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16-anhydro-b-D-Glucose

CAT: 0013-GTR19158374-01Size: 1 gDry Ice: NoHazardous: No
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Description
16-anhydro-b-D-Glucose (Levoglucosan) is an anhydrohexose that is the 16-anhydro-derivative of beta-D-glucopyranose. It is formed from the pyrolysis of carbohydrates such as starch and cellulose. Levoglucosan can also be utilized in the synthesis of chiral polymers such as unhydrolysable glucose polymers. Levoglucosan is also produced via caramelization of sugar. Consumption of caramel or caramel-containing sweets can lead to a short-term 5X increase in urinary levels of levoglucosan (from 20 uM/mM creatinine to 100 uM/mM creatinine) .
CAS Number
498-07-7
Product Name Alternative
Levoglucosan
Field of Research
Pharmacology & Drug Discovery
Purity
>98% (HPLC)
Solubility
DMSO:10 mM
Smiles
O[C@@H]1[C@H]2CO[C@H] (O2) [C@H] (O) [C@H]1O
Molecular Formula
C6H10O5
Molecular Weight
162.14
Storage Conditions
Storage temperature: -20°C. Stability: ≥ 2 years
Notes
For research use only.

Chemical Information

Levoglucosan

Levoglucosan is a anhydrohexose that is the 1,6-anhydro-derivative of beta-D-glucopyranose. It has a role as an Arabidopsis thaliana metabolite, a biomarker and a human metabolite.

CAS Number498-07-7
PubChem CID2724705
IUPAC Name(1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
Molecular FormulaC6H10O5
Molecular Weight162.14
XLogP-2.1
Topological Polar Surface Area79.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count0
Heavy Atom Count11
Formal Charge0
Complexity161
SMILES
C1[C@@H]2[C@H]([C@@H]([C@H]([C@H](O1)O2)O)O)O
InChI
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
InChIKey
TWNIBLMWSKIRAT-VFUOTHLCSA-N
Chemical Structure
2D Structure
2D structure of Levoglucosan
CAS: 498-07-7
CID: 2724705
Formula: C6H10O5
MW: 162.14
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight162.14
XLogP3-2.1
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count0
Exact Mass162.05282342
Monoisotopic Mass162.05282342
Topological Polar Surface Area79.2 Ų
Heavy Atom Count11
Formal Charge0
Complexity161
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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