Levoglucosan
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| Names | |
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IUPAC name
(1R,2S,3S,4R,5R)-6,8-Dioxabicyclo[3.2.1]octane-2,3,4-triol
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| Other names
1,6-Anhydro-beta-glucopyranose Leucoglucosan
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| Identifiers | |
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3D model (JSmol)
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| 80998 | |
| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.007.142 |
| EC Number | 207-855-0 |
| MeSH | 1,6-Anhydro-beta-glucopyranose |
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PubChem CID
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| Properties | |
| C6H10O5 | |
| Molar mass | 162.14 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) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
Levoglucosan (C6H10O5) is an organic compound with a six-carbon ring structure 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. Along with other tracers such as potassium, oxalate, and gaseous acetonitrile, 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. 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".
The hydrolysis of levoglucosan generates the fermentable sugar glucose. Levoglucosan can be utilized in the synthesis of chiral polymers such as unhydrolysable glucose polymers.
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Wikipedia