Psicosis

from Wikipedia, the free encyclopedia
Structural formula
Structure of psicosis
Fischer projection , open-chain representation
General
Surname D - (+) - psicose, L - (-) - psicose
other names
  • (3 R , 4 R , 5 R ) -1,3,4,5,6-pentahydroxy-2-hexanone
  • (3 S , 4 S , 5 S ) -1,3,4,5,6-pentahydroxy-2-hexanone
  • Allulose
Molecular formula C 6 H 12 O 6
Brief description

white solid

External identifiers / databases
CAS number
  • 23140-52-5 ( DL -Psicose)
  • 551-68-8 ( D- Psicose)
  • 16354-64-6 ( L -Psicose)
PubChem 90008
Wikidata Q423198
properties
Molar mass 180.16 g mol −1
Physical state

firmly

Melting point
  • 96-102 ° C (D-psicose)
  • 113 ° C (L-psicosis)
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Psicose (also allulose ) is a monosaccharide from the group of ketohexoses . It is to be marketed as a low-calorie sugar substitute under the name Allulose.

Occurrence

D -Psicose occurs only very rarely in nature and only in small amounts. It is only metabolized to a small extent by humans and therefore provides only a fraction of the energy that an equal amount of D- glucose would provide.

As with any sugar (except for dihydroxyacetone) there are two enantiomeric forms that behave like an image and a mirror image. L -Psicose does not occur in nature and, as an enantiomer of natural D -Psicose, is only of academic importance.

properties

An intramolecular ring closure occurs in aqueous solution, so that an equilibrium is established between the keto form and the two ring forms (approximately equal parts α / β- furanose and α / β- pyranose form).

D -Psicose - spellings
Wedge formula Haworth notation
D-Psicose Keilstrich.svg Alpha-D-Psicofuranose.svg
α- D -psicofuranose
Beta-D-Psicofuranose.svg
β- D -psicofuranose
Alpha-D-Psicopyranose.svg
α- D -psicopyranose
Beta-D-Psicopyranose.svg
β- D -psicopyranose

use

Studies have shown that allulose is not absorbed in the human body in the same way as ordinary sugar and does not increase insulin levels. Allulose has 0.2 calories per gram, while fructose has four calories per gram.

Allulose was first discovered in the 1940s. The first mass production method for allulose was developed in Japan in 1994 when the key enzyme D -tagatose-3-epimerase was discovered, which converts fructose to allulose. This production method has proven to be complex and very expensive.

In 2012, allulose was declared a safe sugar substitute by the US Food and Drug Administration (FDA) in several specified food categories. Allulose is not yet approved in the EU; The company Savanna Ingredients GmbH , which belongs to the Cologne sugar manufacturer Pfeifer & Langen , is developing a process for the production of sugar beet and is planning to be approved for marketing by 2021 in 2018.

Web links

Commons : Psicose  - collection of images, videos and audio files

Individual evidence

  1. a b Product information from Cosmo Bio Co. LTD (Tokyo) (PDF file; 46 kB) . April 3, 2007.
  2. a b Entry on L-Psicose at TCI Europe, accessed on June 25, 2011.
  3. a b D-Psicose data sheet from Sigma-Aldrich , accessed on June 16, 2011 ( PDF ).
  4. ^ Alfred D. French, Michael K. Dowd: Analysis of the ring-form tautomers of psicose with MM3 (92)] , in: Journal of Computational Chemistry , 1994 , 15  (5), pp. 561-570; doi : 10.1002 / jcc.540150508 .
  5. Hiromichi Itoh, Hiroaki Okaya, Anisur Rahman Khan, Shigeyuki Tajima, Shigeru Hayakawa, Ken Izumori: Purification and characterization of D-tagatose 3-epimerase from Pseudomonas sp. ST-24 . In: Biosci Biotechnol Biochem . 58, 1994, pp. 2168-2171. doi : 10.1271 / bbb.58.2168 .
  6. Hiromichi Itoh, Tomoko Sato, Ken Izumori: Preparation of D-psicose from D-fructose by immobilized D-tagatose 3-epimerase . In: Elsevier BV (Ed.): J Fermentation and Bioengineering . 80, No. 1, 1995, pp. 101-103. doi : 10.1016 / 0922-338X (95) 98186-O .
  7. Aachener Nachrichten: Elsdorf-based company wants to produce sugar without calories , July 2, 2018, accessed on January 28, 2020