Xanthopterin

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Structural formula
Structure of xanthopterin
General
Surname Xanthopterin
other names
  • 2-amino-3 H , 5 H -pteridine-4,6-dione
  • 2-amino-1,5-dihydro-4,6-pteridinedione
Molecular formula C 6 H 5 N 5 O 2
Brief description

orange-yellow crystals

External identifiers / databases
CAS number
  • 119-44-8
  • 5979-01-1 (monohydrate)
EC number 204-325-0
ECHA InfoCard 100.003.932
PubChem 8397
Wikidata Q415862
properties
Molar mass 179.1362 g · mol -1
Physical state

firmly

Melting point

> 360 ° C (decomposition)

solubility
safety instructions
GHS hazard labeling
no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Xanthopterin is a heterocyclic compound that is derived from pterin . It occurs as a yellow pterin pigment z. B. in butterfly wings, from which Frederick Gowland Hopkins extracted such dyes for the first time in 1889 . Heinrich Otto Wieland and Clemens Schöpf isolated xanthopterin in its pure form from the wings of the lemon moth in 1924 . The structure of xanthopterin was only clarified in 1940 by Robert Purrmann .

Xanthopterin is also common in other insects and organisms; so it is found in wasps and in human urine. Various microorganisms can produce folic acid from xanthopterin .

See also: Phototrophy # Phototrophic Opisthokonta , paragraph: Phototrophy with Xanthopterin

properties

A crystal structure analysis of xanthopterin is not yet available because of the difficulty in growing suitable crystals. In contrast, xanthopterin hydrochloride could be examined by X-ray: it shows the depicted 4,6-dioxo structure, with protonation taking place at N (3).

Xanthopterin is relatively easily oxidized, with oxygenation at C-7 producing leucopterin .

Syntheses

Purrmann obtained xanthopterin from 2,4,5-triamino-6-hydroxypyrimidine and dichloroacetic acid in two synthesis steps, Koschara in one step with glyoxylic acid .

Individual evidence

  1. ↑ a b c d e entry on xanthopterin. In: Römpp Online . Georg Thieme Verlag, accessed on May 29, 2014.
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ Frederick Gowland Hopkins: Note on a yellow pigment in butterflies. In: Proc. Chem. Soc. , Vol. 5 (1889), p. 117, ISSN  0269-3135 .
  4. ↑ Heinrich Otto Wieland, Clemens Schöpf, in: Ber. German Chem. Ges. , Jg. 58 (1925), p. 2178, ISSN  0365-9488 .
  5. ↑ Robert Purrmann: About the wing pigments of butterflies. VII. Synthesis of Leucopterin and Nature of Guanopterin . In: Liebig's annals . tape 544 , 1940, ISSN  0075-4617 , pp. 182-190 , doi : 10.1002 / jlac.19405440111 .
  6. ↑ Jost H. Bieri et al. a .: Helv. Chim. Acta , Vol. 59 (1976), No. 7, pp. 2374-2379, ISSN  0018-019X .
  7. ↑ Robert Purrmann: The synthesis of Xanthopterin. About the wing pigments of the butterflies. X³ . In: Liebig's annals . tape 546 , no. 1-2 , 1941, ISSN  0075-4617 , pp. 98 , doi : 10.1002 / jlac.19415460107 .
  8. ^ Walter Koschara: Hoppe-Seylers Zeitschrift für Physiologische Chemie , Vol. 277 (1943), p. 159, ISSN  0018-4888 .