Apterin

Apterin is a furanocoumarin and 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 and Zizia aptera.[1][2]

Apterin
Names
IUPAC name
(8S,9R)-8-[2-(β-D-Glucopyranosyloxy)propan-2-yl]-9-hydroxy-8,9-dihydro-2H-furo[2,3-h][1]benzopyran-2-one
Systematic IUPAC name
(8S,9R)-9-Hydroxy-8-(2-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl)-8,9-dihydro-2H-furo[2,3-h][1]benzopyran-2-one
Identifiers
3D model (JSmol)
ChemSpider
  • 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 checkY
    Key: ALEQYOXVXJKFOM-KTZZUYPUSA-N checkY
  • 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
  • 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
C20H24O10
Molar mass 424.402 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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Infobox references

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. Steck, Warren; Wetter, L.R. (1974). "Apterin, an unusual glucoside of Zizia aptera". Phytochemistry. 13 (9): 1925–1927. doi:10.1016/0031-9422(74)85117-4.
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