Skip to Content
Merck
All Photos(1)

Documents

SMB00504

Sigma-Aldrich

Levoglucosenone

≥95% (GC)

Synonym(s):

(1S,5R)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one, 1,6-anhydro-3,4-dideoxyhex-3-enopyran-2-ulose, 6,8-Dioxabicyclo[3.2.1]oct-2-en-4-one

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C6H6O3
CAS Number:
37112-31-5
Molecular Weight:
126.11
MDL number:
MFCD00191664
UNSPSC Code:
12352201
PubChem Substance ID:
329825031
NACRES:
NA.25

Assay

≥95% (GC)

form

liquid

storage temp.

2-8°C

SMILES string

[H][C@]1(C=CC2=O)CO[C@]2([H])O1

InChI

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

InChI key

HITOXZPZGPXYHY-UJURSFKZSA-N

Looking for similar products? Visit Product Comparison Guide

General description

In the laboratory, levoglucosenone (1,6-anhydro-3,4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose, LGO) can be synthesized from H3PO4-treated, Kraft waste-paper via pyrolysis. It can also be synthesized from the acid-treated cellulose and paper via pyrolysis. It undergoes Michael-addition reaction with diethyl malonate, ethyl cyanoacetate, 2-nitropropane and 2-methylcyclohexanone in the presence of various catalysts to afford 4-substituted levoglucosenone derivatives having the D-erythro configuration. Magnetic super acid (SO4-2/TiO2-Fe3O4) mediated pyrolysis of cellulose and poplar wood has been proposed for the selective synthesis of LGO.

Application

Levoglucosenone may be used in the synthesis of the following:
  • various deoxy, keto and branched-chain sugars
  • 4-thio and 4-substituted sugar derivatives
  • natural stereoisomer of serricornin

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Some reactions of levoglucosenone.
Shafizadeh F, et al.
Carbohydrate Research, 71(1), 169-191 (1979)
A stereoselective synthesis of ?natural?(4S, 6S, 7S)-serricornin, the sex pheromone of cigarette bettle, from levoglucosenone.
Mori M, et al.
Tetrahedron Letters, 23(44), 4593-4596 (1982)
Michael-addition reactions of levoglucosenone.
Shafizadeh F, et al.
Carbohydrate Research, 102(1), 217-230 (1982)
Preparation of 1, 6-anhydro-3, 4-dideoxy-β-D-glycero-hex-3-enopyranos-2-ulose (levoglucosenone) and some derivatives thereof.
Shafizadeh F and Chin PPS.
Carbohydrate Research, 58(1), 79-87 (1977)
Qiang Lu et al.
Bioresource technology, 171, 10-15 (2014-09-01)
Magnetic superacid (SO4(2-)/TiO2-Fe3O4) was prepared for catalytic fast pyrolysis of cellulose and poplar wood to produce levoglucosenone (LGO). Its catalytic activity was evaluated via pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS) experiments, and compared with the non-magnetic SO4(2-)/TiO2, phosphoric acid (H3PO4) and sulfur

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service