Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Ε-Viniferin: Difference between pages

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| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 461094439

| Name = ε-Viniferin

| Reference = <!-- <ref>{{cite web |url=http://www./ |title=Home |website=}}</ref> -->

| ImageFile = Epsilon-viniferin.svg

| ImageSize = 200px

| ImageCaption = (−)-''trans''-ε-Viniferin

| PIN = 5-<nowiki/>{(2''R'',3''R'')-6-Hydroxy-2-(4-hydroxyphenyl)-4-[(''E'')-2-(4-hydroxyphenyl)ethen-1-yl]-2,3-dihydro-1-benzofuran-3-yl}benzene-1,3-diol

| OtherNames = Viniferin<br />''epsilon''-Viniferin<br />(−)-''epsilon''-Viniferin<br />(−)-(''E'')-epsilon-viniferin<br />trans-ε-viniferin<br />(−)-Trans-epsilon-viniferin<ref>{{Cite journal | last1 = Yáñez | first1 = M. | last2 = Fraiz | first2 = N. | last3 = Cano | first3 = E. | last4 = Orallo | first4 = F. | title = (−)-Trans-ε-viniferin, a polyphenol present in wines, is an inhibitor of noradrenaline and 5-hydroxytryptamine uptake and of monoamine oxidase activity | doi = 10.1016/j.ejphar.2006.06.005 | journal = European Journal of Pharmacology | volume = 542 | issue = 1–3 | pages = 54–60 | year = 2006 | pmid = 16828740}}</ref><br /><nowiki>Iso-[epsilon]-viniferin</nowiki><ref>{{Cite journal

| last1 = Cornacchione | first1 = S.

| last2 = Sadick | first2 = N. S.

| last3 = Neveu | first3 = M.

| last4 = Talbourdet | first4 = S.

| last5 = Lazou | first5 = K.

| last6 = Viron | first6 = C.

| last7 = Renimel | first7 = I.

| last8 = De Quéral | first8 = D.

| last9 = Kurfurst | first9 = R.

| last10 = Schnebert | first10 = S.

| last11 = Heusèle | first11 = C.

| last12 = André | first12 = P.

| last13 = Perrier | first13 = E.

| title = In vivo skin antioxidant effect of a new combination based on a specific Vitis vinifera shoot extract and a biotechnological extract

| journal = Journal of Drugs in Dermatology

| volume = 6

| issue = 6 Suppl

| pages = s8–13

| year = 2007

| pmid = 17691204

}}</ref><br />''cis''-ε-viniferin<br />Cis-epsilon-viniferin<ref name=Kim>{{Cite journal | last1 = Kim | first1 = H. J. | last2 = Chang | first2 = E. J. | last3 = Cho | first3 = S. H. | last4 = Chung | first4 = S. K. | last5 = Park | first5 = H. D. | last6 = Choi | first6 = S. W. | doi = 10.1271/bbb.66.1990 | title = Antioxidative Activity of Resveratrol and Its Derivatives Isolated from Seeds of Paeonia lactiflora | journal = Bioscience, Biotechnology, and Biochemistry | volume = 66 | issue = 9 | pages = 1990–3 | year = 2002 | pmid = 12400706| s2cid = 24367582 | doi-access = free }}</ref>

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 62218-08-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 0K8Z2K6Y7O

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1224875

| SMILES = C1=CC(=CC=C1C=CC2=CC(=CC3=C2C(C(O3)C4=CC=C(C=C4)O)C5=CC(=CC(=C5)O)O)O)O

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| InChI = 1/C28H22O6/c29-20-7-2-16(3-8-20)1-4-18-11-24(33)15-25-26(18)27(19-12-22(31)14-23(32)13-19)28(34-25)17-5-9-21(30)10-6-17/h1-15,27-33H/b4-1+/t27-,28+/m1/s1

| InChIKey = FQWLMRXWKZGLFI-YVYUXZJTBS

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

|Section2={{Chembox Properties

| C=28 | H=22 | O=6

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

'''ε-Viniferin''' is a naturally occurring phenol, belonging to the [[stilbenoid]]s family. It is a [[resveratrol]] [[Dimer (chemistry)|dimer]].

It is found in ''[[Vitis vinifera]]''<ref>{{Cite journal | last1 = Privat | first1 = C. | last2 = Telo | first2 = J. O. P. | last3 = Bernardes-Genisson | first3 = V. | last4 = Vieira | first4 = A. | last5 = Souchard | first5 = J. P. | last6 = Nepveu | first6 = F. O. | doi = 10.1021/jf010676t | title = Antioxidant Properties oftrans-ε-Viniferin As Compared to Stilbene Derivatives in Aqueous and Nonaqueous Media | journal = Journal of Agricultural and Food Chemistry | volume = 50 | issue = 5 | pages = 1213–1217 | year = 2002 | pmid = 11853506}}</ref> grapevines,<ref>{{Cite journal | last1 = Langcake | first1 = P. | last2 = Pryce | first2 = R. J. | doi = 10.1007/BF02124034 | title = A new class of phytoalexins from grapevines | journal = Experientia | volume = 33 | issue = 2 | pages = 151–152 | year = 1977 | pmid = 844529| s2cid = 34370048 }}</ref> in [[wine]]s,<ref>{{Cite journal

| last1 = Vitrac | first1 = X.

| last2 = Bornet | first2 = A. L.

| last3 = Vanderlinde | first3 = R.

| last4 = Valls | first4 = J.

| last5 = Richard | first5 = T.

| last6 = Delaunay | first6 = J. C.

| last7 = Mérillon | first7 = J. M.

| last8 = Teissédre | first8 = P. L.

| doi = 10.1021/jf050122g

| title = Determination of Stilbenes (δ-viniferin, trans-astringin, trans-piceid, cis- and trans-resveratrol, ε-viniferin) in Brazilian Wines

| journal = Journal of Agricultural and Food Chemistry

| volume = 53

| issue = 14

| pages = 5664–5669

| year = 2005

| pmid = 15998130

}}</ref> in the Oriental medicinal plant ''[[Vitis coignetiae]]'' and in the stem bark of ''[[Dryobalanops aromatica]]''.<ref>{{Cite journal | last1 = Wibowo | first1 = A. | last2 = Ahmat | first2 = N. | last3 = Hamzah | first3 = A. S. | last4 = Sufian | first4 = A. S. | last5 = Ismail | first5 = N. H. | last6 = Ahmad | first6 = R. | last7 = Jaafar | first7 = F. M. | last8 = Takayama | first8 = H. | doi = 10.1016/j.fitote.2011.02.006 | title = Malaysianol A, a new trimer resveratrol oligomer from the stem bark of Dryobalanops aromatica | journal = Fitoterapia | volume = 82 | issue = 4 | pages = 676–681 | year = 2011 | pmid = 21338657}}</ref>

<br />Cis-epsilon-viniferin can be found in ''[[Paeonia lactiflora]]''.<ref name=Kim/>

It shows a human [[cytochrome P450]] enzymes inhibition activity.<ref>{{Cite journal | last1 = Piver | first1 = B. | last2 = Berthou | first2 = F. O. | last3 = Dreano | first3 = Y. | last4 = Lucas | first4 = D. L. | title = Differential inhibition of human cytochrome P450 enzymes by ε-viniferin, the dimer of resveratrol: Comparison with resveratrol and polyphenols from alcoholized beverages | doi = 10.1016/S0024-3205(03)00420-X | journal = Life Sciences | volume = 73 | issue = 9 | pages = 1199–1213 | year = 2003 | pmid = 12818727}}</ref>

== Glycosides ==

[[Diptoindonesin A]] is a ''C''-[[glucoside]] of ε-viniferin.

== See also ==

* [[Phenolic content in wine]]

== References ==

{{reflist}}

==External links==

*{{Commonscatinline|Epsilon-Viniferin}}

*[http://www.phenol-explorer.eu/compounds/584 e-viniferin on phenol-explorer.eu]

{{Oligostilbenoid}}

{{DEFAULTSORT:Viniferin, epsilon-}}

[[Category:Resveratrol oligomers]]

[[Category:Stilbenoid dimers]]

[[Category:Grape]]

[[Category:Wine chemistry]]

[[Category:Cytochrome P450 inhibitors]]

{{Aromatic-stub}}