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Fagopyrin

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Family of organic compounds found in buckwheat
Fagopyrin
Structural formula of fagopyrin
Ball-and-stick model of the fagopyrin molecule
Names
IUPAC name 1,3,4,6,8,13-Hexahydroxy-10,11-dimethyl-2,5-di(piperidin-2-yl)fenantroperyleen-7,14-dion
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C40H34N2O8/c1-13-11-17(43)23-25-19(13)20-14(2)12-18(44)24-26(20)28-27(25)29-31(35(45)21(15-7-3-5-9-41-15)37(47)33(29)39(23)49)32-30(28)34(40(24)50)38(48)22(36(32)46)16-8-4-6-10-42-16/h11-12,15-16,41-48H,3-10H2,1-2H3Key: ROFJUMITFMRBRF-UHFFFAOYSA-N
SMILES
  • O=C1C2=C(C3=C(O)C(C4CCCCN4)=C2O)C(C5=C6C(C)=CC(O)=C15)=C7C(C3=C(O)C(C8NCCCC8)=C9O)=C9C(C%10=C7C6=C(C)C=C%10O)=O
Properties
Chemical formula C40H34N2O8
Molar mass 670.718 g·mol
Appearance Red pigment
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Fagopyrin is a term used for several closely related naturally occurring substances in the buckwheat plant. Their chemical structure contains a naphthodianthrone skeleton similar to that of hypericin.

Fagopyrin is located almost exclusively in the cotyledons of the buckwheat herb. When ingested, fagopyrins cause sensitivity to light.

References

  1. Brockmann, Hans; Weber, Erhard; Sander, Elsbeth (1950). "Fagopyrin, ein photodynamischer Farbstoff aus Buchweizen (Fagopyrum esculentum)". Die Naturwissenschaften. 37 (2): 43. Bibcode:1950NW.....37...43B. doi:10.1007/BF00645366. S2CID 29975083.
  2. Tavčar Benković, Eva; Žigon, Dušan; Friedrich, Miha; Plavec, Janez; Kreft, Samo (2014). "Isolation, analysis and structures of phototoxic fagopyrins from buckwheat". Food Chemistry. 143: 432–439. doi:10.1016/j.foodchem.2013.07.118. PMID 24054263.
  3. Kreft, S.; Janeš, D.; Kreft, I. (2013). "The content of fagopyrin and polyphenols in common and tartary buckwheat sprouts". Acta Pharmaceutica. 63 (4): 553–60. doi:10.2478/acph-2013-0031. PMID 24451079.

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