β-cryptoxanthin

from Wikipedia, the free encyclopedia
Structural formula
Structural formula of β-cryptoxanthin
General
Surname β-cryptoxanthin
other names
  • Caricaxanthin
  • Hydroxy-β-carotene
  • (3 R ) -β, β-caroten-3-ol
  • Cryptoxanthol
Molecular formula C 40 H 56 O
Brief description

red solid

External identifiers / databases
CAS number 472-70-8
PubChem 5281235
Wikidata Q392062
properties
Molar mass 552.87 g mol −1
Physical state

firmly

Melting point
  • 169-170 ° C
  • 158–159 ° C (racemates)
solubility
  • practically insoluble in water
  • slightly soluble in methanol, ethanol and petroleum ether
  • easily soluble in trichloromethane and fats
  • sparingly soluble in chloroform
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 .

β-Cryptoxanthin is a chemical compound from the group of carotenoids with a closed β- ionone ring.

With cryptoxanthin, a distinction is made between α- and β-cryptoxanthin, depending on whether it can be derived from α- or β-carotene by introducing a hydroxyl group into an ionone ring. β-Cryptoxanthin is a provitamin A , but only one molecule of vitamin A can be formed per molecule of β-cryptoxanthin.

Occurrence

orange

Both cryptoxanthines are found in oranges, which probably contain the greatest variety of carotenoids of all foods ( α- , β-carotene, lutein , α- , β-cryptoxanthin, violaxanthin and many others). Cryptoxanthines are also found in papaya , carrots , peppers , mandarins , wheat germ oil , physalis , in pumpkin and other fruits, in butter and in egg yolks . They are contained as a yellow pigment in the flower of the sunflower (Helianthus annuus). In addition to lutein and zeaxanthin, α- and β-cryptoxanthin are found in the form of esters in human skin. It is also detectable in both human and primate blood plasma, with concentrations lower than β-carotene and lutein. The concentration is usually higher in women than in men. The half-life in human blood is less than 12 days.

properties

β-Cryptoxanthin is a red solid that is practically insoluble in water.

use

Together with zinc, β-cryptoxanthin is said to have a preventive effect against rheumatoid arthritis . Despite being harmless, it is not approved as a food coloring. There is evidence of cancer preventive effects in lung cancer.

Individual evidence

  1. a b c d e f g Gerhard Eisenbrand, Peter Schreier: RÖMPP Lexikon Lebensmittelchemie, 2nd edition, 2006 . Georg Thieme Verlag, 2014, ISBN 3-13-179282-5 , p. 231 ( limited preview in Google Book search).
  2. a b c d e f data sheet β-cryptoxanthin, ≥97% (TLC) from Sigma-Aldrich , accessed on March 4, 2018 ( PDF ).
  3. a b c Robert Ebermann, Ibrahim Elmadfa: Textbook food chemistry and nutrition . Springer-Verlag, 2011, ISBN 978-3-7091-0211-4 , pp. 221 ( limited preview in Google Book search).
  4. External identifiers or database links for α-cryptoxanthin : CAS number: 24480-38-4, PubChem : 5281234 , ChemSpider : 4444646 , Wikidata : Q27133768 .
  5. ^ A b IARC Working Group on the Evaluation of Cancer-preventive Agents, World Health Organization, International Agency for Research on Cancer: Carotenoids . IARC, 1998, ISBN 978-92-832-3002-1 , pp. 46 ( limited preview in Google Book search).
  6. ^ Siegfried Knasmüller: Cancer and nutrition risks and prevention - scientific principles and nutrition recommendations . Georg Thieme Verlag, 2014, ISBN 978-3-13-170581-5 , p. 260 ( limited preview in Google Book Search).
  7. Hartmut Bertz, Gudrun Zürcher: Nutrition in Oncology Basics and Clinical Practice . Schattauer Verlag, 2014, ISBN 978-3-7945-2804-2 , p. 118 ( limited preview in Google Book search).