Fagopyrin

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Fagopyrin
Fagopyrin.svg
Fagopyrin 3D ball.png
Names
IUPAC name
1,3,4,6,8,13-Hexahydroxy-10,11-dimethyl-2,5-di(piperidin-2-yl)fenantro[1,10,9,8-opqra]peryleen-7,14-dion
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • 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,3-10H2,1-2H3
    Key: ROFJUMITFMRBRF-UHFFFAOYSA-N
  • 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
C40H34N2O8
Molar mass 670.718 g·mol−1
AppearanceRed pigment
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Fagopyrin is a term used for several closely related naturally occurring substances in the buckwheat plant. [1] Their chemical structure contains a naphthodianthrone skeleton similar to that of hypericin. [2]

Fagopyrin is located almost exclusively in the cotyledons of the buckwheat herb. When ingested, fagopyrins cause sensitivity to light. [3]

Related Research Articles

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Buckwheat, or common buckwheat, is a flowering plant in the knotweed family Polygonaceae cultivated for its grain-like seeds and as a cover crop. The name "buckwheat" is used for several other species, such as Fagopyrum tataricum, a domesticated food plant raised in Asia.

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The genus Fagopyrum is in the flowering plant family Polygonaceae. It includes some important food plants, such as F. esculentum (buckwheat) and F. tataricum. The genus is native to the Indian subcontinent, much of Indochina, and central and southeastern China. Species have been widely introduced elsewhere, throughout the Holarctic and parts of Africa and South America.

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<i>Fagopyrum tataricum</i> Species of plant

Fagopyrum tataricum, also known as Tartary buckwheat, green buckwheat, ku qiao, Tatar buckwheat, or bitter buckwheat, is a domesticated food plant in the genus Fagopyrum in the family Polygonaceae. With another species in the same genus, common buckwheat, it is often counted as a cereal, but the buckwheats are not closely related to true cereals.

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Phenylacetaldehyde is an organic compound used in the synthesis of fragrances and polymers. Phenylacetaldehyde is an aldehyde that consists of acetaldehyde bearing a phenyl substituent; the parent member of the phenylacetaldehyde class of compounds. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is an alpha-CH2-containing aldehyde and a member of phenylacetaldehydes.

<span class="mw-page-title-main">2-Methoxy-4-vinylphenol</span> Chemical compound

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<span class="mw-page-title-main">Epicatechin gallate</span> Chemical compound

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<i>Fagopyrum cymosum</i> Species of grass

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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.