Alpha-Viniferin
Basic information
- CAS
62218-13-7- Standard SMILES
Oc1ccc([C@H]2Oc3cc(O)cc4c3[C@@H]2c2cc(O)cc3c2[C@@H](c2cc(O)cc5c2[C@@H]4[C@H](c2ccc(O)cc2)O5)[C@H](c2ccc(O)cc2)O3)cc1- InChIKey
KUTVNHOAKHJJFL-ZSIJVUTGSA-N- Molecular formula
- C42H30O9
- Average molar mass
- 678.7 g/mol
- Monoisotopic mass
- 678.18898253
Overview
(+)-alpha-viniferin is a nine-membered macrocycle that incorporates three 6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuranyl moieties as part of the cyclic skeleton. It is isolated from Caragana chamlague Lamarck and exhibits significant inhibitory effect towards the enzyme acetylcholinesterase (EC 3.1.1.7). It has a role as an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an anti-inflammatory agent and a plant metabolite. It is a polyphenol, a member of 1-benzofurans and a macrocycle. It is functionally related to a resveratrol.
Names & identifiers
- Preferred name
- Alpha-Viniferin
- IUPAC
- (2R,3R,10R,11R,18S,19S)-3,11,19-tris(4-hydroxyphenyl)-4,12,20-trioxaheptacyclo[16.6.1.12,5.110,13.021,25.09,27.017,26]heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaene-7,15,23-triol
- English name
- alpha-viniferin
- Molecular formula
- C42H30O9
- Molecular weight
- 678.68
Names & synonyms
alpha-Viniferin62218-13-7(+)-Alpha-Viniferin53XER6FHLXDTXSID40211274(2R,3R,10R,11R,18S,19S)-3,11,19-tris(4-hydroxyphenyl)-4,12,20-trioxaheptacyclo[16.6.1.12,5.110,13.021,25.09,27.017,26]heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaene-7,15,23-triolCHEBI:66359Cyclonona(1,2,3-cd:4,5,6-c'd':7,8,9-c''d'')trisbenzofuran-4,9,14-triol, 2,2a,7,7a,12,12a-hexahydro-2,7,12-tris(4-hydroxyphenyl)-, (2R*,2aR*,7R*,7aR*,12S*,12aS*)-(2R,2aR,7R,7aR,12S,12aS)-2,7,12-tris(4-hydroxyphenyl)-2,2a,7,7a,12,12a-hexahydrobis[1]benzofuro[3',4':4,5,6;3'',4'':7,8,9]cyclonona[1,2,3-cd][1]benzofuran-4,9,14-triol(2R,2aR,7R,7aR,12S,12aS)-2,7,12-tris(4-hydroxyphenyl)-2,2a,7,7a,12,12a-hexahydrobis(1)benzofuro(3',4':4,5,6;3'',4'':7,8,9)cyclonona(1,2,3-cd)(1)benzofuran-4,9,14-triol(2R,3R,10R,11R,18S,19S)-3,11,19-tris(4-hydroxyphenyl)-4,12,20-trioxaheptacyclo(16.6.1.12,5.110,13.021,25.09,27.017,26)heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaene-7,15,23-triolRefChem:111402
Show more names
α-Viniferin
Properties
Computed structural properties
- XLogP
- 6.8
- Topological polar surface area
- 149 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 3
- Heavy atoms
- 51
- Formal charge
- 0
- Complexity
- 1,080
Physicochemical properties
- Melting point
- 222 · 222-224 °C
- Density
- 1.517 · 1.517±0.06 g/cm3(Predicted)
- pka
- 9.06 · 9.06±0.70(Predicted)
- form
- Solid
- color
- White to yellow
- Cosmetics Ingredients Functions
- UV FILTER
- FDA UNII
- 53 XER6FHLX · 53XER6FHLX
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Applications
Usesα-Viniferin is an anti-inflammatory compound from Caragana chamlagu root[1].
Additional notes
DefinitionChEBI: A nine-membered macrocycle that incorporates three 6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydro-1-benzofuranyl moieties as part of the cyclic skeleton. It is isolated from Caragana chamlague Lamarck and exhibits significant inhibitory effect towa ds the enzyme acetylcholinesterase (EC 3.1.1.7).
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