L-(-)-Sorbose
Basic information
- CAS
87-79-6- Standard SMILES
O=C(CO)[C@@H](O)[C@H](O)[C@@H](O)CO- InChIKey
BJHIKXHVCXFQLS-OTWZMJIISA-N- Molecular formula
- C6H12O6
- Average molar mass
- 180.16 g/mol
- Monoisotopic mass
- 180.0633881
Overview
Keto-L-sorbose is a L-sorbose. It is an enantiomer of a keto-D-sorbose.
Names & identifiers
- Preferred name
- L-(-)-Sorbose
- IUPAC
- (3S,4R,5S)-1,3,4,5,6-pentahydroxyhexan-2-one
- English name
- L-(-)-Sorbose
- Molecular formula
- C6H12O6
- Molecular weight
- 180.16
Names & synonyms
L-(-)-Sorbose87-79-6(3S,4R,5S)-1,3,4,5,6-pentahydroxyhexan-2-oneDTXSID1048704DTXCID8028630GlyTouCan:G96062UJRefChem:1048327G96062UJSorbinSorbinoseketo-L-sorboseL-Sorbinose
Show more names
L-SORBOSESORBOSEHex-2-uloseL-SORL-SorinEsorbenL-Sorbinl-sorbosFoic acid
L-xylo-2-HexuloseMFCD00151097L(-)-SorboseUNII-NV2001607YSORBOSE [MI]L-1,3,4,5,6-Pentahydroxyhexan-2-oneCHEBI:13172NV2001607Y
Database identifiers
- CAS
87-79-6- PubChem CID
- 6904
- DTXSID
DTXSID1048704- ChEMBL
CHEMBL1615232- ChEBI
CHEBI:13172- UNII
- NV2001607Y
- Nikkaji
- J4.280C
Properties
Computed structural properties
- XLogP
- -3.2
- Topological polar surface area
- 118 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 5
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 147
Physicochemical properties
- Melting point
- 163 · 163-165 °C
- alpha
- -43 · -43 º (C=5% IN H2O)
- Boiling point
- 232.96 °C · 232.96°C (rough estimate)
- Density
- 1.65 g/cm · 1.65 g/cm
- refractive index
- -43 ° · -43 ° (C=1, H2O)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 2 O: · H2O: 0.1 g/mL, clear, colorless to very faintly yellow
- form
- Crystalline Powder or Crystals and Chunks
- pka
- pKa (17.5° ): 11.55
- color
- White to off-white
- Odor
- Odorless
- optical activity
- 20 · [α]20/D 43±2°, c = 5% in H2O
- Water Solubility
- 354.8 g/L · 354.8g/L(17 ºC)
- Merck
- 14 · 14,8726
- BRN
- 1724554 · 1724554
- InChI
- 1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5+,6+/m0/s1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- WG3195025
- hs_code
- 29400090
- risk_code
- 36/37/38
- hazard_code
- Xi
- safety_code
- 24/25-36-26-22
- Storage Class
- 11 - Combustible Solids
- Hazardous Substances Data
- 87-79-6(Hazardous Substances Data)
Chemistry & industry
Applications
UsesL-Sorbose is a low molecular weight naturally occurring monosaccharide carbohydrate molecule. It has sweetness that is nearly equivalent to that of sucrose. This is a labeled analog.
UsesL-Sorbose is used as a starting reagent for the commercial biosynthesis of ascorbic acid (vitamin C).
UsesIn the manufacture of vitamin C (accounts for nearly 1000 tons of ascorbic acid produced every year). For conversion of L-sorbose to 2-keto-L-gulonic acid see Reichstein, Grüssner, Helv. Chim. Acta 17, 311 (1934).
Upstream & downstream products
Upstream raw materials
Downstream products
Additional notes
Related reactions
55 records
Compound notes
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