Foeniculoside I

Foeniculoside I is a stilbenoid. It is a glucoside of the stilbene trimer cis-miyabenol C. It can be found in Foeniculi fructus (fruit of Foeniculum vulgare).[1]

Foeniculoside I
Chemical structure of foeniculoside I
Names
IUPAC name
3-{(2S,2′R,3S,3′R)-6,6′-Dihydroxy-2,2′-bis(4-hydroxyphenyl)-4-[(E)-2-(4-hydroxyphenyl)ethen-1-yl]-2,2′,3,3′-tetrahydro[3,4′-bi-1-benzofuran]-3′-yl}-5-hydroxyphenyl β-D-glucopyranoside
Systematic IUPAC name
(12S,13R,14S,15S,16R,42R,43R,52S,53S,6E)-16-(Hydroxymethyl)-42,52-bis(4-hydroxyphenyl)-42,43,52,53-tetrahydro-4,5(3,4)-bis([1]benzofurana)-1(2)-oxana-3(1,3),8(1)-dibenzenaoctaphan-6-ene-13,14,15,35,46,56,84-heptol
Other names
cis-Miyabenol C 11a-O-β-D-glucopyranoside
Identifiers
3D model (JSmol)
  • InChI=1S/C48H42O14/c49-22-38-43(56)44(57)45(58)48(62-38)59-34-17-27(16-31(53)18-34)40-41-35(19-33(55)21-37(41)61-46(40)24-5-11-29(51)12-6-24)42-39-26(4-1-23-2-9-28(50)10-3-23)15-32(54)20-36(39)60-47(42)25-7-13-30(52)14-8-25/h1-21,38,40,42-58H,22H2/b4-1+/t38-,40-,42+,43-,44+,45-,46+,47-,48-/m1/s1
    Key: SZKVNSODIJRAET-AKFYMKAISA-N
  • OCC1OC(OC2=CC(=CC(O)=C2)C2C(OC3=CC(O)=CC(C4C(OC5=C4C(\C=C\C4=CC=C(O)C=C4)=CC(O)=C5)C4=CC=C(O)C=C4)=C23)C2=CC=C(O)C=C2)C(O)C(O)C1O
Properties
C48H42O14
Molar mass 842.850 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. Ono, Masateru; Ito, Yasuyuki; Kinjyo, Junei; Yahara, Shoji; Nohara, Toshihiro; Niiho, Yujiro (1995). "Four New Glycosides of Stilbene Trimer from Foeniculi Fructus (Fruit of Foeniculum vulgare MILLER)". Chemical & Pharmaceutical Bulletin. 43 (5): 868–871. doi:10.1248/cpb.43.868. INIST:3610745


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