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 | |
3D model (JSmol)
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80998 | |
ChEBI | |
ChemSpider | |
ECHA InfoCard | 100.007.142 |
EC Number |
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MeSH | 1,6-Anhydro-beta-glucopyranose |
PubChem CID
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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) |
Boiling point | 384 °C (723 °F; 657 K) |
log P | -0.04 (predicted) |
Vapor pressure | 24.1 μPa (predicted) |
Hazards | |
Flash point | 185.9 °C (366.6 °F) (predicted) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Levoglucosan (C6H10O5) is an organic compound with 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.
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 be utilized in the synthesis of chiral polymers such as unhydrolysable glucose polymers.
References
- ^ Lakshmanan, Chambra M.; Hoelscher, Harold E. (1970). "Production of Levoglucosan by Pyrolysis of Carbohydrates. Pyrolysis in Hot Inert Gas Stream". Industrial & Engineering Chemistry Product Research and Development. 9: 57. doi:10.1021/i360033a011.
- ^ Aiken, A. C.; De Foy, B.; Wiedinmyer, C.; Decarlo, P. F.; Ulbrich, I. M.; Wehrli, M. N.; Szidat, S.; Prevot, A. S. H.; Noda, J. (2010). "Mexico city aerosol analysis during MILAGRO using high resolution aerosol mass spectrometry at the urban supersite (T0) – Part 2: Analysis of the biomass burning contribution and the non-fossil carbon fraction". Atmospheric Chemistry and Physics. 10 (12): 5315. doi:10.5194/acp-10-5315-2010.
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