Levoglucosan (C6H10O5) is an organic compound with a six-carbon ring structure formed from the pyrolysis of carbohydrates, such as starch and cellulose.[1] 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. 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.
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| 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 |
| EC Number |
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| MeSH | 1,6-Anhydro-beta-glucopyranose |
PubChem CID | |
| UNII | |
CompTox Dashboard (EPA) | |
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| 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 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 glucose. Levoglucosan can be utilized in the synthesis of chiral polymers such as unhydrolysable glucose polymers.