FComEx: Galactaric acid (PC000411)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:35 UTC

Update date

2017-01-19 02:36:22 UTC

FoodComEx ID

PC000411

FoodDB Record

FDB001205

Chemical Information

Name

Galactaric acid

Description

Present in ripe fruits of peach and pear. Formed in grapes and grape must by the action of Botrytis cinerea on galacturonic acid Galactaric acid is the dicarboxylic sugar acid resulting from oxidation glactose with dilute nitric acid. It is a substrate of galactarate O-hydroxycinnamoyltransferase [EC 2.3.1.130]. (KEGG); It forms a crystalline powder which melts at 213 °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). When heated with pyridine to 140 °C, it is converted into allommic acid. When digested with fuming hydrochloric acid for some time it is converted into a 2,5-furandicarboxylic acid (FDCA) while on heating with barium sulfide it is transformed into athiophene 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. Galactaric acid is found in many foods, some of which are alcoholic beverages, fruits, pomes, and peach.

CAS Number

526-99-8

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioate	biospider
(2R,3S,4R,5S)-2,3,4,5-tetrahydroxyhexanedioic acid	biospider
1,2,3,4-Tetrahydroxy-1,4-butanedicarboxylic acid	db_source
Acido galactarico	biospider
Acido mucico	biospider
D-Galactaric acid	HMDB
Galactarate	Generator
Galactarsaeure	ChEBI
Galactosaccharate	biospider
Galactosaccharic acid	db_source
Galaktarsaeure	ChEBI
Hexaric acid	biospider
Meso-galactaric acid	biospider
MTPA	biospider
Mucate	Generator
Mucic acid	db_source
Mucinsaeure	ChEBI
Saccharolactate	biospider
Saccharolactic acid	ChEBI
Schleimsaeure	ChEBI
Schleimsaure	HMDB
Tetrahydroxyadipic acid	db_source
Tetrahydroxyhexanedioic acid	biospider

Chemical Formula

C6H10O8

IUPAC name

2,3,4,5-tetrahydroxyhexanedioic acid

InChI Identifier

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

Isomeric SMILES

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

Average Molecular Weight

210.1388

Monoisotopic Molecular Weight

210.037567296

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Glucuronic acid derivatives

Alternative Parents