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{{Short description|Family of organic compounds found in buckwheat}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 426218737
| Watchedfields = changed
⚫ | verifiedrevid = 455303239
| Name = Fagopyrin | Name = Fagopyrin
| ImageFile = Fagopyrin.svg | ImageFile = Fagopyrin.svg
⚫ | ImageAlt = Structural formula of fagopyrin
| ImageSize = 200px
| ImageFile1 = Fagopyrin 3D ball.png
⚫ | ImageName = Chemical structure of fagopyrin
| ImageAlt1 = Ball-and-stick model of the fagopyrin molecule
| IUPACName = <nowiki>1,3,4,6,8,13-hexahydroxy-10,11-dimethyl-2,5-di(piperidin-2-yl)fenantroperyleen-7,14-dion</nowiki> | IUPACName = 1,3,4,6,8,13-Hexahydroxy-10,11-dimethyl-2,5-di(piperidin-2-yl)fenantroperyleen-7,14-dion
| OtherNames = <!-- <br> --> | OtherNames = <!-- <br> -->
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo = | CASNo = 72393-03-4
| CASNo_Ref = | CASNo_Ref = {{cascite|changed|EPA}}
| CASOther = | ChemSpiderID = 4589856
| PubChem = | PubChem = 5488537
| 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 | 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
| StdInChI=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
| InChI =
| StdInChIKey = ROFJUMITFMRBRF-UHFFFAOYSA-N
| MeSHName =
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=40|H=34|N=2|O=8
| Formula = C<sub>40</sub>H<sub>34</sub>N<sub>2</sub>O<sub>8</sub>
| MolarMass = 670,71 g/mol | Appearance = Red pigment
| ExactMass = 670.231515 u
| Appearance = red pigment
| Density = | Density =
| MeltingPt = <!-- °C --> | MeltingPt =
| BoilingPt = <!-- °C --> | BoilingPt =
| Solubility = | Solubility =
}} }}
}} }}


'''Fagopyrin''' is a naturally occurring substance in the ] plant.<ref>{{cite journal | doi = 10.1007/BF00645366 | title = Fagopyrin, ein photodynamischer Farbstoff aus Buchweizen (Fagopyrum esculentum) | year = 1950 | last1 = Brockmann | first1 = Hans | last2 = Weber | first2 = Erhard | last3 = Sander | first3 = Elsbeth | journal = Die Naturwissenschaften | volume = 37 | pages = 43 | issue = 2 }}</ref> '''Fagopyrin''' is a term used for several closely related naturally occurring substances in the ] plant.<ref>{{cite journal | doi = 10.1007/BF00645366 | title = Fagopyrin, ein photodynamischer Farbstoff aus Buchweizen (Fagopyrum esculentum) | year = 1950 | last1 = Brockmann | first1 = Hans | last2 = Weber | first2 = Erhard | last3 = Sander | first3 = Elsbeth | journal = Die Naturwissenschaften | volume = 37 | pages = 43 | issue = 2 | bibcode=1950NW.....37...43B| s2cid = 29975083 }}</ref>
Their chemical structure contains a ] skeleton similar to that of ].<ref>{{cite journal | last1 = Tavčar Benković | first1 = Eva | last2 = Žigon | first2 = Dušan | last3 = Friedrich | first3 = Miha | last4 = Plavec | first4 = Janez | last5 = Kreft | first5 = Samo | year = 2014| title = Isolation, analysis and structures of phototoxic fagopyrins from buckwheat | journal = Food Chemistry | volume = 143 | pages = 432–439 | doi = 10.1016/j.foodchem.2013.07.118 | pmid = 24054263 }}</ref>
Its chemical structure contains a ] skeleton similar that of to ].{{Citation needed|date=February 2010}}

Fagopyrin is located almost exclusively in the ]s of the buckwheat herb. When ingested, fagopyrins cause ].<ref>{{cite journal |last1=Kreft |first1=S. |last2=Janeš |first2=D. |last3=Kreft |first3=I. |date=2013 |title=The content of fagopyrin and polyphenols in common and tartary buckwheat sprouts |journal=Acta Pharmaceutica |volume=63 |issue=4 |pages=553–60 |doi=10.2478/acph-2013-0031 |pmid=24451079 |doi-access=free }}</ref>


==References== ==References==
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==External links== ==External links==
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{{aromatic-stub}}
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Latest revision as of 12:50, 21 October 2024

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.

External links

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