Skip to Content
Merck
All Photos(3)

Documents

Safety Information

923133

Sigma-Aldrich

Levoglucosenone

greener alternative

≥95%

Synonym(s):

(-)-Levoglucosenone, LGO, (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(3)

About This Item

Empirical Formula (Hill Notation):
C6H6O3
CAS Number:
37112-31-5
Molecular Weight:
126.11
MDL number:
MFCD00191664
UNSPSC Code:
12352201
NACRES:
NA.22

Quality Level

100

Assay

≥95%

form

liquid

greener alternative product characteristics

Safer Solvents and Auxiliaries
Use of Renewable Feedstocks
Learn more about the Principles of Green Chemistry.

sustainability

Greener Alternative Product

refractive index

n/D 1.50625

density

1.32 g/mL

greener alternative category

, Aligned

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

We are committed to bringing you greener alternative products, which adhere to one or more of The 12 Principles of Greener Chemistry. This product is biorenewable and thus aligns with ″Safer Solvents and Auxiliaries″ and ″Use of Renewable Feedstocks″. Click here for more information.
Levoglucosenone 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.

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

Other Notes

Levoglucosenone: A Chiral Platform Molecule Produced from Biomass

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

923133-VAR:
923133-BULK:
923133-100G:

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
MKCW8616
MKCW2070
MKCT8314
MKCQ6172

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

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

Visit the Document Library

Levoglucosenone and Its New Applications: Valorization of Cellulose Residues.
Comba M B, et al.
European Journal of Organic Chemistry, 590-604 (2018)
Jonas Kühlborn et al.
Natural product reports, 37(3), 380-424 (2019-10-19)
Covering: up to mid-2019 This review highlights the utilization of biomass-derived building blocks in the total synthesis of natural products. An overview over several renewable feedstock classes, namely wood/lignin, cellulose, chitin and chitosan, fats and oils, as well as terpenes
Recent Applications of Levoglucosenone as Chiral Synthon.
Sarotti A M, et al.
Current Organic Synthesis, 9(4), 439-459 (2012)

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