87-79-6 , L-Sorbose ,
L-山梨糖,
cas: 87-79-6
C6H12O6 / 180.16
MFCD00151097
L-(–)-Sorbose is a monosaccharide and an intermediate in the biosynthesis of L-ascorbic acid in bacteria. It is formed via dehydrogenation of D-sorbitol by D-sorbitol dehydrogenase (SLDH). L-(–)-Sorbose has commonly been used as a starting material in the commercial biosynthesis of L-ascorbic acid.
Sorbose, also known as Keto-L-sorbose, is a ketose sugar that is commonly used in the commercial synthesis of ASCORBIC ACID. It is an enantiomer of a keto-D-sorbose. L-(–)-Sorbose is a monosaccharide and an intermediate in the biosynthesis of L-ascorbic acid in bacteria. It is used as a starting reagent for the commercial biosynthesis of ascorbic acid (vitamin C).
CAS Number | 87-79-6 |
Product Name | L-(-)-Sorbose |
IUPAC Name | (3S,4R,5S)-1,3,4,5,6-pentahydroxyhexan-2-one |
Molecular Formula | C6H12O6 |
Molecular Weight | 180.16 g/mol |
InChI | 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 |
InChI Key | BJHIKXHVCXFQLS-OTWZMJIISA-N |
SMILES | C(C(C(C(C(=O)CO)O)O)O)O |
Solubility | Soluble in DMSO |
Synonyms | Sorbose; Esorben; HSDB 780; Sorbin; Sorbinose; L-Sorbinose; L-Sorbose; NSC 97195; NSC-97195; NSC97195; |
Canonical SMILES | C(C(C(C(C(=O)CO)O)O)O)O |
Isomeric SMILES | C([C@@H]([C@H]([C@@H](C(=O)CO)O)O)O)O |
Title: Sorbose
CAS Registry Number: 87-79-6
CAS Name: L-Sorbose
Additional Names: sorbin; sorbinose
Molecular Formula: C6H12O6
Molecular Weight: 180.16
Percent Composition: C 40.00%, H 6.71%, O 53.28%
Literature References: From sorbitol by fermentation with Acetobacter suboxydans: Perlman, J. Chem. Educ. 36, 60 (1959); Lockwood, Methods Carbohydr. Chem. 1, 151 (Academic Press, New York, 1962).
Properties: Orthorhombic, bisphenoidal crystals. About as sweet as sucrose. d15 1.65. mp 165°. [a]D30 -42.7° (c = 5). pKa (17.5° ): 11.55. Freely sol in water; almost insol in alcohol. Reduces Fehling's soln.
Melting point: mp 165°
pKa: pKa (17.5° ): 11.55
Optical Rotation: [a]D30 -42.7° (c = 5)
Density: d15 1.65
Use: In the manuf 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).
CAS No: 87-79-6 Synonyms: (3S,4R,5S)-1,3,4,5,6-Pentahydroxyhexan-2-one MDL No: MFCD00151097 Chemical Formula: C6H12O6 Molecular Weight: 180.16 |
References: 1. Hotchkiss D, Soengas R, Simone MI, van Ameijde J, Hunter S, Cowley AR, Fleet GWJ, Tetrahydron Lett. 2004, 45, 9461-94642. Leang K, Maekawa K, Menavuvu BT, Morimoto K, Granström TB, Takada G, Izumori K, J. Biosci. Bioeng. 2004, 97, 383-388 |
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