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Mucic acid

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(Redirected from Ammonium mucate)
Mucic acid
Structural formula of mucic acid
Ball-and-stick model of the mucic acid molecule
Names
IUPAC name (2S,3R,4S,5R)-2,3,4,5-Tetrahydroxyhexanedioic acid
Other names Galactaric acid; Galactosaccharic acid
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.007.641 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2+,3+,4-Key: DSLZVSRJTYRBFB-DUHBMQHGSA-N
  • InChI=1/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2+,3+,4-Key: DSLZVSRJTYRBFB-DUHBMQHGBT
SMILES
  • (((C(=O)O)O)O)((C(=O)O)O)O
Properties
Chemical formula C6H10O8
Molar mass 210.138 g·mol
Melting point 230 °C (446 °F; 503 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Mucic acid, C6H10O8 or HOOC-(CHOH)4-COOH (galactaric acid 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

Mucic acid forms a crystalline powder, which melts at 210–230 °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

When heated with pyridine to 140 °C, it is converted into allomucic acid. When digested with fuming hydrochloric acid for some time it is converted into αα′ furfural dicarboxylic acid while on heating with barium sulfide it is transformed into α-thiophene 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

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

It has been used as a precursor of adipic acid in the way to nylon by a rhenium-catalyzed deoxydehydration reaction.

It has been used as a precursor of Taxol in Nicolaou Taxol total synthesis (1994).

See also

References

  1. ^ Chisholm, Hugh, ed. (1911). "Mucic Acid" . Encyclopædia Britannica. Vol. 18 (11th ed.). Cambridge University Press. p. 954.
  2. "Mucic acid". ChemSpider. Retrieved 30 March 2018.
  3. 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.
  4. 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): 4200–4204. doi:10.1002/anie.201310991. PMID 24623498.
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