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C o n t r i b u t e
● H e l p ● L e a r n t o e d i t ● C o m m u n i t y p o r t a l ● R e c e n t c h a n g e s ● U p l o a d f i l e
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( T o p )
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● ت ۆ ر ک ج ه ● Č e š t i n a ● D e u t s c h ● ف ا ر س ی ● F r a n ç a i s ● M a g y a r ● 日 本 語 ● P o l s k i ● С р п с к и / s r p s k i ● S r p s k o h r v a t s k i / с р п с к о х р в а т с к и ● T i ế n g V i ệ t ● 中 文
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P r i n t / e x p o r t
● D o w n l o a d a s P D F ● P r i n t a b l e v e r s i o n
I n o t h e r p r o j e c t s
● W i k i m e d i a C o m m o n s
A p p e a r a n c e
F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
D [1] [2] [3]
Names
IUPAC name
D
Systematic IUPAC name
(3 R S S R [2]
Identifiers
CAS Number
3D model (JSmol )
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.001.833
EC Number
E number E575 (acidity regulators, ...)
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA )
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/s1 Y
Key: PHOQVHQSTUBQQK-SQOUGZDYSA-N Y
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
Key: PHOQVHQSTUBQQK-SQOUGZDYBO
C([C@@H]1[C@H]([C@@H]([C@H](C(=O)O1)O)O)O)O
Properties
Chemical formula
C 6 H 10 O 6
Molar mass
−1
Melting point
150–153 °C (302–307 °F; 423–426 K )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound
Glucono-delta-lactone (GDL ), also known as gluconolactone, is an organic compound with the formula (HOCH)3 2 CH )CO2 . A colorless solid, it is an oxidized derivative of glucose.
It is typically produced by the aerobic oxidation of glucose in the presence of the enzyme glucose oxidase . The conversion cogenerates hydrogen peroxide , which is often the key product of the enzyme:
C 6 H 12 O 6 2 6 H 10 O 6 2 O 2
Gluconolactone spontaneously hydrolyzes to gluconic acid :[4]
C 6 H 10 O 6 2 6 H 12 O 7
Applications
[ edit ]
Gluconolactone is a food additive with the E-number E575[5] sequestrant , an acidifier ,[6] curing , pickling , or leavening agent . It is a lactone of D gluconic acid . Pure GDL is a white odorless crystalline powder.
GDL has been marketed for use in feta cheese .[7] sourness of citric acid . It is metabolized to 6-phospho-D-gluconate ; 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 [8]
The yeast Maudiozyma bulderi can be used to ferment gluconolactone to ethanol and carbon dioxide. The pH value greatly affects culture growth. Gluconolactone at 1 or 2% in a mineral media solution causes the pH to drop below 3.[9]
It is also a complete inhibitor of the enzyme amygdalin beta-glucosidase at concentrations of 1 mM.[10]
See also
[ edit ]
References
[ edit ]
^ Beil. 18
^ Wong, Chun Ming; Wong, Kwun Hei; Chen, Xiao Dong (2008). "Glucose oxidase: Natural Occurrence, Function, Properties and Industrial Applications". Applied Microbiology and Biotechnology . 78 6 ): 927–938. doi :10.1007/s00253-008-1407-4 . PMID 18330562 . S2CID 2246466 .
^ "Current EU approved additives and their E Numbers" . Food Standards Agency . Archived from the original on 22 April 2022.
^ Martin, F.; Cayot, N.; Marin, A.; et al. (2009). "Effect of oxidoreduction potential and of gas bubbling on rheological properties and microstructure of acid skim milk gels acidified with glucono-δ-lactone" (PDF) . Journal of Dairy Science . 92 12 ): 5898–5906. doi :10.3168/jds.2009-2491 PMID 19923593 . Archived (PDF) from the original on 2020-03-11. Retrieved 2019-08-16 .
^ Blythman, Joanna (21 February 2015). "Inside the food industry: the surprising truth about what you eat" . The Guardian . Archived from the original on 13 August 2016. Retrieved 28 October 2016 . {{cite web }}: CS1 maint: bot: original URL status unknown (link )
^ 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 .
^ Van Dijken, J. P.; Van Tuijl, A.; Luttik, M. A.; Middelhoven, W. J.; Pronk, J. T. (2002). "Novel pathway for alcoholic fermentation of delta-gluconolactone in the yeast Saccharomyces bulderi" . Journal of Bacteriology . 184 (3 ): 672–678. doi :10.1128/JB.184.3.672-678.2002 . PMC 139522 PMID 11790736 .
^ Petruccioli, M.; Brimer, L.; Cicalini, A. R.; Federici, F. (1999). "Production and Properties of the Linamarase and Amygdalase Activities of Penicillium aurantiogriseum P35" . Bioscience, Biotechnology, and Biochemistry . 63 5 ): 805–812. doi :10.1271/bbb.63.805 PMID 10380623 .
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Glucono_delta-lactone&oldid=1230887229 " C a t e g o r i e s : ● F o o d a c i d i t y r e g u l a t o r s ● C u r i n g a g e n t s ● D e l t a - l a c t o n e s ● P i c k l i n g a g e n t s ● L e a v e n i n g a g e n t s ● S e q u e s t r a n t s ● G a r d e m a n g e r ● T e t r a h y d r o p y r a n s ● E - n u m b e r a d d i t i v e s H i d d e n c a t e g o r i e s : ● C S 1 m a i n t : b o t : o r i g i n a l U R L s t a t u s u n k n o w n ● A r t i c l e s w i t h c h a n g e d E B I i d e n t i f i e r ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● E n u m b e r f r o m W i k i d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 2 5 J u n e 2 0 2 4 , a t 0 7 : 3 7 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
