Butanedioic acid

Butanedioic acid
Compound Structure:
Synonyms: succinic acid;butanedioic acid;110-15-6;Amber acid;Asuccin;Wormwood acid;Dihydrofumaric acid;Katasuccin;Bernsteinsaure;1,2-Ethanedicarboxylic acid;ethylenesuccinic acid;1,4-Butanedioic acid;Wormwood;Succinicum acidum;Butandisaeure
Compound ID: NMPC-692
PubChem ID:

1110

Molecular Formula: C4H6O4
Canonical SMILES: C(CC(=O)O)C(=O)O
InChIKey: KDYFGRWQOYBRFD-UHFFFAOYSA-N
About the compound:

Succinic acid, also known by its IUPAC name as butanedioic acid, is an alpha,omega-dicarboxylic acid. It is formed through the formal oxidation of each of the terminal methyl groups in butane to carboxyl groups. Chemically, it is characterized as an intermediate metabolite in the citric acid cycle, a crucial pathway in cellular respiration. In addition to its role in metabolism, succinic acid has various applications and functions. It is used as a nutraceutical, a radiation protective agent, an anti-ulcer drug, and a micronutrient. Moreover, it is considered a fundamental metabolite in biological systems. Structurally, it is both an alpha,omega-dicarboxylic acid and a C4-dicarboxylic acid, and it forms a conjugate acid of a succinate(1-). Succinic acid appears as water-soluble, colorless crystals with an acidic taste. It serves as a chemical intermediate in various industrial processes, including in the manufacture of lacquers and perfume esters. In the realm of food production, it is used as a sequestrant, buffer, and neutralizing agent. Its applications are recognized in numerous references, including Hawley's Condensed Chemical Dictionary and the McGraw-Hill Dictionary of Scientific and Technical Terms. Biologically, succinic acid is important as it forms an anion called succinate in living organisms. Succinate plays a vital role as a metabolic intermediate, being converted into fumarate by succinate dehydrogenase in the electron transport chain. This process is essential in ATP (adenosine triphosphate) production. Succinate also functions as a signaling molecule, reflecting the metabolic state of a cell. Succinate is produced in the mitochondria via the tricarboxylic acid cycle (TCA) and can impact functions both within the cytoplasm and the extracellular space. It influences gene expression patterns, modulates the epigenetic landscape, and exhibits hormone-like signaling, thus linking cellular metabolism to the regulation of cellular functions. Dysregulation of succinate synthesis, and consequently ATP synthesis, is observed in some genetic mitochondrial diseases, such as Leigh syndrome and Melas syndrome. Imbalances in succinate levels can lead to various pathological conditions, including malignant transformation, inflammation, and tissue injury. In the food industry, succinic acid is marketed as the food additive E363. The name 'succinic' originates from the Latin word "succinum," meaning amber, reflecting its historical association.

GHS Hazard Statements

H318 (84.8%): Causes serious eye damage [Danger Serious eye damage/eye irritation]

H319 (13.93%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

First Aid

For eye exposure, remove contact lenses, flush with water for 20-30 minutes, and seek medical help.

For skin exposure, flood with water, wash with soap, and seek medical help if symptoms arise.

If inhaled, move to fresh air, seek medical help for symptoms, provide respiratory protection.

For ingestion, do not induce vomiting, give water if conscious, seek medical advice, and ensure airway if unconscious (NTP, 1992).

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

118.09 g/mol

XLogP3

-0.6

Hydrogen Bond Donor Count

2

Hydrogen Bond Acceptor Count

4

Rotatable Bond Count

3

Exact Mass

118.02660867 g/mol

Monoisotopic Mass

118.02660867 g/mol

Topological Polar Surface Area

74.6Ų

Heavy Atom Count

8

Formal Charge

0

Complexity

92.6

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Physical Description

Colourless or white, odourless crystals

Boiling Point

235 °C

Melting Point

188°C

Density

1.572 at 68 °F (NTP, 1992) - Denser than water; will sink

Solubility 

Soluble in ethanol, ethyl ether, acetone, methanol; slightly soluble in deuterated dimethyl formamide; insoluble in toluene, benzene.

Vapor Pressure

0.00000019 [mmHg]

Source: PubChem

Source Species: Petiveria alliacea
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