コハク酸、コハク酸塩、コハク酸エステル, succinic acid
出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2013/09/04 12:33:50」(JST)
Succinic acid | |
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IUPAC name
Butanedioic acid |
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Other names
ethane-1,2-dicarboxylic acid |
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Identifiers | |
CAS number | 110-15-6 Y |
PubChem | 1110 |
ChemSpider | 1078 Y |
UNII | AB6MNQ6J6L Y |
DrugBank | DB00139 |
ChEBI | CHEBI:15741 Y |
ChEMBL | CHEMBL576 Y |
Jmol-3D images | Image 1 |
SMILES
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InChI
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Properties | |
Molecular formula | C4H6O4 |
Molar mass | 118.09 g mol−1 |
Density | 1.56 g/cm3[1] |
Melting point |
184 °C, 457 K, 363 °F ([1]) |
Boiling point |
235 °C, 508 K, 455 °F ([1]) |
Solubility in water | 58 g/L (20 °C)[1] |
Acidity (pKa) | pKa1 = 4.2 pKa2 = 5.6 |
Hazards | |
Flash point | 206 °C (403 °F)[1] |
Related compounds | |
Other anions | sodium succinate |
Related carboxylic acids | propionic acid malonic acid |
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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Infobox references |
Succinic acid (/səkˈsɪnɨk/; IUPAC systematic name: butanedioic acid; historically known as spirit of amber) is a diprotic, dicarboxylic acid with chemical formula C4H6O4 and structural formula HOOC-(CH2)2-COOH. It is a white, odorless solid. Succinate plays a role in the citric acid cycle, an energy-yielding process. The name derives from Latin succinum, meaning amber, from which the acid may be obtained.
Spirit of amber was originally obtained from amber by pulverising and distilling it using a sand bath. In the past it was chiefly used externally for rheumatic aches and pains, and internally in inveterate gleets.
Succinic acid is produced by several methods. Common industrial routes include hydrogenation of maleic acid, oxidation of 1,4-butanediol, and carbonylation of ethylene glycol.[2]
Succinic acid can be converted into fumaric acid by oxidation. The diethyl ester is a substrate in the Stobbe condensation. Dehydration of succinic acid gives succinic anhydride.[3]
Succinic acid is a precursor to some specialized polyesters. It is also a component of some alkyd resins.
Succinic acid is used in the food and beverage industry, primarily as an acidity regulator.[4] Global production is estimated at 16,000 to 30,000 tonnes a year, with an annual growth rate of 10%.[5]
In nutraceutical form as a food additive and dietary supplement, is safe and approved by the U.S. Food and Drug Administration.[6] As an excipient in pharmaceutical products it is used to control acidity[7] and, more rarely, in effervescent tablets.[8]
Succinate is an intermediate in the citric acid cycle and is capable of donating electrons to the electron transport chain by the reaction:
Click on genes, proteins and metabolites below to link to respective articles. [§ 1]
This conversion is catalysed by the enzyme succinate dehydrogenase (or complex II of the mitochondrial ETC). The complex is a 4 subunit membrane-bound lipoprotein which couples the oxidation of succinate to the reduction of ubiquinone. Intermediate electron carriers are FAD and three 2Fe-2S clusters part of subunit B.
Succinic acid is created as a byproduct of the fermentation of sugar. It lends to fermented beverages such as wine and beer a common taste that is a combination of saltiness, bitterness and acidity.[9]
Salts formed by neutralizing succinic acid are called succinates. One example is sodium succinate, a white, water-soluble salt. Esters of succinic acid are also called succinates, one example being dimethylsuccinate with the formula (CH2CO2CH3)2.
Succinic acid is an important biochemical intermediate that occurs in all living creatures. Like other simple mono- and dicarboxylic acids, it is not considered dangerous, although it is a skin irritant.[10]
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Oxaloacetate | Malate | Fumarate | Succinate | Succinyl-CoA | ||||||||||||||||||
Acetyl-CoA | NADH + H+ | NAD+ | H2O | FADH2 | FAD | CoA + ATP(GTP) | Pi + ADP(GDP) | |||||||||||||||
+ | H2O | NADH + H+ + CO2 | ||||||||||||||||||||
CoA | NAD+ | |||||||||||||||||||||
H2O | H2O | NAD(P)+ | NAD(P)H + H+ | CO2 | ||||||||||||||||||
Citrate | cis-Aconitate | Isocitrate | Oxalosuccinate | α-Ketoglutarate | ||||||||||||||||||
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リンク元 | 「コハク酸」「スクシニルCoA」「スクシニル」「コハク酸塩」「コハク酸エステル」 |
拡張検索 | 「methylprednisolone hemisuccinate」「succinate-semialdehyde dehydrogenase」「argininosuccinate synthase」「calcium tocopherol succinate」 |
HOOC-CH2-CH2-COOH
HOOC-CH2-CO-S-CoA
-OOC-CH2-CH2-COO-
コハク酸セミアルデヒド脱水素酵素、コハク酸セミアルデヒドデヒドロゲナーゼ
.