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Showing Compound Glucaric acid (FDB022169)

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
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
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
Physico-Chemical Properties - Experimental
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
Predicted GC-MSGlucaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TBDMS_4_14, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TBDMS_5_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TBDMS_6_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, "Glucaric acid,4TBDMS,#14" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_5, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_1_6, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_2_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSGlucaric acid, TMS_2_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-4290000000-dff4fd55a904d215586a2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0abi-9000000000-178202e29014c0d1d5942012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0ab9-9000000000-c6d132cfd1374248952d2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-0390000000-f3fdb1545009312f6a252012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-000i-9620000000-1bde5d31aa638eab1df12012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-052r-9000000000-fcfaa9b35c8d204ab0ec2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0ab9-9000000000-20e03e65e2d34a86ffba2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-0ab9-9000000000-dd03e436136ea5ad38c42012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0390000000-f3fdb1545009312f6a252017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-9620000000-1bde5d31aa638eab1df12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-052r-9000000000-fcfaa9b35c8d204ab0ec2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ab9-9000000000-20e03e65e2d34a86ffba2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0ab9-9000000000-dd03e436136ea5ad38c42017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-9310000000-bd910793555bb11fd0372017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0006-2960000000-b147e30a08581da984642017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-059i-9000000000-613b85fa3c0d461986b32021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-9310000000-ede1713559571675b04d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-9530000000-87fcd3003f686bddb9992021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9000000000-7fa748efe187f8a95a862021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-2950000000-4213fb06e5d54a446f192017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a70-8900000000-1c5b1e57a901b2c855102017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9200000000-3d6d232455d3bf96a4612017-07-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-8920000000-a1393eb5fa869e7c23f32017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-9600000000-8c43d68278949dbece7f2017-07-26View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ar9-9300000000-98861fb518fdc09acc582017-07-26View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 5%_DMSO, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)Spectrum
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
Processing...
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference