Pterorhodin

Last updated
Pterorhodin
Pterorhodin.png
Names
IUPAC name
2-Amino-7-[(E)-(2-amino-4,6-dioxo-5,8-dihydro-3H-pteridin-7-ylidene)methyl]-3,5-dihydropteridine-4,6-dione
Identifiers
3D model (JSmol)
ChemSpider
MeSH pterorhodin
PubChem CID
  • InChI=1S/C13H10N10O4/c14-12-20-6-4(10(26)22-12)18-8(24)2(16-6)1-3-9(25)19-5-7(17-3)21-13(15)23-11(5)27/h1H,(H,18,24)(H,19,25)(H3,14,16,20,22,26)(H4,15,17,21,23,27)/b3-1+
    Key: STEFGLSLWLJVLH-HNQUOIGGSA-N
  • C(=C/1\C(=O)NC2=C(N1)N=C(NC2=O)N)\C3=NC4=C(C(=O)NC(=N4)N)NC3=O
Properties
C13H10N10O4
Molar mass 370.289 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pterorhodin is a pteridine pigment found in animals and plants. [1] It has been extracted in melanosomes of tree frogs, butterflies, and plants as a wine red pigment. [2] [3] In lemur tree frogs, pterorhodin allows skin to reflect the sun's heat. [4] [5] Pterorhodin gives pigment color to bristle worms [6] and is found in the iris of multiple bird species including the red-eyed vireo [7] and the common loon. [8]

References

  1. ↑ Ramakrishna Rao, K.; Meenakshisundaram, S.; Shanmugasundaram, E. R. B. (February 1967). "Formation and Identification of the Pigment Pterorhodin in a Mutant of Fusarium vasinfectum Atk". Nature. 213 (5075): 503–504. Bibcode:1967Natur.213..503R. doi:10.1038/213503a0. S2CID   4200675.
  2. ↑ Bagnara, Joseph T. (October 2003). "Enigmas of Pterorhodin, a Red Melanosomal Pigment of Tree Frogs". Pigment Cell Research. 16 (5): 510–516. doi:10.1034/j.1600-0749.2003.00075.x. PMID   12950730.
  3. ↑ Russell, Peter B.; Purrmann, Robert; Schmitt, Werner; Hitchings, George H. (October 1949). "The Synthesis of Pterorhodin (Rhodopterin)". Journal of the American Chemical Society. 71 (10): 3412–3416. doi:10.1021/ja01178a042.
  4. ↑ Schwalm, Patricia Ann (1981). Ultrastructural correlates to infrared reflectance in New World treefrogs (PhD). The University of Chicago.
  5. ↑ Blount, Christopher C. (2018). Near infrared reflectance in Anura (Thesis). The University of Manchester (United Kingdom).
  6. ↑ Viscontini, M.; Hummel, W.; Fischer, A. (1970). "Pigmente von Nereiden (Annelida, Polychaeten). 1., Vorläufige Mitteilung. Isolierung von Pterindimeren aus den Augen von Platynereis dumerilii (Audouin & Milne Edwards) 1833". Helvetica Chimica Acta. 53 (5): 1207–1209. doi:10.1002/hlca.19700530538.
  7. ↑ Hudon, Jocelyn; Muir, Alister D. (April 1996). "Characterization of the Reflective Materials and Organelles in the Bright Irides of North American Blackbirds (Icterinae)". Pigment Cell Research. 9 (2): 96–104. doi:10.1111/j.1600-0749.1996.tb00096.x. PMID   8857673.
  8. ↑ Andrade, Pedro; Carneiro, Miguel (August 2021). "Pterin-based pigmentation in animals". Biology Letters. 17 (8) 20210221. doi:10.1098/rsbl.2021.0221. PMC   8370806 . PMID   34403644. S2CID   237154759.
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