levoglucosenone
6,8-dioxabicyclo(3.2.1)oct-2-en-4-one, (1S)-
Identification
| Name | levoglucosenone |
| IUPAC | (1S)-6,8-dioxabicyclo[3.2.1]oct-2-en-4-one |
| CAS Number | 37112-31-5 |
| FDA UNII | B7N23SN1LB |
| Molecular Formula | C6 H6 O3 |
| Molecular Weight | 126.11142000 |
| MDL Number | MFCD00191664 |
| Beilstein | 4859778 |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 254.40 °C. @ 760.00 mm Hg (est) |
| Flash Point | 209.00 °F. TCC ( 98.20 °C. ) (est) |
| logP (o/w) | -0.740 (est) |
| Soluble in | water, 1.431e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | information only not used for fragrances or flavors |
| Recommendation for levoglucosenone usage levels up to | not for fragrance use. |
| Recommendation for levoglucosenone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
1,6-
anhydro-3,4-dideoxyhex-3-enopyran-2-ulose
(1S)-6,8-
dioxabicyclo(3.2.1)oct-2-en-4-one
6,8-
dioxabicyclo(3.2.1)oct-2-en-4-one, (1S)-
PubMed:
Catalytic fast pyrolysis of cellulose and biomass to produce levoglucosenone using magnetic SO4(2-)/TiO2-Fe3O4.
PubMed:
Theoretical insight into the pyrolytic deformylation of levoglucosenone and isolevoglucosenone.
PubMed:
Total synthesis of (+)-chloriolide.
PubMed:
Synthesis of tri-O-acetyl-D-allal from levoglucosenone.
PubMed:
1,3-Dipolar cycloaddition reactions of azomethine ylides with a cellulose-derived chiral enone. A novel route for organocatalysts development.
PubMed:
Mechanism research on cellulose pyrolysis by Py-GC/MS and subsequent density functional theory studies.
PubMed:
Preparation of levoglucosenone through sulfuric acid promoted pyrolysis of bagasse at low temperature.
PubMed:
Catalytic fast pyrolysis of cellulose to prepare levoglucosenone using sulfated zirconia.
PubMed:
Cycloaddition and one-carbon homologation studies in the synthesis of advanced iridoid precursors.
PubMed:
Design, synthesis, and biological evaluation of levoglucosenone-derived ras activation inhibitors.
PubMed:
Pi-stacking effect on levoglucosenone derived internal chiral auxiliaries. A case of complete enantioselectivity inversion on the Diels-Alder reaction.
PubMed:
Quasienantiomeric levoglucosenone and isolevoglucosenone allow the parallel kinetic resolution of a racemic nitrone.
PubMed:
Inhibition of acid-catalyzed depolymerization of cellulose with boric acid in non-aqueous acidic media.
PubMed:
An efficient total synthesis of optically active tetrodotoxin from levoglucosenone.
PubMed:
[Unsaturated sugars in enantiospecific synthesis of natural low-molecular bioregulators and their structural analogues].
PubMed:
Microwave-assisted regioselective cycloaddition reactions between 9-substituted anthracenes and levoglucosenone.
PubMed:
The use of levoglucosenone and isolevoglucosenone as templates for the construction of C-linked disaccharides.
PubMed:
Highly diastereoselective Diels-Alder reaction using a chiral auxiliary derived from levoglucosenone.
PubMed:
[Effect of acid hydrolysis of oak wood on its aroma-forming complex].
PubMed:
Functionalized S-thio-di- and S-oligosaccharide precursors as templates for novel SLex/a mimetic antimetastatic agents.
PubMed:
Thio-sugars VII. Effect of 3-deoxy-4-S-(beta-D-gluco- and beta-D-galactopyranosyl)-4-thiodisaccharides and their sulfoxides and sulfones on the viability and growth of selected murine and human tumor cell lines.
PubMed:
Comparative Studies of Cathodically-Promoted and Base-Catalyzed Michael Addition Reactions of Levoglucosenone.
PubMed:
A Facile Entry into Naphthopyran Quinones via an Annelation Reaction of Levoglucosenone. The Total Synthesis of (-)-Hongconin(1).
PubMed:
Initiating activity of eight pyrolysates of carbohydrates in a two-stage mouse skin tumorigenesis model.
PubMed:
Chromosome aberrations induced by pyrolysates of carbohydrates in Chinese hamster V79 cells.
PubMed:
An unusual reaction of 1,6-anhydroaldohexopyranose derivatives leading to glycals.