Record Information
Version2.0
Creation Date2012-05-31 10:22:01 -0600
Update Date2015-09-13 12:56:06 -0600
Secondary Accession Numbers
  • ECMDB00150
Identification
Name:Gluconolactone
Description:Gluconolactone is a lactone or oxidized derivative of glucose. Gluconolactone is a polyhydroxy acid (PHA) that is capable of chelating metals and may also function by scavenging free radicals. When dissolved in water, it 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 gluconolactone is increased by heat and high pH. It is an intermediate in glucose and glucose-1-phosphate degradation.
Structure
Thumb
Synonyms:
  • δ-gluconolactone
  • 1,5-D-Gluconolactone
  • 1,5-delta-Gluconolactone
  • 1,5-Gluconolactone
  • 1,5-δ-Gluconolactone
  • 3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-one
  • 3,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-one
  • b-glucono-1,5-Lactone
  • Beta-Glucono-1,5-Lactone
  • D(+)-Gluconate g-lactone
  • D(+)-Gluconate gamma-lactone
  • D(+)-Gluconate γ-lactone
  • D(+)-Gluconic acid g-lactone
  • D(+)-Gluconic acid gamma-lactone
  • D(+)-Gluconic acid γ-lactone
  • D-(+)-Gluconate D-lactone
  • D-(+)-Gluconate-delta lactone
  • D-(+)-Gluconate-δ lactone
  • D-(+)-Gluconic acid D-lactone
  • D-(+)-Gluconic acid-delta lactone
  • D-(+)-Gluconic acid-δ lactone
  • D-Aldonolactone
  • D-delta-Gluconolactone
  • D-Gluconate 1,5-lactone
  • D-Gluconate D-lactone
  • D-Gluconate delta-lactone
  • D-Gluconate lactone
  • D-Gluconate δ-lactone
  • D-Gluconate-1,5-lactone
  • D-Gluconate-delta-lactone
  • D-Gluconate-δ-lactone
  • D-Gluconic acid 1,5-lactone
  • D-Gluconic acid D-lactone
  • D-Gluconic acid delta-lactone
  • D-Gluconic acid lactone
  • D-Gluconic acid δ-lactone
  • D-Gluconic acid-1,5-lactone
  • D-Gluconic acid-delta-lactone
  • D-Gluconic acid-δ-lactone
  • D-Gluconic delta-lactone
  • D-Gluconic δ-lactone
  • D-glucono-δ-lactone
  • D-Glucono-1,5-lactone
  • D-Glucono-D-lactone
  • D-Glucono-delta-lactone
  • D-glucono-δ-Lactone
  • D-Gluconolactone
  • D-δ-Gluconolactone
  • Delta-(+)-Gluconate D-lactone
  • Delta-(+)-Gluconate-delta lactone
  • Delta-(+)-Gluconic acid D-lactone
  • Delta-(+)-Gluconic acid-delta lactone
  • Delta-Aldonolactone
  • Delta-D-Gluconolactone
  • Delta-delta-Gluconolactone
  • Delta-Gluconate 1,5-lactone
  • Delta-Gluconate D-lactone
  • Delta-Gluconate delta-lactone
  • Delta-Gluconate lactone
  • Delta-Gluconate-1,5-lactone
  • delta-Gluconate-delta-lactone
  • Delta-Gluconic acid 1,5-lactone
  • Delta-Gluconic acid D-lactone
  • Delta-Gluconic acid delta-lactone
  • Delta-Gluconic acid lactone
  • Delta-Gluconic acid-1,5-lactone
  • Delta-Gluconic acid-delta-lactone
  • Delta-Gluconic delta-lactone
  • Delta-Glucono-1,5-lactone
  • Delta-Glucono-delta-lactone
  • Delta-Gluconolactone
  • Fujiglucon
  • g-Gluconolactone
  • Gamma-Gluconolactone
  • Glucarolactone
  • Gluconate lactone
  • Gluconate, lactone
  • Gluconic acid lactone
  • Gluconic acid, lactone
  • Gluconic delta-lactone
  • Gluconic lactone
  • Gluconic δ-lactone
  • Glucono 1,5-lactone
  • Glucono delta lactone
  • Glucono delta-lactone
  • glucono g-Lactone
  • Glucono gamma-lactone
  • glucono γ-Lactone
  • glucono δ Lactone
  • glucono δ-Lactone
  • Glucono-δ-lactone
  • Glucono-1,5-lactone
  • Glucono-delta-lactone
  • glucono-δ-Lactone
  • Gluconolactone
  • β-glucono-1,5-Lactone
  • γ-Gluconolactone
  • δ-(+)-Gluconate D-lactone
  • δ-(+)-Gluconate-δ lactone
  • δ-(+)-Gluconic acid D-lactone
  • δ-(+)-Gluconic acid-δ lactone
  • δ-Aldonolactone
  • δ-D-Gluconolactone
  • δ-Gluconate 1,5-lactone
  • δ-Gluconate D-lactone
  • δ-Gluconate lactone
  • δ-Gluconate δ-lactone
  • δ-Gluconate-1,5-lactone
  • δ-Gluconate-δ-lactone
  • δ-Gluconic acid 1,5-lactone
  • δ-Gluconic acid D-lactone
  • δ-Gluconic acid lactone
  • δ-Gluconic acid δ-lactone
  • δ-Gluconic acid-1,5-lactone
  • δ-Gluconic acid-δ-lactone
  • δ-Gluconic δ-lactone
  • δ-glucono-1,5-Lactone
  • δ-glucono-δ-Lactone
  • δ-Gluconolactone
  • δ-δ-Gluconolactone
Chemical Formula:C6H10O6
Weight:Average: 178.14
Monoisotopic: 178.047738052
InChI Key:PHOQVHQSTUBQQK-SQOUGZDYSA-N
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/s1
CAS number:90-80-2
IUPAC Name:(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-one
Traditional IUPAC Name:gluconolactone
SMILES:OC[C@H]1OC(=O)[C@H](O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as gluconolactones. These are polyhydroxy acids containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentGluconolactones
Alternative Parents
Substituents
  • Gluconolactone
  • Delta valerolactone
  • Delta_valerolactone
  • Oxane
  • Carboxylic acid ester
  • Lactone
  • Secondary alcohol
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Oxacycle
  • Carboxylic acid derivative
  • Polyol
  • Hydrocarbon derivative
  • Organic oxide
  • Alcohol
  • Primary alcohol
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:0
Melting point:151-155 °C
Experimental Properties:
PropertyValueSource
Water Solubility:590.0 mg/mL [MERCK INDEX (1996)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility586.0 mg/mLALOGPS
logP-2.2ALOGPS
logP-2.7ChemAxon
logS0.52ALOGPS
pKa (Strongest Acidic)11.62ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area107.22 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity34.78 m3·mol-1ChemAxon
Polarizability15.63 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
  • Microbial metabolism in diverse environments ec01120
  • Pentose phosphate pathway ec00030
EcoCyc Pathways:
Concentrations
ConcentrationStrainMediaGrowth StatusGrowth SystemTemperatureDetails
1040± 0 uMK12 NCM3722Gutnick minimal complete medium (4.7 g/L KH2PO4; 13.5 g/L K2HPO4; 1 g/L K2SO4; 0.1 g/L MgSO4-7H2O; 10 mM NH4Cl) with 4 g/L glucoseMid-Log PhaseShake flask and filter culture37 oCPMID: 19561621
Find out more about how we convert literature concentrations.
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-0932000000-0b9d34fd1930d30adac9View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-005a-0920000000-48470ef74f46934597a0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014j-0950000000-483acf515b56ae5dc886View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0fvi-1952000000-f92fb779cdb5daa45f09View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-11bi-9500000000-59fc28b889280c7c2a5cView in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0fvi-1952000000-f92fb779cdb5daa45f09View in MoNA
GC-MSGC-MS Spectrum - GC-MS (4 TMS)splash10-0kki-7239300000-aa269ca53fc88c5847e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-001i-5900000000-443ab6dcdad04641cb49View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0avl-9000000000-5aba2e27767b74e7e315View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-052f-9000000000-081648ead7bc8b21d941View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01t9-0900000000-7a99fa6e5ac000ab06f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fu-3900000000-7f96bedb201e601e238eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-006x-9200000000-c51e82de843b7755c5b6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-3900000000-b80e81f6d02c1d0116a2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0adi-6900000000-590a75b51bd97402a88dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-ea7b9a23b7a07d266c68View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Friedrich T, Strohdeicher M, Hofhaus G, Preis D, Sahm H, Weiss H: The same domain motif for ubiquinone reduction in mitochondrial or chloroplast NADH dehydrogenase and bacterial glucose dehydrogenase. FEBS Lett. 1990 Jun 4;265(1-2):37-40. Pubmed: 2142103
  • Harkness RA, Purkiss P, Duffy S, Chalmers RA, Jones M: The effects of fetal energy depletion on amniotic fluid concentrations of amino acids, organic acids and related metabolites. J Inherit Metab Dis. 1988;11(1):103-13. Pubmed: 3128683
  • Hunt MJ, Barnetson RS: A comparative study of gluconolactone versus benzoyl peroxide in the treatment of acne. Australas J Dermatol. 1992;33(3):131-4. Pubmed: 1303072
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • MacNeil ML, Steinberg KK, Yeager PR, Smith SJ: A semiautomated procedure for urinary D-glucaric acid using a centrifugal analyzer. J Anal Toxicol. 1986 Jan-Feb;10(1):15-7. Pubmed: 3951202
  • Puri RN, Zhou FX, Colman RF, Colman RW: Plasmin-induced platelet aggregation is accompanied by cleavage of aggregin and indirectly mediated by calpain. Am J Physiol. 1990 Dec;259(6 Pt 1):C862-8. Pubmed: 2148055
  • Rakotomanga S, Baillet A, Pellerin F, Baylocq-Ferrier D: Simultaneous determination of gluconolactone, galactonolactone and galactitol in urine by reversed-phase liquid chromatography: application to galactosemia. J Chromatogr. 1991 Oct 4;570(2):277-84. Pubmed: 1797843
  • Steinberg KK, Needham LL: A comparison of two methods for quantifying D-glucaric acid. J Anal Toxicol. 1986 Jul-Aug;10(4):139-41. Pubmed: 3747452
  • van Weely S, Brandsma M, Strijland A, Tager JM, Aerts JM: Demonstration of the existence of a second, non-lysosomal glucocerebrosidase that is not deficient in Gaucher disease. Biochim Biophys Acta. 1993 Mar 24;1181(1):55-62. Pubmed: 8457606
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:Chu, Lijia. Technology for industrial production of d-gluconolactone. Shipin Kexue (Beijing, China) (1985), 66 13-14.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID16217
HMDB IDHMDB00150
Pubchem Compound ID7027
Kegg IDC00198
ChemSpider ID6760
WikipediaGluconolactone
BioCyc IDGLC-D-LACTONE
EcoCyc IDGLC-D-LACTONE
Ligand ExpoLGC

Enzymes

General function:
Involved in oxidoreductase activity, acting on CH-OH group of donors
Specific function:
GDH is probably involved in energy conservation rather than in sugar metabolism
Gene Name:
gcd
Uniprot ID:
P15877
Molecular weight:
86747
Reactions
D-glucose + ubiquinone = D-glucono-1,5-lactone + ubiquinol.