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316555

Sigma-Aldrich

1,6-Anhydro-β-D-glucose

99%

Synonym(s):

Levoglucosan

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About This Item

Empirical Formula (Hill Notation):
C6H10O5
CAS Number:
498-07-7
Molecular Weight:
162.14
Beilstein:
80998
EC Number:
207-855-0
MDL number:
MFCD00063248
UNSPSC Code:
12352201
PubChem Substance ID:
24859027
NACRES:
NA.22

Assay

99%

form

powder or crystals

optical activity

[α]18/D −66°, c = 1 in H2O

color

beige

mp

182-184 °C (lit.)

solubility

water: 50 mg/mL, clear, colorless

SMILES string

O[C@H]1[C@H](O)[C@H]2CO[C@H](O2)[C@@H]1O

InChI

1S/C6H10O5/c7-3-2-1-10-6(11-2)5(9)4(3)8/h2-9H,1H2/t2-,3-,4+,5-,6-/m1/s1

InChI key

TWNIBLMWSKIRAT-VFUOTHLCSA-N

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Application

1,6-Anhydro-β-D-glucose (Levoglucosan) can be used as a precursor for the synthesis of:
  • 1,6-anhydro-2,4-dideoxy-β-D-glycerohexopyranos-3-ulose.
  • Quasi-linear polyglucose (PGlc) via cationic ring-opening polymerization.
  • Polynitrogenated analogs of glucopyranoses.
  • 3-deoxy-3-fluorogalactopyranose and acetylated 4-deoxy-4-fluorogalactopyranose.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Bret A Schichtel et al.
Environmental science & technology, 51(17), 9846-9855 (2017-08-02)
Carbonaceous compounds are a significant component of fine particulate matter and haze in national parks and wilderness areas where visibility is protected, i.e., class I areas (CIAs). The Regional Haze Rule set the goal of returning visibility in CIAs on
Synthesis of polynitrogenated analogues of glucopyranoses from levoglucosan
Bailliez V, et al.
Tetrahedron, 60(5), 1079-1085 (2004)
Jackson Tham et al.
Environmental pollution (Barking, Essex : 1987), 248, 496-505 (2019-03-05)
This study characterizes impacts of peat-forest (PF) smoke on an urban environment through carbonaceous profiles of >260 daily PM2.5 samples collected during 2012, 2013 and 2015. Organic carbon (OC) and elemental carbon (EC) comprising eight carbonaceous fractions are examined for
Synthesis of Protected 3-Deoxy-3-fluoro-and 4-Deoxy-4-fluoro-d-galactopyranosides from Levoglucosan
Laine D, et al.
The Journal of Organic Chemistry, 82(9), 4986-4992 (2017)
Dimitra Balla et al.
Environmental science and pollution research international, 25(13), 12191-12205 (2017-09-10)
Two classes of polar organic compounds, dicarboxylic acids (DCAs) and sugars/sugar anhydrides (S/SAs), were measured in airborne particulate matter in the area of Thessaloniki, northern Greece. The target compounds were measured simultaneously in two particle fractions PM10 and PM2.5 during
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