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Merck
CN

923133

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

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About This Item

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

Key Documents

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InChI

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

SMILES string

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

InChI key

HITOXZPZGPXYHY-UJURSFKZSA-N

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

functional group

ether, ketone

greener alternative category

, Aligned

storage temp.

2-8°C

Quality Level

100

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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

signalword

Warning

hcodes

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCW8616
MKCW2070
MKCT8314
MKCQ6172

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Recent Applications of Levoglucosenone as Chiral Synthon.
Sarotti A M, et al.
Current Organic Synthesis, 9(4), 439-459 (2012)
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

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