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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
Thumb
Synonyms
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
Predicted Chromatographic Properties
Spectra
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)Not Available
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 ]