Synthesis of mucic acid

Preparation of mucic acid

Alternative Names: Schleimsaure; Tetrahydroxyadipic acid; Saccharolactic acid; Galactaric acid, D-; 2,3,4,5-Tetrahydroxyhexanedioic acid;

Preparation of mucic acid

Preparation of mucic acid

100 g lactose are evaporated in a porcelain dish with 1200 g nitric acid (sp. gr. 1.15) to a volume of about 200 ml, the mixture being kept stirred towards the end. The mass becomes thick and pasty owing to separation of mucic acid. When cold it is diluted with water, filtered, and washed with cold water. In order to determine the yield of raw product, which should amount to about 36 g dry substance, the wet mass is weighed and an aliquot part of it (about 1 g.) is dried at 100° C.  To purify it completely, the mucic acid is dissolved in sodium hydroxide solution, and precipitated again with acid. It must be noticed, however, that only the neutral sodium salt, is easily soluble in water, and, moreover, its solubility also is decreased by excess of alkali. It is therefore best to calculate approximately the amount of sodium hydroxide and to add that quantity in the form of normal sodium hydroxide solution. For the above amount of raw product about 335 ml of normal alkali are required. The mucic acid dissolves in this liquid on shaking without the application of heat. If the solution is yellow it is decolorized by warming with activated charcoal. If already colorless, it is treated at once with enough hydrochloric acid to combine with all the sodium. For this purpose about 67 ml of five times normal hydrochloric acid are necessary. The addition of the acid must not take place in the warm, but at ordinary temperature; otherwise part of the mucic acid is converted into the easily soluble lactone. The mucic acid soon crystallizes out after the addition of the hydrochloric acid. To complete the crystallization the liquid is allowed to stand for an hour at a low temperature (preferably at 0° C), then filtered at the pump, washed with cold water till the filtrate no longer gives a chlorine reaction, and dried at 100° C yield 32 g of title compound.

Introduction to the preparation of organic compounds, E. Fisher, 145-147, 1909

IUPAC Name

2,3,4,5-tetrahydroxyhexanedioic acid

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)

InChI Key

DSLZVSRJTYRBFB-UHFFFAOYSA-N

Canonical SMILES

C(C(C(C(=O)O)O)O)(C(C(=O)O)O)O

MeSH Synonyms

galactaric acid, galactaric acid, sodium salt, mucic acid, strontium galactarate mono-hydrate

Depositor-Supplied Synonyms

mucic acid, Schleimsaure, Tetrahydroxyadipic acid, Saccharolactic acid, Galactaric acid, D-, 2,3,4,5-Tetrahydroxyhexanedioic acid, hexaric acid, Galactaric-acid-, Galactosaccharic acid, NSC8127, 2,3,4,5-Tetrahydroxyadipic Acid, SBB058704, D-mannaric acid, Schleimsaure [German], Tetrahydroxyhexanedioic acid, HSDB 2116, Galacteric acid, NSC 8127, EINECS 208-404-0, BRN 1728117, NCGC00096080-01, AI3-06294, AI3-19582, d-Galactaric acid #, Spectrum_000129, Tetrahydroxy adipic acid, SpecPlus_000412, WLN: QVYQYQYQYQVQ, 12550-08-2, Spectrum2_001454, Spectrum4_001910, Spectrum5_000600, AC1L19LY, AC1Q5SR1, SCHEMBL5497, KBioGR_002506, KBioSS_000589, (2S,3R,4S,5R)-2,3,4,5-Tetrahydroxyhexane-1,6-dioic acid, DivK1c_006508, SPECTRUM1501211, SPBio_001347, CTK3J1984, KBio1_001452, KBio2_000589, KBio2_003157, KBio2_005725, DSLZVSRJTYRBFB-UHFFFAOYSA-N, NSC-8127, ANW-43751, AR-1J1861, CCG-38868, AKOS024386337, MCULE-4740161184, RTR-018679, SDCCGMLS-0066970.P001, AN-23534, CA001371, CA008734, LS-70977, NCI60_000682, TR-018679, ST51037424, 3B3-033080, A9C2B0B4-D17A-489A-A900-65FFAE0F00B6

Removed Synonyms

galactaric acid, Saccharic acid, D-glucaric acid, MTPA, GLUCARIC ACID, CID607, 526-99-8, 87-73-0, 93805-65-3

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