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L-(-)-SORBOSE

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L-(-)-SORBOSE Basic information
Product Name:L-(-)-SORBOSE
Synonyms:L-SOR;L-(-)-SORBOSE;L-SORBOSE;SORBIN;SORBOSE;SORBOSE(L-);Esorben;Hex-2-ulose
CAS:87-79-6
MF:C6H12O6
MW:180.16
EINECS:201-771-8
Product Categories:FEED ADDITIVES;Dextrins、Sugar & Carbohydrates;Inhibitors;Biochemicals and Reagents;Carbohydrate Synthesis;Carbohydrates;Monosaccharides;MonosaccharideSpecialty Synthesis;Basic Sugars (Mono & Oligosaccharides);Biochemistry;Sorbose;Sugars
Mol File:87-79-6.mol
L-(-)-SORBOSE Structure
L-(-)-SORBOSE Chemical Properties
Melting point 163-165 °C
alpha -43 º (C=5% IN H2O)
Boiling point 232.96°C (rough estimate)
density 1.65 g/cm
refractive index -43 ° (C=1, H2O)
storage temp. Inert atmosphere,2-8°C
solubility H2O: 0.1 g/mL, clear, colorless to very faintly yellow
pkapKa (17.5° ): 11.55
form Crystalline Powder or Crystals and Chunks
color White to off-white
OdorOdorless
Optical Rotation[α]20/D 43±2°, c = 5% in H2O
Water Solubility 354.8g/L(17 ºC)
Merck 14,8726
BRN 1724554
InChI1S/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
InChIKeyBJHIKXHVCXFQLS-OTWZMJIISA-N
SMILESOC[C@H](O)[C@@H](O)[C@H](O)C(=O)CO
LogP-1.029 (est)
CAS DataBase Reference87-79-6(CAS DataBase Reference)
NIST Chemistry ReferenceL-Sorbose(87-79-6)
EPA Substance Registry SystemL-Sorbose (87-79-6)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 24/25-36-26-22
WGK Germany 3
RTECS WG3195025
TSCA TSCA listed
HS Code 29400090
Storage Class11 - Combustible Solids
Hazardous Substances Data87-79-6(Hazardous Substances Data)
MSDS Information
ProviderLanguage
SigmaAldrich English
ACROS English
L-(-)-SORBOSE Usage And Synthesis
Chemical PropertiesWhite to off-white crystalline powder or crystals
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).
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).
DefinitionChEBI: Keto-L-sorbose is a L-sorbose. It is an enantiomer of a keto-D-sorbose.
Biochem/physiol ActionsThe L enatiomer of sorbose, a ketohexose monosaccharide.
Synthesis
D(-)-Fructose

57-48-7

2-Hydroxypropanoic acid

849585-22-4

D-HAMAMELOSE

4573-78-8

L-(-)-SORBOSE

87-79-6

D-tagatose

87-81-0

D-PSICOSE

551-68-8

1,3-Dihydroxyacetone

96-26-4

DL-GLYCERALDEHYDE

56-82-6

The target compounds were synthesized from D-fructose by the following steps: 2-hydroxypropanoic acid, D-witch hazel sugar, (3S,4R,5S)-1,3,4,5,6-pentahydroxyhexan-2-one, (3S,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one, (3R,4R,5R)-1,3,4,5,6-pentahydroxyhexan-2-one, 1 ,3-dihydroxyacetone and DL-glyceraldehyde. This was done as follows: the D-fructose was reacted with MoO3 in water at 100 °C for 4 h. After completion of the reaction, the fructose-containing grades were separated by appropriate methods. Analysis using 1H NMR spectroscopy (shown in Fig. 8) confirmed the presence of sorbose in the separated grades.

References[1] Patent: US2017/15614, 2017, A1. Location in patent: Page/Page column 2; 13-14
Tag:L-(-)-SORBOSE(87-79-6) Related Product Information
L-(-)-SORBOSE Diacetone L-sorbose 2-KETO-L-GULONIC ACID 5-KETO-D-GLUCONIC ACID CALCIUM SALT 5-Keto-D-gluconic acid D-(+)-SORBOSE,D-SORBOSE,D-(+)-SORBOSE,D-SORBOSE 5-KETO-D-GLUCONIC ACID POTASSIUM SALT L-SORBOSE-1-PHOSPHATE POTASSIUM SALT,L-SORBOSE-1-PHOSPHATE POTASSIUM SALT L-[4-13C]SORBOSE,L-[4-13C]SORBOSE L-Sorbose, bis-O-(1-methylethylidene)-,L-Sorbose, bis-O-(1-methylethylidene)- 2,3-O-ISOPROPYLIDENE-1,6-DITOSYL-L-SORBOSE,2,3-O-ISOPROPYLIDENE-1,6-DITOSYL-L-SORBOSE C-7 SORBIN, PORCINE,SORBIN C-TERMINAL PEPTIDE AMIDE C-7 L-[6-13C]SORBOSE,L-[6-13C]SORBOSE C-20 SORBIN, PORCINE 3,4-DI-O-ACETYL-1,2-O-ISOPROPYLIDENE-5-O-TOSYL-A-L-SORBOSE,3,4-DI-O-ACETYL-1,2-O-ISOPROPYLIDENE-5-O-TOSYL-A-L-SORBOSE L-[5-13C]SORBOSE,L-[5-13C]SORBOSE sorbose-1-phosphate,sorbose-1-phosphate L-sorbose-1-phosphate reductase,L-sorbose-1-phosphate reductase

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