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Mucic acid



Mucic acid
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, (also known as galactaric or meso-galactaric acid) is obtained by nitric acid oxidation of galactose or galactose-containing compounds like lactose, dulcite, quercite, and most varieties of gum.

Additional recommended knowledge

It forms a crystalline powder which melts at 213 °C. It is insoluble in alcohol, and nearly insoluble in cold water. Due to the symmetry in the molecule, it is optically inactive even though it has chiral carbon atoms (i.e., it is a meso compound). 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.  

References

  • This article incorporates text from the Encyclopædia Britannica Eleventh Edition, a publication now in the public domain.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Mucic_acid". A list of authors is available in Wikipedia.
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