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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:02 UTC
HMDB IDHMDB0000640
Secondary Accession Numbers
  • HMDB00640
Metabolite Identification
Common NameLevoglucosan
DescriptionLevoglucosan is an anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose. It is formed from the pyrolysis of carbohydrates, such as starch and cellulose. As a result, levoglucosan is often used as a chemical tracer for biomass burning in atmospheric chemistry studies, particularly with respect to airborne particulate matter. Levoglucosan in urine has been shown to be highly correlated with regional fires and as a biomarker for wood smoke exposure (PMID: 19165390 ). This is because the gas emitted by the pyrolysis of wood (biomass) contains significant amounts of levoglucosan. The hydrolysis of levoglucosan generates the fermentable sugar glucose, and therefore lignocellulosic material exhibits great potential as a renewable feedstock for the production of bioethanol. Levoglucosan can also be utilized in the synthesis of chiral polymers such as unhydrolysable glucose polymers. Levoglucosan is also produced via caramelization of sugar. Consumption of caramel or caramel-containing sweets can lead to a short-term 5X increase in urinary levels of levoglucosan (from 20 uM/mM creatinine to 100 uM/mM creatinine) (PMID: 19707249 ). Urinary levoglucosan levels increase within 2 h of caramel consumption and return to pre-exposure levels within 24 h. These data suggest that diet is a major factor in determining urinary levoglucosan levels and that recent dietary history needs to be taken into account to use levoglucosan as a marker for wood smoke exposure. Excretory levels of levoglucosan vary widely from zero up to 5.3 mmol/L (PMID: 3757263 , 16448658 , 16317539 ).
Structure
Data?1676999702
Synonyms
ValueSource
1,6-Anhydro-beta-D-glucoseChEBI
1,6-Anhydro-beta-glucopyranoseChEBI
1,6-AnhydroglucoseChEBI
GlucosanChEBI
LeucoglucosanChEBI
1,6-Anhydro-b-D-glucoseGenerator
1,6-Anhydro-β-D-glucoseGenerator
1,6-Anhydro-b-glucopyranoseGenerator
1,6-Anhydro-β-glucopyranoseGenerator
1,6-Anhydro-b-D-glucopyranoseHMDB
1,6-Anhydro-beta-D-glucopyranoseHMDB
1,6-Anhydro-beta-delta-glucopyranoseHMDB
1,6-Anhydro-beta-delta-glucoseHMDB
1,6-Anhydro-D-glucoseHMDB
1,6-Anhydro-delta-glucoseHMDB
6,8-Dioxabicyclo[3.2.1]octane b-D-glucopyranose deriv.HMDB
6,8-Dioxabicyclo[3.2.1]octane b-delta-glucopyranose deriv.HMDB
Anhydro-D-mannosanHMDB
Anhydro-delta-mannosanHMDB
L-GlucosanHMDB
Chemical FormulaC6H10O5
Average Molecular Weight162.1406
Monoisotopic Molecular Weight162.05282343
IUPAC Name(1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
Traditional Namelevoglucosan
CAS Registry Number498-07-7
SMILES
[H][C@@]12OC[C@@H](O1)[C@@H](O)[C@H](O)[C@H]2O
InChI Identifier
InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1
InChI KeyTWNIBLMWSKIRAT-VFUOTHLCSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as oxepanes. Oxepanes are compounds containing an oxepane ring, which is a seven-member saturated aliphatic heterocycle with one oxygen and six carbon atoms.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassOxepanes
Sub ClassNot Available
Direct ParentOxepanes
Alternative Parents
Substituents
  • Oxepane
  • Oxane
  • Monosaccharide
  • Meta-dioxolane
  • Secondary alcohol
  • Oxacycle
  • Polyol
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Alcohol
  • Aliphatic heteropolycyclic compound
Molecular FrameworkAliphatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point183 °CNot Available
Boiling Point383.00 to 384.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility62.3 mg/mLNot Available
LogP-1.694 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1600 g/LALOGPS
logP-2.2ALOGPS
logP-1.8ChemAxon
logS0.99ALOGPS
pKa (Strongest Acidic)12.21ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area79.15 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity32.41 m³·mol⁻¹ChemAxon
Polarizability14.13 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.80131661259
DarkChem[M-H]-132.14131661259
AllCCS[M+H]+136.20232859911
AllCCS[M-H]-127.48332859911
DeepCCS[M-2H]-171.21230932474
DeepCCS[M+Na]+145.52630932474
AllCCS[M+H]+136.232859911
AllCCS[M+H-H2O]+131.732859911
AllCCS[M+NH4]+140.432859911
AllCCS[M+Na]+141.632859911
AllCCS[M-H]-127.532859911
AllCCS[M+Na-2H]-128.432859911
AllCCS[M+HCOO]-129.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Levoglucosan[H][C@@]12OC[C@@H](O1)[C@@H](O)[C@H](O)[C@H]2O3234.1Standard polar33892256
Levoglucosan[H][C@@]12OC[C@@H](O1)[C@@H](O)[C@H](O)[C@H]2O1465.4Standard non polar33892256
Levoglucosan[H][C@@]12OC[C@@H](O1)[C@@H](O)[C@H](O)[C@H]2O1488.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Levoglucosan,1TMS,isomer #1C[Si](C)(C)O[C@@H]1[C@H]2CO[C@H](O2)[C@H](O)[C@H]1O1479.7Semi standard non polar33892256
Levoglucosan,1TMS,isomer #2C[Si](C)(C)O[C@H]1[C@H](O)[C@H]2CO[C@H](O2)[C@@H]1O1497.0Semi standard non polar33892256
Levoglucosan,1TMS,isomer #3C[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O21495.9Semi standard non polar33892256
Levoglucosan,2TMS,isomer #1C[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C)[C@@H]2OC[C@H]1O21586.5Semi standard non polar33892256
Levoglucosan,2TMS,isomer #2C[Si](C)(C)O[C@@H]1[C@H]2CO[C@H](O2)[C@H](O)[C@H]1O[Si](C)(C)C1591.0Semi standard non polar33892256
Levoglucosan,2TMS,isomer #3C[Si](C)(C)O[C@H]1[C@H](O)[C@H]2CO[C@H](O2)[C@@H]1O[Si](C)(C)C1600.6Semi standard non polar33892256
Levoglucosan,3TMS,isomer #1C[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C)[C@H]2CO[C@H](O2)[C@@H]1O[Si](C)(C)C1702.1Semi standard non polar33892256
Levoglucosan,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@@H]1[C@H]2CO[C@H](O2)[C@H](O)[C@H]1O1718.3Semi standard non polar33892256
Levoglucosan,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H]2CO[C@H](O2)[C@@H]1O1729.6Semi standard non polar33892256
Levoglucosan,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@@H]1[C@@H](O)[C@H](O)[C@H]2CO[C@@H]1O21728.3Semi standard non polar33892256
Levoglucosan,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]2OC[C@H]1O22021.2Semi standard non polar33892256
Levoglucosan,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)O[C@@H]1[C@H]2CO[C@H](O2)[C@H](O)[C@H]1O[Si](C)(C)C(C)(C)C2004.0Semi standard non polar33892256
Levoglucosan,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O)[C@H]2CO[C@H](O2)[C@@H]1O[Si](C)(C)C(C)(C)C2021.5Semi standard non polar33892256
Levoglucosan,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H]1[C@H](O[Si](C)(C)C(C)(C)C)[C@H]2CO[C@H](O2)[C@@H]1O[Si](C)(C)C(C)(C)C2310.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Levoglucosan GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0uxr-0950000000-70ad01d41ff4333eadf92014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Levoglucosan EI-B (Non-derivatized)splash10-0uxr-0891000000-57d1cb031374b05f81ee2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Levoglucosan GC-EI-TOF (Non-derivatized)splash10-0uxr-0950000000-70ad01d41ff4333eadf92017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (Non-derivatized) - 70eV, Positivesplash10-053u-9700000000-c11d864b6822a2dd966b2016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (3 TMS) - 70eV, Positivesplash10-00dr-9565000000-6d6d0dfecd366e99e4d92017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TBDMS_1_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TBDMS_2_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TBDMS_2_3) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Levoglucosan GC-MS (TBDMS_3_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Negative-QTOFsplash10-0006-0900000000-ac847a3bb73d41f49c982012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan LC-ESI-QTOF , negative-QTOFsplash10-0006-0900000000-ac847a3bb73d41f49c982017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan 40V, Negative-QTOFsplash10-0a4l-9000000000-7bb1d2984b85d3ea59f32021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan 20V, Negative-QTOFsplash10-0ab9-9000000000-ca6ed7b53ee1e2b1f81d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan 30V, Negative-QTOFsplash10-0006-0900000000-ac847a3bb73d41f49c982021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan 10V, Negative-QTOFsplash10-0fk9-9200000000-eac1336013686b48cafc2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-9200000000-de7ea818bfd73e81bdc02012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-0ap3-9000000000-6db689252d5a1dbb66162012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-052f-9000000000-64f52041bef6f8fd63032012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive-QTOFsplash10-01qa-1900000000-bd41a8b766dc8d62c0d82012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan LC-ESI-QTOF , positive-QTOFsplash10-01qa-1900000000-bd41a8b766dc8d62c0d82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan 40V, Positive-QTOFsplash10-0006-9000000000-4f8012fb5d2fca895d062021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan 20V, Positive-QTOFsplash10-07bk-9000000000-d3f3830e72144f10cd142021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan 10V, Positive-QTOFsplash10-05n0-9100000000-bd3e5214bd96e7ff58cb2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan 20V, Positive-QTOFsplash10-0ap3-9000000000-2e6b4a130ed5624838082021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan 10V, Positive-QTOFsplash10-05n0-9100000000-8011677f551a4270ff112021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Levoglucosan 40V, Positive-QTOFsplash10-0007-9000000000-74a6c5b8f6aa28124f0b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levoglucosan 10V, Negative-QTOFsplash10-03di-0900000000-14a66c38d90a0376e8f42016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levoglucosan 20V, Negative-QTOFsplash10-03di-2900000000-2046d1a11a651e07604a2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levoglucosan 40V, Negative-QTOFsplash10-0006-9200000000-13457c8abeb48c83d2af2016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levoglucosan 10V, Negative-QTOFsplash10-03di-0900000000-2606fdba0d7add9cbef72021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levoglucosan 20V, Negative-QTOFsplash10-0bt9-9600000000-28f762ccedd56ed21a4c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levoglucosan 40V, Negative-QTOFsplash10-0006-9400000000-7a4ff35e6bf7ab7552da2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levoglucosan 10V, Positive-QTOFsplash10-03di-0900000000-3952c076838b2d8a44c12016-09-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Levoglucosan 20V, Positive-QTOFsplash10-03dj-0900000000-b09c5e74350b102ce94c2016-09-12Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
UrineDetected and Quantified52.785 +/- 91.707 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Normal
    • Analysis of 30 no...
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified10.1 (2.4-29.6) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedCancer patients undergoing total body irradiation details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
UrineDetected and Quantified19.984 +/- 17.348 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
details
UrineDetected and Quantified4.6 +/- 7.1 umol/mmol creatinineNot SpecifiedBoth
Lung cancer
details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothAutosomal dominant polycystic kidney disease (ADPKD) details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Lung Cancer
  1. Stretch C, Eastman T, Mandal R, Eisner R, Wishart DS, Mourtzakis M, Prado CM, Damaraju S, Ball RO, Greiner R, Baracos VE: Prediction of skeletal muscle and fat mass in patients with advanced cancer using a metabolomic approach. J Nutr. 2012 Jan;142(1):14-21. doi: 10.3945/jn.111.147751. Epub 2011 Dec 7. [PubMed:22157537 ]
Autosomal dominant polycystic kidney disease
  1. Gronwald W, Klein MS, Zeltner R, Schulze BD, Reinhold SW, Deutschmann M, Immervoll AK, Boger CA, Banas B, Eckardt KU, Oefner PJ: Detection of autosomal dominant polycystic kidney disease by NMR spectroscopic fingerprinting of urine. Kidney Int. 2011 Jun;79(11):1244-53. doi: 10.1038/ki.2011.30. Epub 2011 Mar 9. [PubMed:21389975 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB112163
KNApSAcK IDC00007411
Chemspider ID9587432
KEGG Compound IDNot Available
BioCyc IDCPD-12923
BiGG IDNot Available
Wikipedia LinkLevoglucosan
METLIN ID5613
PubChem Compound2724705
PDB IDNot Available
ChEBI ID30997
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1149771
References
Synthesis ReferenceTanaka, Choji. Anhydrosugars. I. Constitutions of anhydrosugars. Memoirs of the College of Science, University of Kyoto, Series A (1930), 13 239-53.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Migliaccio CT, Bergauff MA, Palmer CP, Jessop F, Noonan CW, Ward TJ: Urinary levoglucosan as a biomarker of wood smoke exposure: observations in a mouse model and in children. Environ Health Perspect. 2009 Jan;117(1):74-9. doi: 10.1289/ehp.11378. Epub 2008 Aug 15. [PubMed:19165390 ]
  2. Bergauff MA, Ward TJ, Noonan CW, Migliaccio CT, Simpson CD, Evanoski AR, Palmer CP: Urinary levoglucosan as a biomarker of wood smoke: results of human exposure studies. J Expo Sci Environ Epidemiol. 2010 Jun;20(4):385-92. doi: 10.1038/jes.2009.46. Epub 2009 Aug 26. [PubMed:19707249 ]
  3. Dorland L, Wadman SK, Fabery de Jonge H, Ketting D: 1,6-Anhydro-beta-D-glucopyranose (beta-glucosan), a constituent of human urine. Clin Chim Acta. 1986 Aug 30;159(1):11-6. [PubMed:3757263 ]
  4. Dixon RW, Baltzell G: Determination of levoglucosan in atmospheric aerosols using high performance liquid chromatography with aerosol charge detection. J Chromatogr A. 2006 Mar 24;1109(2):214-21. Epub 2006 Jan 31. [PubMed:16448658 ]
  5. Schkolnik G, Rudich Y: Detection and quantification of levoglucosan in atmospheric aerosols: a review. Anal Bioanal Chem. 2006 May;385(1):26-33. Epub 2005 Nov 30. [PubMed:16317539 ]