Basic information
- CAS
498-07-7- Standard SMILES
O[C@@H]1[C@@H](O)[C@@H]2OC[C@@H](O2)[C@H]1O- InChIKey
TWNIBLMWSKIRAT-VFUOTHLCSA-N- Molecular formula
- C6H10O5
- Average molar mass
- 162.14 g/mol
- Monoisotopic mass
- 162.05282342
Names & identifiers
- Preferred name
- Levoglucosan
- IUPAC
- (1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol
- English name
- 1,6-Anhydro-beta-D-glucopyranose
- Molecular formula
- C6H10O5
- Molecular weight
- 162.14
Names & synonyms
Levoglucosan498-07-71,6-Anhydro-beta-D-glucopyranoseLeucoglucosan(1R,2S,3S,4R,5R)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol1,6-Anhydro-beta-glucopyranose5132N17FSDCHEBI:30997beta-D-Glucopyranose, 1,6-anhydro-NSC-46243DTXSID90904321(1R,2S,3S,4R,5R)-6,8-dioxabicyclo(3.2.1)octane-2,3,4-triol
Show more names
1,6-Anhydro-β-D-glucopyranose1,6-Anhydro-β-D-glucose1,6-ANHYDRO-B-D-GLUCOSEβ-D-Glucopyranose, 1,6-anhydro-1,6-Anhydro-
RefChem:153210DTXCID301474706207-855-01,6-Anhydro-beta-D-glucoseGlucosan1,6-Anhydroglucose1,6-Anhydro-b-D-glucopyranose1,6-Anhydro-D-glucose
Database identifiers
- CAS
498-07-7- PubChem CID
- 2724705
- ChEMBL
CHEMBL3138649- ChEBI
CHEBI:30997- UNII
- 5132N17FSD
- EC Number
- 207-855-0
- Nikkaji
- J12.571G
Properties
Computed structural properties
- XLogP
- -2.1
- Topological polar surface area
- 79.2 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 0
- Heavy atoms
- 11
- Formal charge
- 0
- Complexity
- 161
Experimental & physicochemical properties
Solubility62.3 mg/mL
Melting Point183 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 182 · 182-184 °C(lit.)
- alpha
- -66 · -66 º (C=1 IN H2O)
- Boiling point
- 208.81 °C · 208.81°C (rough estimate)
- Density
- 1.2132 · 1.2132 (rough estimate)
- refractive index
- -66.5 ° · -66.5 ° (C=2, H2O)
- storage temp.
- 2 · 2-8°C
- solubility
- Methanol (Slightly), Water (Sparingly)
- pka
- 13.4 · 13.40±0.60(Predicted)
- form
- Crystalline Powder or Crystals
- color
- White to slightly beige
- optical activity
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 75% (3 of 4) of all reports.
Warning
H312 (25%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H315 (25%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (25%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (25%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 4 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 3 of 4 reports by companies.；There is 1 notification provided by 1 of 4 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
.beta.-D-Glucopyranose, 1,6-anhydro-: Does not have an individual approval but may be used under an appropriate group standard
.beta.-D-Galactopyranose, 1,6-anhydro-: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and Categories
Acute Tox. 4 (25%)；Skin Irrit. 2 (25%)；Eye Irrit. 2 (25%)；STOT SE 3 (25%)
Acute Tox. 4 (25%)；Acute Tox. 4 (25%)；Skin Irrit. 2 (25%)；Eye Irrit. 2A (25%)；Acute Tox. 4 (25%)；STOT SE 3 (25%)
Regulatory information
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
Uses1,6-Anhydrohexopyranoses have proven to be valuable synthons for the preparation of biologically important and structurally diverse products (e.g. rifamycin S, indanomycin, thromboxane B2, (+)-biotin , tetrodotoxin, quinone, and macrolide antibiotics) as well as for modified sugars.
Uses1,6-Anhydro-beta-D-glucopyranose is used for the preparation of biologically important and structurally diverse products such as rifamycin S, indanomycin, thromboxane B2, (+)-biotin, tetrodotoxin, quinone, macrolide antibiotics and modified sugars. It is used as a chemical tracer for biomass burning in atmospheric chemistry studies, particularly with respect to airborne particulate matter. It aids in the production of bioethanol.
Uses1,6-Anhydro-β-D-glucose is an useful carbohydrate synthon pharmaceutical intermediate.
General Description1,6-Anhydro-β-D-glucose (Levoglucosa), belonging to the class of anhydrosugars, is an indicator of the burning of biomass in atmospheric aerosol, snow, and ice. It is formed via pyrolysis of glucans, such as cellulose and starch. Levoglucosa is also found in municipal waste and thermochemical processing products of biomass and soil.
Upstream & downstream products
Downstream products
Suppliers103 total
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Related reactions
3 records
Compound notes
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