Mucic acid

Names
IUPAC name

(2S,3R,4S,5R)-2,3,4,5-Tetrahydroxyhexanedioic acid

Other names

Galactaric acid; Galactosaccharic acid

Identifiers

CAS Number

* 526-99-8 Y

3D model (JSmol)

* Interactive image

ChEMBL |

* ChEMBL1232958 N

ChemSpider |

* 2301286 N

PubChem CID

* 3037582

UNII |

* E149J5OTIF Y

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- N

Key: DSLZVSRJTYRBFB-DUHBMQHGSA-N 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@@H]([C@@H]([C@H](C(=O)O)O)O)([C@@H](C(=O)O)O)O

Properties

Chemical formula

| C6H10O8
Molar mass | 210.138 g·mol−1
Melting point |  230 °C (446 °F; 503 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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.[1]

## Contents

* 1 Properties
* 2 Reactions
* 3 Use
* 4 See also
* 5 References

## Properties

Mucic acid forms a crystalline powder, which melts at 210–230 °C.[2] It is insoluble in alcohol, and nearly insoluble in cold water.[1] 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.[1][3] 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.[1] The ammonium salt yields on dry distillation carbon dioxide, ammonia, pyrrol and other substances.[1] The acid when fused with caustic alkalis yields oxalic acid.[1]

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.[4]

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

## See also

* Muconic acid

## References

1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 Chisholm, Hugh, ed (1911). "Mucic Acid". Encyclopædia Britannica. 18 (11th ed.). Cambridge University Press. p. 954.
2. ↑ "Mucic acid". ChemSpider. http://www.chemspider.com/Chemical-Structure.2301286.html. 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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*[CID]: Compound ID