Mucic acid

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Mucic acid
Mucic acid structure.png
Identifiers
CAS number 526-99-8 YesY
PubChem 3037582
ChemSpider 2301286 N
ChEMBL CHEMBL1232958 N
Jmol-3D images Image 1
Properties
Molecular formula C6H10O8
Molar mass 210.14 g mol−1
Melting point 230 °C (446 °F; 503 K)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Mucic acid, C6H10O8 or HOOC-(CHOH)4-COOH, (also known as galactaric or meso-galactaric acid) is an aldaric acid obtained by nitric acid oxidation of galactose or galactose-containing compounds such as lactose, dulcite, quercite, and most varieties of gum.

Properties[edit]

Mucic acid forms a crystalline powder, which melts at 230 °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).

Reactions[edit]

When heated with pyridine to 140 °C, it is converted into allomucic acid.[1] 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.

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

Use[edit]

Mucic acid can be used to replace tartaric acid in self-rising flour or fizzies.

It has been used as a precursor of adipic acid en route to nylon by a rhenium-catalyzed deoxydehydration reaction.[2]

References[edit]

  1. ^ Butler, C. L.; Cretcher, L. H. (1929). "The Preparation of Allomucic Acid and Certain of Its Derivatives". Journal of the American Chemical Society 51 (7): 2167. doi:10.1021/ja01382a029.  edit
  2. ^ Li, X.; Wu, D.; Lu, T.; Yi, G.; Su, H.; Zhang, Y. (2014). "Highly Efficient Chemical Process to Convert Mucic Acid into Adipic Acid and DFT Studies of the Mechanism of the Rhenium-Catalyzed Deoxydehydration". Angewandte Chemie International Edition 53 (16): 4200. doi:10.1002/anie.201310991.  edit