Levoglucosan (1,6-Anhydro-β-D-glucopyranose) is an anhydrosaccharide generated by pyrolysis of glucan and is widely found in nature.

Physicochemical Properties

Molecular Formula	C6H10O5
Molecular Weight	162.14
Exact Mass	162.052
CAS #	498-07-7
Related CAS #	Levoglucosan-d7;2483832-05-7;Levoglucosan-13C6;1375293-81-4
PubChem CID	2724705
Appearance	White to off-white solid powder
Density	1.7±0.1 g/cm3
Boiling Point	383.8±42.0 °C at 760 mmHg
Melting Point	182-184ºC
Flash Point	185.9±27.9 °C
Vapour Pressure	0.0±2.0 mmHg at 25°C
Index of Refraction	1.620
LogP	-0.04
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	0
Heavy Atom Count	11
Complexity	161
Defined Atom Stereocenter Count	5
SMILES	C1[C@@H]2[C@H]([C@@H]([C@H]([C@H](O1)O2)O)O)O
InChi Key	TWNIBLMWSKIRAT-VFUOTHLCSA-N
InChi Code	InChI=1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1
Chemical Name	(1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

ln Vitro	Burning cellulose and hemicellulose produces monosaccharide anhydrides, such as levoglucosan (1,6-anhydro-β-D-glucopyranoside; LG), mannosan, and galactosan[1].
References	[1]. Conversion of levoglucosan into glucose by the coordination of four enzymes through oxidation, elimination, hydration, and reduction. Sci Rep. 2020;10(1):20066. Published 2020 Nov 18.
Additional Infomation	Levoglucosan is a anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose. It has a role as a human metabolite, a biomarker and an Arabidopsis thaliana metabolite. Levoglucosan has been reported in Lotus burttii, Lotus tenuis, and other organisms with data available. Glucosan is a metabolite found in or produced by Saccharomyces cerevisiae.

Solubility Data

Solubility (In Vitro)

DMSO :~100 mg/mL (~616.75 mM)

Solubility (In Vivo)

Solubility in Formulation 1: ≥ 2.5 mg/mL (15.42 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (15.42 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (15.42 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	6.1675 mL	30.8375 mL	61.6751 mL
	5 mM	1.2335 mL	6.1675 mL	12.3350 mL
	10 mM	0.6168 mL	3.0838 mL	6.1675 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.