Psicose

Psicose
Names
IUPAC name
D-ribo-Hex-2-ulose
Systematic IUPAC name
(3R,4R,5R)-1,3,4,5,6-Pentahydroxyhexan-2-one
Other names
D-Allulose; D-Psicose; D-Ribo-2-hexulose; Pseudofructose
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.182 Edit this at Wikidata
MeSH psicose
UNII
  • InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5-,6+/m1/s1 checkY
    Key: BJHIKXHVCXFQLS-PUFIMZNGSA-N checkY
  • InChI=1/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-9,11-12H,1-2H2/t3-,5-,6+/m1/s1
    Key: BJHIKXHVCXFQLS-PUFIMZNGBH
  • O=C([C@H](O)[C@H](O)[C@H](O)CO)CO
Properties
C6H12O6
Molar mass 180.156 g·mol−1
Melting point 58 °C (136 °F; 331 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

D-Psicose (C6H12O6), also known as D-allulose or simply allulose, is an epimer of fructose that is used by some commercial food and beverage manufacturers as a low-calorie sweetener.[2] Allulose occurs naturally in small quantities in a variety of foods. It was first identified in the 1940s, although the enzymes needed to produce it on an industrial scale were not discovered until the 1990s.

The U.S. Food and Drug Administration (FDA) has accepted a petition for generally recognized as safe (GRAS) for allulose as a sugar substitute in various specified food categories.[3][4] Because it is absorbed and metabolized differently from other sugars, the FDA has exempted allulose from the listing of total and added sugars on the Nutrition and Supplement Facts labels, but requires its weight listing as a carbohydrate, with 0.4 kcal/g (about 1/10 the calories of ordinary carbohydrates).[5]

Studies have shown the commercial product is not absorbed in the human body the way common sugars are and does not raise insulin levels, but more testing may be needed to evaluate any other potential side effects.[6] In 2020, the U.S. FDA accepted the conclusion by Samyang that the maximum tolerable consumption for a 60 kg adult was 33 to 36 grams per day.[7]

  1. ^ Lide, David R.; Milne, G.W.A., eds. (30 Dec 1993). CRC Handbook of Data on Organic Compounds (3rd ed.). CRC Press. p. 4596.
  2. ^ Hossain, Akram; Yamaguchi, Fuminori; Matsuo, Tatsuhiro; Tsukamoto, Ikuko; Toyoda, Yukiyasu; Ogawa, Masahiro; Nagata, Yasuo; Tokuda, Masaaki (November 2015). "Rare sugar d-allulose: Potential role and therapeutic monitoring in maintaining obesity and type 2 diabetes mellitus". Pharmacology & Therapeutics. 155: 49–59. doi:10.1016/j.pharmthera.2015.08.004. PMID 26297965.
  3. ^ "GRN No. 400". fda.gov. FDA. Retrieved 26 December 2019.
  4. ^ "GRN No. 498". FDA. Retrieved 19 December 2019.
  5. ^ "The Declaration of Allulose and Calories From Allulose on Nutrition and Supplement Facts Labels; Availability". Federal Register. 2020-10-19. Retrieved 2020-11-16.
  6. ^ Elejalde-Ruiz, Alexia (August 22, 2019). "A natural sweetener with a tenth of sugar's calories. Allulose, developed in Hoffman Estates, could be 'breakthrough ingredient.'". Chicago Tribune. Retrieved 2019-08-25.
  7. ^ Cite error: The named reference GRAS828 was invoked but never defined (see the help page).