Glucaric acid

Structural formula
General
Surname	Glucaric acid
other names	(2 S , 3 S , 4 S , 5 R ) -2,3,4,5-tetrahydroxyhexane-1,6-diacid (2 S , 3 S , 4 S , 5 R ) -2,3,4,5-tetrahydroxyadipic acid D -glucaric acid ( IUPAC ) Saccharic acid (obsolete) Sugar acid (technical)
Molecular formula	C 6 H 10 O 8
Brief description	colorless needles
External identifiers / databases
CAS number 87-73-0 EC number 201-768-1 ECHA InfoCard 100.001.608 PubChem 33037 ChemSpider 30577 DrugBank DB03603 Wikidata Q424636
properties
Molar mass	210.14 g mol −1
Physical state	firmly
Melting point	126 ° C
solubility	Easily soluble in water and ethanol sparingly soluble in diethyl ether
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 228-314 P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

The D -Glucarsäure is a poly hydroxy dicarboxylic acid (see Fischer projection of stereo isomerism ), it is one of the aldaric . Technical glucaric acid is usually also referred to as sugar acid (in the narrower sense) (see also sugar acids in the broader sense). Their salts and esters are called glucarates or technically saccharates (but see sugar esters ).

It is optically active ; aqueous solutions of glucaric acid show the phenomenon of mutarotation .

Manufacturing

Glucaric acid by oxidation of D - glucose , sucrose or starch with concentrated nitric acid produced.

Occurrence

Bunch of grapes with berries of a white grape variety

Glucaric acid comes from a branch of the ascorbic acid synthesis and occurs in fruits and vegetables such as bean sprouts , buckthorn plants , grapes , apples and grapefruits .

use

It is occasionally used as a complexing agent. Your 4-lactone is a strong glucuronidase - inhibitor . The use of glucaric acid as a raw material for the chemical industry is currently being intensively worked on in applied research (white biotechnology).

See also

• Sugar acid (disambiguation)
• Gluconic acid
• Glucuronic acid
• Glutaric acid

Individual evidence

1. ↑ ^{a b c} J. Falbe, M. Regitz (Ed.): Römpp Lexikon Chemie. Volume 2: Cm-G. 10th edition. Thieme, Stuttgart / New York 1997, ISBN 3-13-734710-6 , p. 1559.
2. ^ ^{A b} David R. Lide: CRC Handbook of Chemistry and Physics . 85th edition. CRC Press, 2005, chap. 3, p. 292.
3. ↑ There is not yet a harmonized classification for this substance . A labeling of D-glucaric acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was retrieved on November 5, 2019, is reproduced from a self-classification by the distributor .
4. ↑ Thomas Haas, Arne Skerra: White biotechnology - innovation for the chemical industry. In: News from chemistry. 56 (10), 2008, pp. 1028-1031, doi: 10.1002 / nadc.200859772 .