Synthesis of saccharic acid (glucaric acid)

Preparation of saccharic acid

Preparation of saccharic acid (glucaric acid)

Preparation of saccharic acid (glucaric acid)

50 g of anhydrous glucose is heated on water bath with constant stirring with 350 g of nitric acid (d=1.15) until a syrupy residue remains. Obtained residue is dissolved it in a little water and evaporated until the mass begins to turn brown. The brown mass is dissolved in 150 ml of water and neutralized with a concentrated solution of potassium carbonate. Then 25 ml of 50% acetic acid is added and the solution is concentrated to about 80 ml. On standing in the cold or by rubbing, the saccharic acid potassium salt crystallizes and is kept for 12 hours at room temperature. The the crystals are filtered, wash with a little cold water and recrystallize from the least possible quantity of hot water with the addition of activated charcoal. The saccharic acid potassium salt so obtained is colorless and should be free from oxalic acid. The final yield of saccharic acid potassium salt is about 15 grams. The saccharic acid potassium salt could be converted to saccharic acid by neutralizing with streochemical amount of  hydrochloric acid.

A Class-Book of Organic Chemistry, by J. B. Cohen, 38-39, 1919

IUPAC Name

(2S,3S,4S,5R)-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)/t1-,2-,3-,4+/m0/s1

InChI Key

DSLZVSRJTYRBFB-LLEIAEIESA-N

Canonical SMILES

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

Isomeric SMILES

[C@H]([C@@H]([C@@H](C(=O)O)O)O)([C@H](C(=O)O)O)O

MeSH Synonyms

Acid, Saccharic, Anhydrous Calcium Glucarate, Anhydrous Calcium Saccharate, Calcium Glucarate, Calcium Glucarate, Anhydrous, Calcium Saccharate, Calcium Saccharate Anhydrous, Calcium Saccharate Tetrahydrate, Calcium Saccharate, Anhydrous, D Glucaric Acid, D Saccharic Acid, D-Glucaric Acid, D-Saccharic Acid, Glucarate, Anhydrous Calcium, Glucarate, Calcium, Glucaric Acid, Glucosaccharic Acid, L Gularic Acid, L-Gularic Acid, Levo Gularic Acid, Levo-Gularic Acid, Saccharate Tetrahydrate, Calcium, Saccharate, Anhydrous Calcium, Saccharate, Calcium, Saccharic Acid, Tetrahydrate, Calcium Saccharate, Tetrahydroxyadipic Acid

Depositor-Supplied Synonyms

D-glucaric acid, Saccharic acid, GLUCARIC ACID, D-glucarate, L-gularic acid, D-saccharic acid, D-glucosaccharic acid, Glucosaccharic acid, DL-Glucaric acid, glucarate, D-(+)-saccharic acid, UNII-QLZ991V4A2, 87-73-0, D-saccharate, (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid, (2S,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanedioic acid, 25525-21-7, GKR, L-gularate, (2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioate, D-glucosaccharate, D-tetrahydroxyadipate, D-(+)-saccharate, GLUCARICACID, D-tetrahydroxyadipic acid, AC1Q5QUA, bmse000239, AC1L1OW2, SCHEMBL5496, QLZ991V4A2, CHEBI:16002, HMDB00663, DSLZVSRJTYRBFB-LLEIAEIESA-N, EINECS 201-768-1, LMFA01170108, AN-42399, AN-46030, SC-15948, 2S,3S,4S,5R-tetrahydroxy-hexanedioic acid, FT-0690188, C00818, 52B6CA34-55ED-41A0-BE2A-45AABDC4DC81, 57030-41-8

Removed Synonyms

Acid, Saccharic, Calcium glucarate, D Glucaric Acid, L Gularic Acid, Tetrahydroxyadipic acid, D Saccharic Acid, Levo Gularic Acid, Levo-Gularic Acid, Glucarate, Calcium, Saccharate, Calcium, CALCIUM SACCHARATE, Anhydrous Calcium Glucarate, Anhydrous Calcium Saccharate, Calcium Saccharate Anhydrous, Calcium Glucarate, Anhydrous, Glucarate, Anhydrous Calcium, Calcium Saccharate, Anhydrous, Saccharate, Anhydrous Calcium, Calcium saccharate tetrahydrate, Saccharate Tetrahydrate, Calcium, Tetrahydrate, Calcium Saccharate, CID33037, D005937

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