Levoglucosan (CHEM021693)

Record Information
Version1.0
Creation Date2016-05-25 18:10:12 UTC
Update Date2026-04-04 19:36:53 UTC
Accession NumberCHEM021693
Identification
Common NameLevoglucosan
ClassSmall Molecule
Description
A anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose.
Contaminant Sources
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
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 Mass162.141 g/mol
Monoisotopic Mass162.053 g/mol
CAS Registry Number498-07-7
IUPAC Name(1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
Traditional Namelevoglucosan
SMILES[H][C@@]12OC[C@@H](O1)[C@@H](O)[C@H](O)[C@H]2O
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted 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
Spectra
Spectra
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDHMDB0000640
FooDB IDFDB112163
Phenol Explorer IDNot Available
KNApSAcK IDC00007411
BiGG IDNot Available
BioCyc IDCPD-12923
METLIN ID5613
PDB IDNot Available
Wikipedia LinkLevoglucosan
Chemspider ID9587432
ChEBI ID30997
PubChem Compound ID2724705
Kegg Compound IDNot Available
YMDB IDYMDB02300
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=16317539
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=16448658
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=17439666
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=19165390
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3757263
6. Tanaka, Choji. Anhydrosugars. I. Constitutions of anhydrosugars. Memoirs of the College of Science, University of Kyoto, Series A (1930), 13 239-53.
7. 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.
8. 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.
9. 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.
10. 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.
11. 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.