Levoglucosan

Levoglucosan
Names
	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
CAS Number	498-07-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	80998
ChEBI	CHEBI:30997;
ChemSpider	9587432 ;
ECHA InfoCard	100.007.142
EC Number	207-855-0;
MeSH	1,6-Anhydro-beta-glucopyranose
PubChem CID	2724705;
CompTox Dashboard (EPA)	DTXSID90904321 ;
	InChI InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2 Key: TWNIBLMWSKIRAT-UHFFFAOYSA-N ;
	SMILES OC1C2COC(O2)C(O)C1O;
Properties
Chemical formula	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). Infobox references

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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

[1] 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.

[2] 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.{{cite journal}}: CS1 maint: unflagged free DOI (link)

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