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{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 397956868
| Watchedfields = changed
⚫ |ImageFile=mucic acid structure.png
⚫ | verifiedrevid = 440609265
⚫ |ImageSize=200px
⚫ | ImageFile=mucic acid structure.png
⚫ |IUPACName=(2''S'',3''R'',4''S'',5''R'')-2,3,4,5-tetrahydroxyhexanedioic acid
⚫ | ImageSize=200px
⚫ |OtherNames=Galactaric acid
| ImageAlt = Structural formula of mucic acid
⚫ |Section1= {{Chembox Identifiers
| ImageFile1 = Mucic acid molecule ball.png
⚫ | CASNo=526-99-8
| ImageAlt1 = Ball-and-stick model of the mucic acid molecule
⚫ | PubChem=3037582
⚫ | IUPACName=(2''S'',3''R'',4''S'',5''R'')-2,3,4,5-Tetrahydroxyhexanedioic acid
⚫ | SMILES=C(C(C(C(=O)O)O)O)(C(C(=O)O)O)O
⚫ | OtherNames=Galactaric acid; Galactosaccharic acid
⚫ |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
⚫ | CASNo=526-99-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = E149J5OTIF
⚫ | PubChem=3037582
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1232958

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 2301286
⚫ | SMILES = (((C(=O)O)O)O)((C(=O)O)O)O
| 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-
| InChIKey = DSLZVSRJTYRBFB-DUHBMQHGBT
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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-
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = DSLZVSRJTYRBFB-DUHBMQHGSA-N
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=6 | H=10 | O=8
| Formula=C<sub>6</sub>H<sub>10</sub>O<sub>8</sub>
| Appearance=
| MolarMass=210.1388
| Appearance= | Density=
| MeltingPtC=230
| Density=
| MeltingPt= | BoilingPt=
| BoilingPt= | Solubility=
| Solubility=
}} }}
|Section3= {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards= | MainHazards=
| FlashPt= | FlashPt=
| AutoignitionPt =
| Autoignition=
}} }}
}} }}


'''Mucic acid''', C<sub>6</sub>H<sub>10</sub>O<sub>8</sub> or HOOC-(CHOH)<sub>4</sub>-COOH, (also known as galactaric or meso-galactaric acid) is obtained by ] oxidation of ] or galactose-containing compounds like ], ], ], and most varieties of ]. '''Mucic acid''', C<sub>6</sub>H<sub>10</sub>O<sub>8</sub> or HOOC-(CHOH)<sub>4</sub>-COOH ('''galactaric acid''' or '''meso-galactaric acid''') is an ] obtained by ] oxidation of ] or galactose-containing compounds such as ], ], ], and most varieties of ].<ref name=EB1911>{{cite EB1911 |wstitle=Mucic Acid |volume=18 |page=954}}</ref>


==Properties==
⚫ It forms a crystalline powder which melts at 213 °C. It is insoluble in ], and nearly insoluble in cold water. Due to the symmetry in the molecule, it is ] even though it has ] carbon atoms (i.e., it is a ]). When heated with ] to 140 °C, it is converted into ]. When digested with fuming ] for some time it is converted into a ] ] while on heating with ] ] it is transformed into ] carboxylic acid. The ] yields on dry distillation ], ], ] and other substances. The acid when fused with caustic alkalis yields ].
Mucic acid forms a crystalline powder, which melts at 210–230&nbsp;°C.<ref>{{cite web |url=http://www.chemspider.com/Chemical-Structure.2301286.html |title=Mucic acid |work=ChemSpider |accessdate=30 March 2018}}</ref> It is insoluble in ], and nearly insoluble in cold water.<ref name=EB1911/> Due to the symmetry in the molecule, it is ] even though it has ] carbon atoms (i.e., it is a ]).

==Reactions==
⚫ When heated with ] to 140&nbsp;°C, it is converted into ].<ref name=EB1911/><ref>{{Cite journal | doi = 10.1021/ja01382a029| title = The Preparation of Allomucic Acid and Certain of Its Derivatives| journal = Journal of the American Chemical Society| volume = 51| issue = 7| pages = 2167| year = 1929| last1 = Butler | first1 = C. L.| last2 = Cretcher | first2 = L. H. }}</ref> When digested with fuming ] for some time it is converted into αα′ ] ] while on heating with ] ] it is transformed into α-] carboxylic acid.<ref name=EB1911/> The ] yields on dry distillation ], ], ] and other substances.<ref name=EB1911/> The acid when fused with caustic alkalis yields ].<ref name=EB1911/>

⚫ With ] mucic acid forms 3-hydroxy-2-pyrone by dehydration and decarboxylation.
⚫ :] 160&nbsp;°C / 4 hrs. b) ] to ] = 7]]{{clear|left}}


⚫ With ] mucic acid forms '''3-hydroxy-2-pyrone''' by dehydration and decarboxylation.
⚫ ] 160 ] / 4 hrs. b) ] to ] = 7]]<br style="clear:left;"/>
==Use== ==Use==
Mucic acid can be used to replace ] in self rising flour or ]. Mucic acid can be used to replace ] in ] or ].

It has been used as a precursor of ] in the way to ] by a rhenium-catalyzed ] reaction.<ref>{{Cite journal | doi = 10.1002/anie.201310991| title = Highly Efficient Chemical Process to Convert Mucic Acid into Adipic Acid and DFT Studies of the Mechanism of the Rhenium-Catalyzed Deoxydehydration| journal = Angewandte Chemie International Edition| volume = 53| issue = 16| pages = 4200–4204| year = 2014| last1 = Li | first1 = X. | last2 = Wu | first2 = D. | last3 = Lu | first3 = T. | last4 = Yi | first4 = G. | last5 = Su | first5 = H. | last6 = Zhang | first6 = Y. | pmid=24623498}}</ref>

It has been used as a precursor of ] in ] (1994).

==See also==
* ]

==References== ==References==
*{{1911}} {{reflist}}


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] ]

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