692-29-5

Basic information

• Product Name: SUCCINALDEHYDIC ACID
• Synonyms: SUCCINALDEHYDIC ACID;SUCCINIC SEMIALDEHYDE;BETA-FORMYLPROPIONIC ACID;4-OXO-BUTANOIC ACID;4-OXOBUTYRIC ACID;3-formylpropanoicacid;3-formylpropionicacid;4-oxo-butanoicaci
• CAS NO: 692-29-5
• Molecular Formula: C₄H₆O₃
• Molecular Weight: 102.09
• Product Categories: Aldehydes;Building Blocks;C1 to C6;Carbonyl Compounds;Chemical Synthesis;Organic Building Blocks
• Mol File: 692-29-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 202-203 °C(Solv: methanol (67-56-1))
• Boiling Point: 248.6 °C at 760 mmHg
• Flash Point: 118.4 °C
• Appearance: /
• Density: 1.09 g/mL at 25 °C
• Vapor Pressure: 0.00768mmHg at 25°C
• Refractive Index: 1.429
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.69±0.17(Predicted)
• CAS DataBase Reference: SUCCINALDEHYDIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: SUCCINALDEHYDIC ACID(692-29-5)
• EPA Substance Registry System: SUCCINALDEHYDIC ACID(692-29-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26
• Hazardous Substances Data: 692-29-5(Hazardous Substances Data)

Usage

Description

SUCCINALDEHYDIC ACID, also known as β-Formylpropionic Acid, is an organic compound that serves as a key intermediate in the synthesis of various pharmaceutical compounds. It possesses a unique chemical structure that allows it to be a versatile building block in the development of new drugs.

Uses

Used in Pharmaceutical Industry:
SUCCINALDEHYDIC ACID is used as a key intermediate for the synthesis of potent and orally available nonpeptide antagonists of the human gonadotropin-releasing hormone receptor. This application is significant because it helps in the development of treatments for conditions related to the hormonal regulation, such as infertility and certain types of cancer.
Additionally, SUCCINALDEHYDIC ACID is used as a reagent in the synthesis of human melanocortin-4 receptor antagonists with a pyrrolidinone moiety. These antagonists have potential applications in the treatment of obesity and related metabolic disorders by modulating the melanocortin system, which is involved in the regulation of energy balance and food intake.

Synthesis Reference(s)

Tetrahedron Letters, 14, p. 3535, 1973 DOI: 10.1016/S0040-4039(01)86963-X

InChI:InChI=1/C4H6O3/c5-3-1-2-4(6)7/h3H,1-2H2,(H,6,7)

Upstream product

• 617-65-2 Glutamic acid 
• 79-15-2 N-bromoacetamide 
• 1821-34-7 N-chlorobenzamide 
• 52316-62-8 N-chloro-L-glutamic acid 
• 98-01-1 furfural 
• 543-20-4 succinoyl dichloride 
• 328-50-7 α-ketoglutaric acid 
• 7732-18-5 water 
• 56-12-2 4-amino-n-butyric acid 
• 56-86-0 L-glutamic acid 
• 110-83-8 cyclohexene 
• 591-81-1 4-hydroxybutanoic acid 
• 108-31-6 maleic anhydride 

Downstream Products

• 10138-10-0 ethyl 4-oxobutanoate 
• 110-15-6 succinic acid 
• 1912-47-6 2-(5-methyl-1H-indol-3-yl)acetic acid 
• 100128-31-2 4-[methyl-(4-nitro-phenyl)-hydrazono]-butyric acid 
• 13865-19-5 4-oxobutanoic acid methyl ester 
• 932-85-4 γ-ethoxy-γ-butyrolactone 
• 4220-65-9 ethyl 4,4-diethoxybutanoate 
• 195299-15-1 2-cyano-5-oxazolopyrrolidine 
• 111998-68-6 (R)-2-Phenyl-2-pyrrol-1-yl-ethanol 
• 111998-65-3 (2R,5S)-1-((R)-2-Hydroxy-1-phenyl-ethyl)-pyrrolidine-2,5-dicarbonitrile 
• 116127-24-3 (2R,5R)-1-((R)-2-Hydroxy-1-phenyl-ethyl)-pyrrolidine-2,5-dicarbonitrile 
• 4093-65-6 succinic semialdehyde 2,4-dinitrophenylhydrazone 
• 73786-17-1 C₁₆H₁₄S₄ 

Relevant articles and documents

Rearrangements and Tautomeric Transformations of Heterocyclic Compounds in Homogeneous Reaction Systems Furfural–Н2О2–Solvent

General information on the reactions of furfurals with hydrogen peroxide is given. We have discussed the Baeyer–Villiger rearrangement of furan 2-hydroxyhydroperoxides and tautomeric transformations with proton transfer of 2-hydroxyfuran and β-formylacrylic acid formed in a homogeneous reaction system furfural–Н2О2–solvent under the catalysis with the formed acids. The factors affecting these rearrangements and tautomeric transformations as well as their specificity in comparison with benzene type compounds, and the pathway of the reactions of furan aldehydes with Н2О2 in water have been analyzed. Ketoenol tautomerism of cyclic hemiacetal form of β-formylacrylic acid leading to its transformation into succinic anhydride has been described for the first time.

Inhibition of 1,4-butanediol metabolism in human liver in vitro

The conversion of 1,4-butanediol (1,4-BD) to gamma-hydroxybutyric acid (GHB), a drug of abuse, is most probably catalyzed by alcohol dehydrogenase, and potentially by aldehyde dehydrogenase. The purpose of this study was to investigate the degradation of 1,4-BD in cytosolic supernatant of human liver in vitro, and to verify involvement of the suggested enzymes by means of gas chromatography-mass spectrometry. The coingestion of 1,4-BD and ethanol (EtOH) might cause complex pharmacokinetic interactions in humans. Therefore, the effect of EtOH on 1,4-BD metabolism by human liver was examined in vitro. Additionally, the influence of acetaldehyde (AL), which might inhibit the second step of 1,4-BD degradation, was investigated. In case of a 1,4-BD intoxication, the alcohol dehydrogenase inhibitor fomepizole (4-methylpyrazole, FOM) has been discussed as an antidote preventing the formation of the central nervous system depressing GHB. Besides FOM, we tested pyrazole, disulfiram, and cimetidine as possible inhibitors of the formation of GHB from 1,4-BD catalyzed by human liver enzymes in vitro. The conversion of 1,4-BD to GHB was inhibited competitively by EtOH with an apparent K i of 0.56 mM. Therefore, the coingestion of 1,4-BD and EtOH might increase the concentrations and the effects of 1,4-BD itself. By contrast AL accelerated the formation of GHB. All antidotes showed the ability to inhibit the formation of GHB. In comparison FOM showed the highest inhibitory effectiveness. Furthermore, the results confirm strong involvement of ADH in 1,4-BD metabolism by human liver.

Aerosol formation in the cyclohexene-ozone system

Atmospheric oxidation of certain VOCs can yield products with low vapor pressure resulting in the partitioning of the products into the aerosol phase, producing secondary organic aerosol. As cyclohexene is known to produce aerosol upon photooxidation, it was used as a model system for the molecular identification of gas- and aerosol-phase products via derivatization and MS detection. Adipic acid, hydroxyglutaric acid, and hydroxyadipic acid were among the compounds identified in the aerosol phase. Pentanal was the predominant product in the gas phase at a molar yield of 17%. Possible explanations for the presence of relatively high vapor pressure compounds in the aerosol phase are presented.