L-(-)-Sorbose

HCID 6904CAS 87-79-6

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Basic information

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

87-79-6L-(-)-Sorbose(3S,4R,5S)-1,3,4,5,6-pentahydroxyhexan-2-oneDTXSID1048704DTXCID8028630GlyTouCan:G96062UJRefChem:1048327G96062UJSorbinoseSorbinketo-L-sorboseMFCD00151097

Show more names

L-SORBOSESORBOSEHex-2-uloseL-SORL-SorinEsorbenL-Sorbinl-sorbosFoic acid

L(-)-SorboseL-SorbinoseUNII-NV2001607YSORBOSE [MI]L-xylo-2-HexuloseL-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 Å²
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
InChIKey: BJHIKXHVCXFQLS-OTWZMJIISA-N
SMILES: OC[C@H](O)[C@@H](O)[C@H](O)C(=O)CO
LogP: -1.029 · -1.029 (est)
CAS DataBase Reference: 87 · 87-79-6(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS): SORBOSE
EWG's Food Scores: 1 · 1
FDA UNII: 2001607 Y · NV2001607Y
NIST Chemistry Reference: L-Sorbose(87-79-6)
EPA Substance Registry System: L-Sorbose (87-79-6)
UNSPSC Code: 12352201 · 12352201
NACRES: 79 · NA.79
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 24 · 24/25-36-26-22
WGK Germany: 3 · 3
RTECS: 3195025 · WG3195025
TSCA: TSCA listed
HS Code: 29400090 · 29400090
Storage Class: 11 · 11 - Combustible Solids
Hazardous Substances Data: 87 · 87-79-6(Hazardous Substances Data)

Safety & regulation

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 · 3 items

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).