Glucono-δ-lactone: Difference between revisions

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	\| verifiedrevid = ~~390261638~~		\| verifiedrevid = 396142714
	\| Reference = <ref>{{Merck13th\|4469}}.</ref><ref>Beil. '''18''', V, 5, 11</ref>		\| Reference = <ref>{{Merck13th\|4469}}.</ref><ref>Beil. '''18''', V, 5, 11</ref>
	\| Name = <small>D</small>-Gluconic acid δ-lactone		\| Name = <small>D</small>-Gluconic acid δ-lactone

Revision as of 15:52, 11 November 2010

D-Gluconic acid δ-lactone

Names

IUPAC name (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one

Other names D-Glucono-1,5-lactone

Identifiers

CAS Number

90-80-2

3D model (JSmol)

Interactive image

ChemSpider

6760

ECHA InfoCard

100.001.833

E number

E575 (acidity regulators, ...)

PubChem CID

UNII

WQ29KQ9POT

CompTox Dashboard (EPA)

DTXSID0026549

InChI

InChI=1S/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1Key: PHOQVHQSTUBQQK-SQOUGZDYSA-N
InChI=1/C6H10O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-5,7-10H,1H2/t2-,3-,4+,5-/m1/s1Key: PHOQVHQSTUBQQK-SQOUGZDYBO

SMILES

C(1(((C(=O)O1)O)O)O)O

Properties

Chemical formula

C₆H₁₀O₆

Molar mass

178.140 g·mol

Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).

Y verify (what is ?) Infobox references

Chemical compound

Glucono delta-lactone (GDL) E575 is a naturally-occurring food additive used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent . It is a lactone (cyclic ester) of D-gluconic acid. Pure GDL is a white odorless crystalline powder.

GDL is commonly found in honey, fruit juices, and wine . GDL is neutral, but hydrolyses in water to gluconic acid which is acidic, adding a tangy taste to foods, though it has roughly a third of the sourness of citric acid. It is metabolized to glucose; one gram of GDL yields roughly the same amount of metabolic energy as one gram of sugar.

Upon addition to water, GDL is partially hydrolysed to gluconic acid, with the balance between the lactone form and the acid form established as a chemical equilibrium. The rate of hydrolysis of GDL is increased by heat and high pH.

GDL may also be useful in controlling termites by weakening their immune system. Termites use GNBP-2 to detect and degrade carbohydrates on the surface of microbes. GDL attaches to a crucial pocket on GNBP-2 adjacent to parts of the protein that aid in breaking down microbial polysaccharides.

References

Budavari, Susan, ed. (2001). The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th ed.). Merck. ISBN 0911910131., 4469.
Beil. 18, V, 5, 11
Pocker, Y.; Green, Edmond (1973). "Hydrolysis of D-Glucono-δ-lactone. I. General Acid–Base Catalysis, Solvent Deuterium Isotope Effects, and Transition State Characterization". J. Am. Chem. Soc. 95 (1): 113–19. doi:10.1021/ja00782a019. PMID 4682891.
"Glucose yields sweet pest control - The Scientist". 100405 the-scientist.com
Bulmer, MS; Bachelet, I; Raman, R; Rosengaus, RB; Sasisekharan, R (2009). "Targeting an antimicrobial effector function in insect immunity as a pest control strategy". Proceedings of the National Academy of Sciences of the United States of America. 106 (31): 12652–7. doi:10.1073/pnas.0904063106. PMC 2722268. PMID 19506247.

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