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Revision as of 11:41, 12 October 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI SMILES InChIKey UNII.← Previous edit Revision as of 11:51, 12 October 2010 edit undoCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBot|buNext edit →
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{{chembox {{chembox
⚫ | verifiedrevid = 390261638
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| 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
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| OtherNames=<small>D</small>-Glucono-1,5-lactone | OtherNames=<small>D</small>-Glucono-1,5-lactone
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = WQ29KQ9POT | UNII = WQ29KQ9POT
| 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/s1 | 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/s1
| InChIKey = PHOQVHQSTUBQQK-SQOUGZDYBO | InChIKey = PHOQVHQSTUBQQK-SQOUGZDYBO
| CASNo = 90-80-2 | CASNo = 90-80-2
| CASNo_Ref = {{cascite|??|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| EC-number = 202-016-5 | EC-number = 202-016-5
| ChemSpiderID = 6760 | ChemSpiderID = 6760

Revision as of 11:51, 12 October 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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.001.833 Edit this at Wikidata
E number E575 (acidity regulators, ...)
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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). checkY 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

  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. PMID 19506247.

See also

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