L-(-)-SORBOSE CAS 87-79-6

Introduction:Basic information about L-(-)-SORBOSE CAS 87-79-6, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

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 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)

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

57-48-7

849585-22-4

4573-78-8

87-79-6

87-81-0

551-68-8

96-26-4

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

L-(-)-SORBOSE Preparation Products And Raw materials

Raw materialsD-Sorbitol-->L-Tagatose-->L-(+)-THREOSE-->L-IDITOL-->L-GULOSE-->L-(-)-IDOSE-->D(-)-Fructose-->β-Hydroxypyruvic acid-->D-Serine-->L-Glyceraldehyde
Preparation Products2,2-DIMETHYL-4-PHENYL-1,3-DIOXOLANE-->L-xylo-hex-2-ulosonic acid-->2-Hydroxypropanoic acid-->D(-)-Fructose
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