Ampelopsin B

Ampelopsin B
Names

IUPAC name (1S,7S,11bS)-1,7-Bis(4-hydroxyphenyl)-1,6,7,11b-tetrahydro-2-oxadibenzo[cd,h]azulene-4,8,10-triol
Other names (+)-Ampelopsin B (−)-Ampelopsin B
Identifiers
CAS Number	130518-19-3^Y
ChEBI	CHEBI:76191
ChemSpider	4476716
Jmol interactive 3D	Image
PubChem	5318088
InChI InChI=1S/C28H22O6/c29-17-5-1-14(2-6-17)21-10-16-9-19(31)13-24-25(16)27(22-11-20(32)12-23(33)26(21)22)28(34-24)15-3-7-18(30)8-4-15/h1-9,11-13,21,27-33H,10H2/t21-,27-,28+/m0/s1 Key: JJCVXDDMIRXVJA-YNOBPPCASA-N InChI=1/C28H22O6/c29-17-5-1-14(2-6-17)21-10-16-9-19(31)13-24-25(16)27(22-11-20(32)12-23(33)26(21)22)28(34-24)15-3-7-18(30)8-4-15/h1-9,11-13,21,27-33H,10H2/t21-,27-,28+/m0/s1 Key: JJCVXDDMIRXVJA-YNOBPPCABK
SMILES Oc1ccc(cc1)[C@H]6c2c(cc(O)cc2O)[C@H]4c5c(cc(O)cc5O[C@@H]4c3ccc(O)cc3)C6
Properties
Chemical formula	C₂₈H₂₂O₆
Molar mass	454.48 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

Ampelopsin B is a stilbenoid dimer found in Ampelopsis glandulosa var. hancei (formerly Ampelopsis brevipedunculata var. hancei).^[1]^[2]

References

↑ Oshima, Y (1990). "Ampelopsins A, B and C, new oligostilbenes of Ampelopsis brevipedunculata var hancei". Tetrahedron 46 (15): 5121. doi:10.1016/S0040-4020(01)87819-4.
↑ Chemical determination of the absolute structures of resveratrol dimers, ampelopsins A, B, D and F. Yoshiaki Takaya, Ke-Xu Yan, Kenji Terashima, Junko Ito and Masatake Niwa, Tetrahedron, 2002, 58, pages 7259–7265, doi:10.1016/S0040-4020(02)00785-8

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

Glycosides or conjugates

Diptoindonesin A (C-glucoside of ε-viniferin)
Foeniculoside I (glucoside of miyabenol C), II, III and IV
Laevifonol (an ε-viniferin-ascorbic acid hybrid compound)
Laevifoside (O-glucoside of ampelopsin A)

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