LEVOGLUCOSENONE Chemical Properties

alpha 

D25 -460° (c = 1.0 in CHCl3) (Halpern, 1973); D31 -514.8° (c = 0.3 in CHCl3) (Taniguchi).

Boiling point:

113°C/3mmHg(lit.)

Density 

1.329±0.06 g/cm3(Predicted)

refractive index 

nD25 1.5084

storage temp. 

Amber Vial, -20°C Freezer, Under Inert Atmosphere

solubility 

Chloroform (Sparingly), DMSO (Slightly), Ethyl Acetate (Slightly)

form 

liquid

color 

Colourless to Yellow

Merck 

14,5465

Stability:

Light Sensitive

InChI

InChI=1S/C6H6O3/c7-5-2-1-4-3-8-6(5)9-4/h1-2,4,6H,3H2/t4-,6+/m0/s1

InChIKey

HITOXZPZGPXYHY-UJURSFKZSA-N

SMILES

[C@@]12([H])O[C@@]([H])(OC1)C(=O)C=C2

LogP

-0.740 (est)

Safety Information

Risk Statements 

36

Safety Statements 

26

WGK Germany 

WGK 3

RTECS 

JG7020000

HS Code 

2932990090

Storage Class

10 - Combustible liquids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2

LEVOGLUCOSENONE Usage And Synthesis

Chemical Properties

Colourless to Yellow Oil

Uses

useful carbohydrate synthon

Uses

(-)-Form Levoglucosenone is a pyrolysis product of cellulose and cellulose-containing materials including pulp and paper waste products. Known as a pyrolytic product of cellulose, its very useful as a chiral source for synthesizing natural products.

Uses

Chiral building block in organic synthesis.

Definition

ChEBI: Levoglucosenone is an anhydrohexose and a deoxyketohexose.

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