Record Information
Version1.0
Creation date2010-04-08 22:05:11 UTC
Update date2018-05-29 00:33:25 UTC
Primary IDFDB001980
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameD-Gluconic acid
DescriptionDietary supplement, acidity regulator approved in Japan. Component of bottle rinsing formulations Gluconic acid is one of the 16 stereoisomers of 2,3,4,5,6-pentahydroxyhexanoic acid. The salts of gluconic acid are known as "gluconates". Gluconic acid, gluconate salts, and gluconate esters occur widely in nature because such species arise from the oxidation of glucose. Gluconic acid occurs naturally in fruit, honey, kombucha tea, and wine. As a food additive (E574), it is an acidity regulator.
CAS Number526-95-4
Structure
Thumb
Synonyms
SynonymSource
(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acidChEBI
D-Gluco-hexonic acidChEBI
D-GluconsaeureChEBI
D-GlukonsaeureChEBI
Dextronic acidChEBI
Glycogenic acidChEBI
Hexonic acidChEBI
Maltonic acidChEBI
D-GluconateKegg
(2R,3S,4R,5R)-2,3,4,5,6-PentahydroxyhexanoateGenerator
D-Gluco-hexonateGenerator
DextronateGenerator
GlycogenateGenerator
HexonateGenerator
MaltonateGenerator
D-Gluconic acidGenerator
GluconateGenerator
2,3,4,5,6-Pentahydroxy-hexanoateHMDB
2,3,4,5,6-Pentahydroxy-hexanoic acidHMDB
2,3,4,5,6-PentahydroxyhexanoateHMDB
2,3,4,5,6-Pentahydroxyhexanoic acidHMDB
GCOHMDB
GlosantoHMDB
GlyconateHMDB
Glyconic acidHMDB
PentahydroxycaproateHMDB
Pentahydroxycaproic acidHMDB
Boron gluconateHMDB
Gluconic acid, (113)indium-labeledHMDB
Gluconic acid, calcium saltHMDB
Gluconic acid, cesium(+3) saltHMDB
Gluconic acid, lanthanum(+3) saltHMDB
Gluconic acid, sodium saltHMDB
Gluconic acid, strontium (2:1) saltHMDB
MagnerotHMDB
Manganese gluconateHMDB
Sodium gluconateHMDB
Zinc gluconateHMDB
Gluconic acid, (159)dysprosium-labeled saltHMDB
Gluconic acid, aluminum (3:1) saltHMDB
Gluconic acid, ammonium saltHMDB
Gluconic acid, magnesium (2:1) saltHMDB
Gluconic acid, (14)C-labeledHMDB
Gluconic acid, 1-(14)C-labeledHMDB
Gluconic acid, 6-(14)C-labeledHMDB
Gluconic acid, cobalt (2:1) saltHMDB
Gluconic acid, copper saltHMDB
Gluconic acid, manganese (2:1) saltHMDB
Gluconic acid, potassium saltHMDB
Gluconic acid, tin(+2) saltHMDB
Gluconic acid, zinc saltHMDB
Lithium gluconateHMDB
Magnesium gluconateHMDB
Gluconic acid, (99)technecium (5+) saltHMDB
Gluconic acid, fe(+2) salt, dihydrateHMDB
Gluconic acid, monolithium saltHMDB
Gluconic acid, monopotassium saltHMDB
Gluconic acid, monosodium saltHMDB
2,3,4,5,6-pentahydroxy-hexanoatebiospider
2,3,4,5,6-pentahydroxy-hexanoic acidbiospider
2,3,4,5,6-Pentahydroxycaproic acidbiospider
D-gluco-HexonateGenerator
D-gluco-hexonic acidbiospider
D-gluconatebiospider
D-gluconic acidbiospider
E574manual
Gluconic acidbiospider
Gluconic acid, d-biospider
Gulonic acidbiospider
Predicted Properties
PropertyValueSource
Water Solubility159 g/LALOGPS
logP-2.6ALOGPS
logP-3.4ChemAxon
logS-0.09ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area138.45 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.27 m³·mol⁻¹ChemAxon
Polarizability17.15 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC6H12O7
IUPAC name(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid
InChI IdentifierInChI=1S/C6H12O7/c7-1-2(8)3(9)4(10)5(11)6(12)13/h2-5,7-11H,1H2,(H,12,13)/t2-,3-,4+,5-/m1/s1
InChI KeyRGHNJXZEOKUKBD-SQOUGZDYSA-N
Isomeric SMILESOC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O
Average Molecular Weight196.1553
Monoisotopic Molecular Weight196.058302738
Classification
Description belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Gluconic_acid
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Alpha-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Hydroxy acid
  • Monosaccharide
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Polyol
  • Monocarboxylic acid or derivatives
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 36.74%; H 6.17%; O 57.10%DFC
Melting PointMp 130-132°DFC
Boiling PointNot Available
Experimental Water Solubility316 mg/mL at 25 oCMERCK INDEX (1996)
Experimental logPNot Available
Experimental pKapKa 3.76 (17°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D -6.7 -> +11.7 (H2O, 5 d)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-0932000000-202af87cea2d1f7184abView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-005a-0920000000-2308d9356bc5bb01420eView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014j-0950000000-61ab7adf15e353df4ba2View in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0le9-1964000000-5eb7d6777170e1ad5fa0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0932000000-202af87cea2d1f7184abView in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0le9-1964000000-5eb7d6777170e1ad5fa0View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-0931000000-b07fcc4ac1e6701d32c8View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0fr2-0930000000-181f7b697b591cf8080bView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-06tu-9500000000-ebe398c88f74bb51e702View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positivesplash10-03fr-6121297000-698854fa2453487a1d69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-06vj-1900000000-78e4a5d92be678c068e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03ds-5900000000-f5d8284baa473ce9d77fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-014i-9500000000-7c5b20eef98d0e3d6cbbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-b2632ca9154cc5e44438View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-002b-5900000000-4a3066f9dfd6653682fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-50f63dfd017a8380a47cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-056r-9000000000-91ccf7c8949c1c9d852aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0a6r-9000000000-6e40f1cebd8b460016b3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-b2632ca9154cc5e44438View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-002b-5900000000-cf9b480ac397acfebc71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-eca61f6a9c0f1d06e84dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-056r-9000000000-91ccf7c8949c1c9d852aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a6r-9000000000-6e40f1cebd8b460016b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004j-2900000000-42150530e3232b66059bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9500000000-763d7b03787732284c19View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-9100000000-040569af699927ca6859View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-05ic-9800000000-3571d4f2ff79bc0d7fa0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-052r-9400000000-3cb207fadbe1fcae5cb7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-8c900935a94065d0938bView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
ChemSpider ID10240
ChEMBL IDCHEMBL464345
KEGG Compound IDC00257
Pubchem Compound ID10690
Pubchem Substance IDNot Available
ChEBI ID33198
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00625
CRC / DFC (Dictionary of Food Compounds) IDCBW08-O:CBW09-P
EAFUS ID1491
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDC00007303
HET IDGCO
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGluconic_acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Probable gluconokinaseIDNKQ5T6J7
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference