| Identification | Back Directory | [Name]
D-PSICOSE | [CAS]
551-68-8 | [Synonyms]
C06468
D-PSICOSE
MAIZED-PSICOSE
D-Psicose ,98%
D-Pseudofructose
d-[UL-13C6]psicose
D-Erythro-hexulose
D-RIBO-2-KETOHEXOSE
D-Ribo-2-ketohexulose
(3R,4R,5R)-1,3,4,5,6-pentahydroxyhexan-2-one | [EINECS(EC#)]
208-999-7 | [Molecular Formula]
C6H12O6 | [MDL Number]
MFCD00083478 | [MOL File]
551-68-8.mol | [Molecular Weight]
180.16 |
| Chemical Properties | Back Directory | [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. ]
2-8°C
| [solubility ]
Methanol (Slightly, Heated, Sonicated), Water (Soluble, Sonicated) | [form ]
Powder | [pka]
11.86±0.20(Predicted) | [color ]
White | [Optical Rotation]
+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 |
| Hazard Information | Back Directory | [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 |
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