced cAMP levels with a pEC50?=?5.57?±?0.02 (EC50?=?2.7?μM), compared with succinate pEC50?=?4.54?±?0.08 (EC50?=?29?μM). The rank order of potency of the three agonists was the same in all in vitro assays. Both cis-epoxysuccinic and cis-1,2-cyclopropanedicarboxylic acid were as potent as succinate in increasing rat BP. Conclusions and Implications: We describe new agonists at succinate receptors that should facilitate further research on this understudied receptor.

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.

Application of (2)H N.M.R. Spectroscopy to Study the Incorporation of Enantiomeric -Labelled Putrescines into the Pyrrolizidine Alkaloid Retrorsine

A sample of (2R)-putrescine (13) dihydrochloride was prepared from (2S)-aspartic acid (8), and (2S)-putrescine (15) dihydrochloride was synthesized from (2R)-aspartic acid.Feeding experiments carried out with these precursors on Senecio isatideus plants gave retrorsine (5) containing (2)H, and the distribution of (2)H from each experiment in retrorsine was determined by (2)H n.m.r. spectroscopy.All of the (2)H was confined to the base component of the alkaloid, retronecine (4).Retrorsine (14), derived biosynthetically from (2R)-putrescine (13) dihydrochloride was labelled with (2)H at C-2 and C-6α, while retrorsine (16), produced from (2S)-putrescine (15) dihydrochloride contained (2)H labels at C-6β and C-7α.These labelling patterns demonstrate that hydroxylation at C-7 of retronecine (4) proceeds with retention of configuration.In addition, the formation of the 1,2-double bond of retronecine involves removal of the pro-S hydrogen and retention of the pro-R hydrogen at the carbon atom which becomes C-2 of retronecine.