Levoglucosan

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Levoglucosan
Stereo skeletal formula of levoglucosan
Names
Preferred IUPAC name
(1R,2S,3S,4R,5R)-6,8-Dioxabicyclo[3.2.1]octane-2,3,4-triol
Other names
1,6-Anhydro-beta-glucopyranose
Leucoglucosan
Identifiers
3D model (
JSmol
)
80998
ChEBI
ChemSpider
ECHA InfoCard
 100.007.142 Edit this at Wikidata
EC Number
  • 207-855-0
MeSH 1,6-Anhydro-beta-glucopyranose
UNII
  • InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2 checkY
    Key: TWNIBLMWSKIRAT-UHFFFAOYSA-N checkY
  • OC1C2COC(O2)C(O)C1O
Properties
C6H10O5
Molar mass 162.141 g·mol−1
Appearance Colorless crystals
Density 1.688 g·cm−3 (predicted)
Melting point 182 to 184 °C (360 to 363 °F; 455 to 457 K)
Boiling point 384 °C (723 °F; 657 K) predicted
log P -0.04 (predicted)
Vapor pressure 24.1 μPa (predicted)
Hazards
Flash point 185.9 °C (366.6 °F; 459.0 K) (predicted)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Levoglucosan (C6H10O5) is an

airborne particulate matter
. Along with other tracers such as potassium, oxalate, and gaseous acetonitrile,[2] levoglucosan has been shown to be highly correlated with regional fires. This is because the gas emitted by the pyrolysis of wood (biomass) contains significant amounts of levoglucosan.

Levoglucosan has been described as "an unequivocal biomass burning tracer" in the context of forest and brush fires.[3] But the anhydrosugar has only been found detectable in low temperature samples (150-350 °C), meaning that its value as an indicator for smoke from controlled biomass combustion in, for instance, modern domestic wood stoves which operate at temperatures above 500 °C, is "very doubtful".[4] Levoglucosan is a marker for coal combustion as well as wood.[5]

The hydrolysis of levoglucosan generates the fermentable sugar

unhydrolysable glucose polymers
.

References

  1. doi:10.1021/i360033a011
    .
  2. doi:10.5194/acp-10-5315-2010
    .
  3. ^ "Identification of biomass burning tracers" (PDF). Euro 'Milestone' Survey. Retrieved 20 March 2015.
  4. doi:10.1016/j.atmosenv.2013.08.026
    .
  5. PMID 29244948
    .
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