Record Information
Version1.0
Creation date2011-09-21 00:09:28 UTC
Update date2020-09-17 15:42:28 UTC
Primary IDFDB022169
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameGlucaric acid
DescriptionGlucaric acid, also known as D-saccharic acid, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucaric acid is very soluble in water, and relatively neutral. Glucaric acid exists in all living organisms, ranging from bacteria to humans. In mammals, D-glucaric acid is an end product of the D-glucuronic acid pathway. The glucuronic acid pathway catalyzes the conversion of glucose to glucuronic acid, ascorbic acid, and pentoses. Like the pentose phosphate pathway, this pathway provides biosynthetic precursors and inter-converts some less common sugars to ones that can be metabolized. D-glucaric acid is particularly abundant in fruits and vegetables, with the highest concentrations found in grapefruits, apples, oranges, and cruciferous vegetables. The D-glucaric acid content in fruits and vegetables ranges from about 0.1 g/kg in grapes and lettuce to about 3.5 g/kg in apples and broccoli. Glucaric acid is available as a dietary supplement in the form of calcium D-glucarate and has been studied for therapeutic purposes including cholesterol reduction and cancer chemotherapy (PMID: 12747003; PMID: 18772850). Industrially, D-glucaric acid produced from oxidizing D-glucose has been successfully utilized to produce a hydroxylated nylon, resulting in a presumably biodegradable nylon fiber. Glucaric acid’s sodium salt is used in dishwasher detergents. The acid acts as a chelating agent that ties up the hard-water calcium and magnesium ions to make the detergents more efficient. Glucaric acid is also a powerful corrosion inhibitor and is used in many applications where water contacts metal surfaces.
CAS Number25525-21-7
Structure
Thumb
Synonyms
SynonymSource
D-(+)-Saccharic acidChEBI
D-Glucosaccharic acidChEBI
D-Saccharic acidChEBI
L-Gularic acidChEBI
Saccharic acidChEBI
D-Glucaric acidKegg
GlucarateKegg
D-(+)-SaccharateGenerator
D-GlucosaccharateGenerator
D-SaccharateGenerator
L-GularateGenerator
SaccharateGenerator
D-GlucarateGenerator
(2R,3S,4S,5S)-2,3,4,5-TetrahydroxyhexanedioateHMDB
(2R,3S,4S,5S)-2,3,4,5-Tetrahydroxyhexanedioic acidHMDB
D-TetrahydroxyadipateHMDB
D-Tetrahydroxyadipic acidHMDB
DL-Glucaric acidHMDB
GKRHMDB
Glucosaccharic acidHMDB
Tetrahydroxyadipic acidHMDB
Acid, saccharicHMDB
Anhydrous calcium glucarateHMDB
Anhydrous calcium saccharateHMDB
Calcium saccharateHMDB
Glucarate, calciumHMDB
Levo gularic acidHMDB
Levo-gularic acidHMDB
Tetrahydrate, calcium saccharateHMDB
Calcium glucarateHMDB
Calcium glucarate, anhydrousHMDB
Calcium saccharate anhydrousHMDB
Calcium saccharate, anhydrousHMDB
D Glucaric acidHMDB
Saccharate tetrahydrate, calciumHMDB
Saccharate, calciumHMDB
Calcium saccharate tetrahydrateHMDB
D Saccharic acidHMDB
Glucarate, anhydrous calciumHMDB
L Gularic acidHMDB
Saccharate, anhydrous calciumHMDB
(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioatehmdb
(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acidhmdb
D-(+)-saccharatehmdb
D-glucosaccharatehmdb
D-saccharatehmdb
D-tetrahydroxyadipatehmdb
D-tetrahydroxyadipic acidhmdb
DL-glucaric acidhmdb
L-gularatehmdb
Predicted Properties
PropertyValueSource
Water Solubility63.1 g/LALOGPS
logP-1.8ALOGPS
logP-3.1ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)2.83ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area155.52 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.14 m³·mol⁻¹ChemAxon
Polarizability16.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC6H10O8
IUPAC name(2R,3S,4S,5S)-2,3,4,5-tetrahydroxyhexanedioic acid
InChI IdentifierInChI=1S/C6H10O8/c7-1(3(9)5(11)12)2(8)4(10)6(13)14/h1-4,7-10H,(H,11,12)(H,13,14)/t1-,2-,3-,4+/m0/s1
InChI KeyDSLZVSRJTYRBFB-LLEIAEIESA-N
Isomeric SMILESO[C@@H]([C@H](O)[C@@H](O)C(O)=O)[C@H](O)C(O)=O
Average Molecular Weight210.1388
Monoisotopic Molecular Weight210.037567296
Classification
Description Belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentGlucuronic acid derivatives
Alternative Parents
Substituents
  • Glucuronic acid or derivatives
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Polyol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-00kb-0951000000-900f03a7c305b77327a7Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0931000000-0b5da9d9795e377e2131Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-000w-0934000000-065f1d82bf37b3646812Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-000t-0933000000-88564b1ce0ddb6a8ab41Spectrum
GC-MSGlucaric acid, 6 TMS, GC-MS Spectrumsplash10-001l-0988100000-b295a3efe00c6ac42fb9Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-000w-0934000000-065f1d82bf37b3646812Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-001l-0988100000-b295a3efe00c6ac42fb9Spectrum
GC-MSGlucaric acid, non-derivatized, GC-MS Spectrumsplash10-000t-0923000000-6490a1c6d0dfb83df0a3Spectrum
Predicted GC-MSGlucaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05bf-9400000000-5d870077c657dc484d46Spectrum
Predicted GC-MSGlucaric acid, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00b9-6011394000-83b916b3001ad13cf34dSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-4290000000-dff4fd55a904d215586aSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0abi-9000000000-178202e29014c0d1d594Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0ab9-9000000000-c6d132cfd1374248952dSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0390000000-f3fdb1545009312f6a25Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9620000000-1bde5d31aa638eab1df1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052r-9000000000-fcfaa9b35c8d204ab0ecSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0ab9-9000000000-20e03e65e2d34a86ffbaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0ab9-9000000000-dd03e436136ea5ad38c4Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0390000000-f3fdb1545009312f6a25Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9620000000-1bde5d31aa638eab1df1Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052r-9000000000-fcfaa9b35c8d204ab0ecSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ab9-9000000000-20e03e65e2d34a86ffbaSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ab9-9000000000-dd03e436136ea5ad38c4Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9310000000-bd910793555bb11fd037Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-2960000000-b147e30a08581da98464Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-2950000000-4213fb06e5d54a446f19Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-8900000000-1c5b1e57a901b2c85510Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9200000000-3d6d232455d3bf96a461Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-8920000000-a1393eb5fa869e7c23f3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9600000000-8c43d68278949dbece7fSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar9-9300000000-98861fb518fdc09acc58Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
2D NMR[1H,1H] 2D NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID30577
ChEMBL IDNot Available
KEGG Compound IDC00818
Pubchem Compound ID33037
Pubchem Substance IDNot Available
ChEBI ID17301
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00663
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID35926
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGlucaric 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
UDP-glucuronosyltransferase 2B4UGT2B4P06133
UDP-glucuronosyltransferase 1-4UGT1A4P22310
UDP-glucuronosyltransferase 2B7UGT2B7P16662
UDP-glucuronosyltransferase 1-1UGT1A1P22309
UDP-glucuronosyltransferase 1-9UGT1A9O60656
UDP-glucuronosyltransferase 1-6UGT1A6P19224
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference