Foeniculoside I

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
CAS Number	168010-10-4
3D model (JSmol)	Interactive image
PubChem CID	101924276
InChI 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
SMILES 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
Chemical formula	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

Chemical compound

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]

References

^ 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

External links

Foeniculoside I at the Human Metabolome Database

Oligostilbenoids and their glycosides

Diptoindonesin C
Diptoindonesin F
Gnetin H
Hemsleyanol D
Isohopeaphenol
Laetevirenol A, B, C, D and E
Suffruticosol A and B
Viniferal
E-ω-viniferin
Z-ω-viniferin

Dimers

Diptoindonesin G
Jezonodione
B
Scirpusin A
Tibeticanol (piceatannol dimer)

Trimers

Amurensin B
Gnetin E
Gneyulin A
Johorenol A
Ampelopsin E
Vaticanol G

Tetramers:

Dibalanocarpol
Gnetin J (3"-hydroxygnetin E)
Gnetin K (3"-methoxygnetin E)
Gnetuhainin R (isorhapontigenin tetramer)
Laetevirenol F and G

Higher polymers
(five units or more)

Vaticanol D, H, I and J

Oligomeric forms
of resveratrol

Dimers	Amurensin A and H Ampelopsin A B D and F Balanocarpol Cyphostemmin A and B δ-viniferin ε-viniferin Gnetin A and C Leachinol F Malibatol A Pallidol Parthenocissin A Quadrangularin A Restrytisol A, B and C Vitisinol D
Trimers	α-viniferin Ampelopsin C Amurensin C, D and G Hopeanolin Malaysianol A Miyabenol C Resviniferin A and B trans-diptoindonesin B
Tetramers	Ampelopsin H Amurensin K Caraphenol B Carasinol B Flexuosol A Hopeaphenol Kobophenol A Miyabenol A Vaticanol B and C Vaticaphenol A Vitisin A B and C β-viniferin (cyclic resveratrol tetramer)
Pentamers	Amurensin E and F
Hexamers	Chunganenol
Higher polymers	γ-viniferin Valeriaphenol A