Psicose

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Psicose
Names
IUPAC name
(3R,4R,5R)-1,3,4,5,6-Pentahydroxyhexan-2-one
Other names
D-Psicose; D-Allulose; D-Ribo-2-hexulose
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.008.182 Edit this at Wikidata
MeSH psicose
  • 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 (D-allulose, D-ribo-2-hexulose, C6H12O6) is a low-energy monosaccharide sugar present in small quantities in natural products. First identified in wheat more than 70 years ago, psicose is a C-3 epimer of D-fructose, and is present in small quantities in agricultural products and commercially prepared carbohydrate complexes. The sweetness of psicose is estimated to be 70% of the sweetness of sucrose.[2] As of 2018, major commercial food or beverage manufacturers use psicose as a sweetener.

History

The first mass-production method for psicose was established when Ken Izumori at Kagawa University in Japan discovered the key enzyme, D-tagatose 3-epimerase, to convert fructose to D-psicose in 1994.[3][4] This method of production has a high yield, but suffers from a very high production cost.

The U.S. Food and Drug Administration (FDA) lists psicose as generally recognized as safe (GRAS).[5] Psicose is not approved for use in the European Union. CJ CheilJedang was the first company to file for GRAS status in the US.[6]

Commercial application

Commercial manufacturers and food laboratories are looking into properties of D-psicose that may differentiate it from sucrose and fructose sweeteners, including an ability to induce the high foaming property of egg white protein and the production of antioxidant substances produced through the Maillard reaction.[7]

Commercial uses of psicose include low-calorie sweeteners in beverages, yogurt, ice cream, baked goods, and other typically high-calorie items. London-based Tate & Lyle released its proprietary variant of psicose, known as Dolcia Prima allulose,[8] and U.S.-based Anderson Global Group released its own proprietary variant into the North American market in 2015.[9][10]

Coca-Cola Company utilizes psicose in Fuze low calorie Meyer Lemon Black Tea.

References

  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. ^ Chung, Min-Yu; Oh, Deok-Kun; Lee, Ki Won (1 Feb 2012). "Hypoglycemic health benefits of D-psicose". J Agric Food Chem. 60 (4). ACS: 863–869. doi:10.1021/jf204050w. PMID 22224918.
  3. ^ Itoh, Hiromichi; Okaya, Hiroaki; Khan, Anisur Rahman; et al. (1994). "Purification and characterization of D-tagatose 3-epimerase from Pseudomonas sp. ST-24". Biosci Biotechnol Biochem. 58: 2168–2171. doi:10.1271/bbb.58.2168. Archived from the original on 2012-08-04. {{cite journal}}: Unknown parameter |dead-url= ignored (|url-status= suggested) (help)CS1 maint: extra punctuation (link) CS1 maint: multiple names: authors list (link)
  4. ^ Itoh, Hiromichi; Sato, Tomoko; Izumori, Ken (1995). "Preparation of D-psicose from D-fructose by immobilized D-tagatose 3-epimerase". J Fermentation and Bioengineering. 80 (1). Elsevier B.V.: 101–103. doi:10.1016/0922-338X(95)98186-O.
  5. ^ "U.S. FDA. Agency Response Letter GRAS Notice No. GRN 000400". FDA. Retrieved 12 July 2015.
  6. ^ "GRAS Notice" (PDF). fda.gov. FDA. Retrieved 12 July 2015.
  7. ^ Daniells, Stephan (9 June 2008). "Rare sugar may replace sucrose for bakery and beyond". Food Navigator. Retrieved 12 July 2015.
  8. ^ Watson, Elaine (25 Feb 2015). "Tate & Lyle unveils Dolcia Prima allulose low-calorie-sugar: 'We believe this will change the food and beverage landscape forever'". foodnavigator-usa.com. William Reed Business Media SAS.
  9. ^ Gelski, Jeff (30 June 2015). "New low-calorie sweetener to launch at I.F.T." Food Business News. Retrieved 12 July 2015.
  10. ^ "AllSweet". Anderson Global Group.
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