Difference between revisions of "Glucono delta-lactone"

Latest revision as of 19:18, 21 September 2010

D-Gluconic acid δ-lactone[1][2]
File:Glucono-delta-lactone-2D-skeletal.png	File:D-glucono-delta-lactone-3D-balls.png
IUPAC name (3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one
Other names D-Glucono-1,5-lactone
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number	90-80-2 Y
PubChem	736
ChemSpider	6760
EC-number	202-016-5
SMILES	Script error: No such module "collapsible list".
InChI	Script error: No such module "collapsible list".
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula	C6H10O6
Molar mass	178.14 g mol−1
Y (what is this?)  (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Glucono delta-lactone (GDL) E575^{[citation needed]} is a naturally-occurring food additive used as a sequestrant, an acidifier, or a curing, pickling, or leavening agent^{[citation needed]}. 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^{[citation needed]}. 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.^[3]

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.^[4][5]

References

See also

• Acceptable daily intake
• Glucuronolactone
• International Programme on Chemical Safetyde:Glucono-1,5-lacton

fr:Glucono delta-lactone hu:Glukono-delta-lakton ja:グルコノラクトン

1. ↑ Budavari, Susan, ed. (2001), The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (13th ed.), Merck, ISBN 0911910131 , 4469.
2. ↑ Beil. 18, V, 5, 11
3. ↑ 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. 
4. ↑ "Glucose yields sweet pest control - The Scientist".  100405 the-scientist.com
5. ↑ 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 Freely accessible. PMID 19506247.