Apterin

Apterin

Names
IUPAC name (8S,9R)-9-hydroxy-8-[2-[2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropan-2-yl]-8,9-dihydrofuro[2,3-h]chromen-2-one
Identifiers
CAS Number	53947-89-0
ChemSpider	26286869
Jmol interactive 3D	Image
PubChem	15945058
InChI InChI=1S/C20H24O10/c1-20(2,30-19-16(26)15(25)13(23)10(7-21)28-19)18-14(24)12-9(27-18)5-3-8-4-6-11(22)29-17(8)12/h3-6,10,13-16,18-19,21,23-26H,7H2,1-2H3/t10-,13-,14-,15+,16-,18+,19+/m1/s1 Key: ALEQYOXVXJKFOM-KTZZUYPUSA-N InChI=1/C20H24O10/c1-20(2,30-19-16(26)15(25)13(23)10(7-21)28-19)18-14(24)12-9(27-18)5-3-8-4-6-11(22)29-17(8)12/h3-6,10,13-16,18-19,21,23-26H,7H2,1-2H3/t10-,13-,14-,15+,16-,18+,19+/m1/s1 Key: ALEQYOXVXJKFOM-KTZZUYPUBG
SMILES CC(C)([C@@H]1[C@@H](c2c(ccc3c2oc(=O)cc3)O1)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
Properties
Chemical formula	C20H24O10
Molar mass	424.399 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Apterin is a furanocoumarin. It is the glucoside of vaginol. It has been isolated from the root of plants in the family Apiaceae such as members of the genus Angelica, including the garden angelica^[1] and in Zizia aptera.^[2]

It is reported to dilate coronary arteries as well as block calcium channels.

References

1. Lemmich, John; Havelund, Svend; Thastrup, Ole (1983). "Dihydrofurocoumarin glucosides from Angelica archangelica and Angelica silvestris". Phytochemistry 22 (2): 553–5. doi:10.1016/0031-9422(83)83044-1.
2. Apterin, an unusual glucoside of Zizia aptera. Warren Steck and L. R. Wetter, Phytochemistry, Volume 13, Issue 9, September 1974, Pages 1925-1927, doi:10.1016/0031-9422(74)85117-4