Vitisin C - Misplaced Pages

For other uses, see Vitisin.

Vitisin C
Names
Chemical structure of vitisin C
Preferred IUPAC name (2S,2S,3R,3S,4E,6S,6S)-2,3,6-Tris(4-hydroxyphenyl)-2,2,3,3,6,6-hexahydro-2(3,4),3(3,5),6(4,3)-tris(benzofurana)-1,7(1)-dibenzenaheptaphan-4-ene-1,1,2,6,7,7-hexol
Identifiers
CAS Number	180580-73-8
3D model (JSmol)	Interactive image Interactive image
ChEMBL	ChEMBL442911
ChemSpider	17301998
PubChem CID	16145527
UNII	M2HXT5SWE2
CompTox Dashboard (EPA)	DTXSID10583213
InChI InChI=1S/C56H42O12/c57-35-10-4-29(5-11-35)54-50(33-19-38(60)23-39(61)20-33)49-32(18-42(64)26-47(49)67-54)3-1-28-2-16-46-44(17-28)52(56(66-46)31-8-14-37(59)15-9-31)45-25-43(65)27-48-53(45)51(34-21-40(62)24-41(63)22-34)55(68-48)30-6-12-36(58)13-7-30/h1-27,50-52,54-65H/b3-1+/t50-,51-,52+,54+,55+,56-/m0/s1Key: WZKKRZSJTLGPHH-WHSOPTDBSA-N InChI=1/C56H42O12/c57-35-10-4-29(5-11-35)54-50(33-19-38(60)23-39(61)20-33)49-32(18-42(64)26-47(49)67-54)3-1-28-2-16-46-44(17-28)52(56(66-46)31-8-14-37(59)15-9-31)45-25-43(65)27-48-53(45)51(34-21-40(62)24-41(63)22-34)55(68-48)30-6-12-36(58)13-7-30/h1-27,50-52,54-65H/b3-1+/t50-,51-,52+,54+,55+,56-/m0/s1Key: WZKKRZSJTLGPHH-WHSOPTDBBK
SMILES OC(C=C1)=CC=C1(O2)(C3=CC(O)=CC(O)=C3)C4=C2C=C(O)C=C4/C=C/C5=CC((C6=C((C7=CC(O)=CC(O)=C7)(C8=CC=C(O)C=C8)O9)C9=CC(O)=C6)(C%10=CC=C(O)C=C%10)O%11)=C%11C=C5 Oc1ccc(cc1)4Oc2cc(O)cc(c24c3cc(O)cc(O)c3)\C=C\c%10ccc%11O(c5ccc(O)cc5)(c7cc(O)cc8O(c6ccc(O)cc6)(c78)c9cc(O)cc(O)c9)c%11c%10
Properties
Chemical formula	C₅₆H₄₂O₁₂
Molar mass	906.940 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

Vitisin C is a hydroxystilbenoid. It is a resveratrol tetramer found in plants of the genus Vitis (grapevines).

References

Ito, J (1996). "Absolute structures of new hydroxystilbenoids, vitisin C and viniferal, from Vitis vinifera 'Kyohou'". Tetrahedron. 52 (30): 9991–9998. doi:10.1016/0040-4020(96)00543-1.
Seya, K; Furukawa, K; Taniguchi, S; Kodzuka, G; Oshima, Y; Niwa, M; Motomura, S (2003). "Endothelium-dependent vasodilatory effect of vitisin C, a novel plant oligostilbene from Vitis plants (Vitaceae), in rabbit aorta". Clinical Science. 105 (1): 73–9. doi:10.1042/CS20020288. PMID 12605596. S2CID 41885739.

External links

Website of the Schröder group

Oligostilbenoids and their glycosides

Dimers

Trimers

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)

This article about an aromatic compound is a stub. You can help Misplaced Pages by expanding it.

Categories: