Mucic acid

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Mucic acid
Image:Mucic acid structure.png
IUPAC name (2S,3R,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid
Identifiers
CAS number 526-99-8
PubChem 3037582
SMILES C(C(C(C(=O)O)O)O)(C(C(=O)O)O)O
Properties
Molecular formula C6H10O8
Molar mass 210.1388
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Mucic acid, C6H10O8 or HOOC-(CHOH)4-COOH, is obtained by the oxidation of lactose, dulcite, galactose, quercite and most varieties of gum by nitric acid.

It forms a crystalline powder which melts at 213 °C. It is insoluble in alcohol, and nearly insoluble in cold water. When heated with pyridine to 140 °C, it is converted into allommic acid. When digested with fuming hydrochloric acid for some time it is converted into a furfural dicarboxylic acid while on heating with barium sulfide it is transformed into athiophene carboxylic acid. The ammonium salt yields on dry distillation carbon dioxide, ammonia, pyrrol and other substances. The acid when fused with caustic alkalis yields oxalic acid.

With potassium bisulfate mucic acid forms 3-hydroxy-2-pyrone by dehydration and decarboxylation.

Image:3-hydroxy-2-pyrone.gif
Reaction of mucic acid to 3-hydroxy-2-pyrone with a) potassium bisulfate 160 °C / 4 hrs. b) hydrochloric acid to pH = 7

References


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Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .

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