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

form 

Crystalline Powder or Crystals and Chunks

pka

pKa (17.5° ): 11.55

color 

White to off-white

Odor

Odorless

optical activity

[α]20/D 43±2°, c = 5% in H2O

Water Solubility 

354.8g/L(17 ºC)

Merck 

14,8726

BRN 

1724554

LogP

-1.029 (est)

CAS DataBase Reference

87-79-6(CAS DataBase Reference)

NIST Chemistry Reference

L-Sorbose(87-79-6)

EPA Substance Registry System

L-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

HS Code 

29400090

Hazardous Substances Data

87-79-6(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

L-(-)-SORBOSE Usage And Synthesis

Chemical Properties

White to off-white crystalline powder or crystals

Uses

L-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.

Uses

L-Sorbose is used as a starting reagent for the commercial biosynthesis of ascorbic acid (vitamin C).

Uses

In 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).

Definition

ChEBI: Keto-L-sorbose is a L-sorbose. It is an enantiomer of a keto-D-sorbose.

Biochem/physiol Actions

The L enatiomer of sorbose, a ketohexose monosaccharide.

Synthesis

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(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