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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

Quality Level

200

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

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK6391
BCCK7323
BCCL2098
BCCG6781
BCCF2591

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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
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 polynitrogenated analogues of glucopyranoses from levoglucosan
Bailliez V, et al.
Tetrahedron, 60(5), 1079-1085 (2004)
Practical synthesis of 1, 6-anhydro-2, 4-dideoxy-β -D-glycero-hexopyranos-3-ulose from levoglucosan
Belyk K, et al.
The Journal of Organic Chemistry, 65(8), 2588-2590 (2000)
The controlled synthesis of polyglucose in one-dimensional coordination nanochannels
Kobayashi Y, et al.
Chemical Communications (Cambridge, England), 52(29), 5156-5159 (2016)
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