D-PSICOSE Chemical Properties

Melting point:

109 °C

alpha 

D25 +4.7° (c = 4.3 in water; no detectable mutarotation)

Boiling point:

551.7±50.0 °C(Predicted)

Density 

1.589±0.06 g/cm3(Predicted)

refractive index 

16.3 ° (C=0.94, H2O)

storage temp. 

Sealed in dry,2-8°C

solubility 

Methanol (Slightly, Heated, Sonicated), Water (Soluble, Sonicated)

form 

Powder

pka

11.86±0.20(Predicted)

color 

White

optical activity

+4.7

Merck 

14,7924

InChI

InChI=1S/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4?,5+,6+/m1/s1

InChIKey

RFSUNEUAIZKAJO-NQAPHZHOSA-N

SMILES

[C@@H]1(O)[C@](O)(CO)O[C@H](CO)C1O

LogP

-1.029 (est)

CAS DataBase Reference

551-68-8

Safety Information

WGK Germany 

3

HS Code 

29400090

MSDS

• Language:English Provider:SigmaAldrich

D-PSICOSE Usage And Synthesis

Chemical Properties

Clear colorless to yellow liquid or powder

Uses

D-Psicose is a C3 epimer of L-Fructose, which maintains the ability to reduce fat accumulation when added to a diet through inhibition of intestinal α-glucosidase.

Definition

ChEBI: The D-enantiomer of psicose.

Synthesis

General procedure for the synthesis of D-fructose from D-anhydrous glucose: 40 mL of deionized water, 4 g of ternary metal-based hydrotalcite complex catalyst with a molar ratio of Mg:Al:Sn = 3:1:1 were added to a 100 mL three-necked flask, followed by the addition of 10 g of D-glucose anhydrous, and stirred until complete dissolution. The reaction system was placed in a constant temperature water bath and reacted at 90 °C for 3 h under N2 protection. At the end of the reaction, the reaction mixture was concentrated and separated and purified by column chromatography to finally obtain the target product D-fructose in 29.7% yield.

Enzyme inhibitor

This ketohexose (FW = 180.16 g/mol), also known as D-ribo-2-hexulose and reportedly fpound in cane molasses, has epimers of D-psicose are Dfructose, D-sorbose, and L-tagatose. D-Psicose is an alternative substrate for fructokinase. The structural composition of D-psicose at 27°C in D2O is 22% a-pyranose, 24% b-pyranose, 39% a-furanose, and 15% bfuranose. Target(s): ketohexokinase, or hepatic fructokinase; also alternative substrate.

References

[1] Patent: CN104262416, 2016, B. Location in patent: Paragraph 0043; 0044
[2] ACS Catalysis, 2013, vol. 3, # 7, p. 1469 - 1476
[3] Green Chemistry, 2013, vol. 15, # 10, p. 2777 - 2785

D-PSICOSE(551-68-8)Related Product Information

• Cyclohexane-1,2,3,4,5,6-hexol
• D-tagatose
• Phosphatidylserine
• D-Galactose
• 2-Deoxy-D-ribose
• Boron carbide
• Sucralose
• Xylitol
• 1,2:5,6-Di-O-isopropylidene-α-D-allofuranose
• psicose
• D-TALOSE
• PSICOSE
• L-LYXOSE
• D-PSICOSE
• L-Psicose
• METHYL 2-KETO-L-GULONATE
• PSICOSE DIACETONIDE
• 3-ACETYL-1,2-O-ISOPROPYLIDENE-6-O-TRITYL-B-L-ARABINO-HEXOFURANOS-5-ULOSE