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

HCID 375682

Notes Reactions

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Basic information

CAS: 62218-13-7
Standard SMILES: Oc1ccc(C2Oc3cc(O)cc4c3C2c2cc(O)cc3c2C(c2cc(O)cc5c2C4C(c2ccc(O)cc2)O5)C(c2ccc(O)cc2)O3)cc1
InChIKey: KUTVNHOAKHJJFL-UHFFFAOYSA-N
Molecular formula: C42H30O9
Average molar mass: 678.7 g/mol
Monoisotopic mass: 678.18898253

Overview

alpha-Viniferin has been reported in Caragana aurantiaca, Vitis vinifera, and Shorea gibbosa with data available.

Names & identifiers

Preferred name: 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
IUPAC: 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

SCHEMBL2721242CHEMBL1997745NSC655524AKOS032948514NSC-655524NCI60_019296Q4734921B0005-188645(2R,3R,10R,11R,18S,19S)-3,11,19-tris(4-hydroxyphenyl)-4,12,20-trioxaheptacyclo[16.6.1.1^{2,5.1^{10,13.0^{21,25.0^{9,27.0^{17,26]heptacosa-1(25),5,7,9(27),13,15,17(26),21,23-nonaene-7,15,23-triolα-Viniferinα-Viniferinalfa-Viniferin

Show more names

(+)-α-viniferinalpha-viniferin(2S,2aS,7aR,12aS)-2,2a,7,7a,12,12a-Hexahydro-2α,7β,12α-tri(p-hydroxyphenyl)cyclonona[1,2,3-cd:4,5,6-c'd':7,8,9-c''d'']trisbenzofuran-4,9,14-triol(5R,10S,15R,16R,18S,20R)-16,18,20-Tris(4-hydroxyphenyl)-4,5:9,10:14,15-tris(epoxymethano)-10,15-dihydro-5H-tribenzo[a,d,g]cyclononene-2,7,12-triol(2R,2aR,7R,7aR,12S,12aS)-2,2a,7,7a,12,12a-Hexahydro-2,7,12-tris(4-hydroxyphenyl)cyclonona[1,2,3-cd:4,5,6-c'd':7,8,9-c''d'']trisbenzofuran-4,9,14-triol(2S,2aS,7S,7aS,12R,12aR)-2,2a,7,7a,12,12a-Hexahydro-2,7,12-tris(4-hydroxyphenyl)cyclonona[1,2,3-cd:4,5,6-c'd':7,8,9-c''d'']trisbenzofuran-4,9,14-triolCyclonona[1,2,3-cd:4,5,6-c'd':7,8,9-c''d'']- trisbenzofuran-4,9,14-triol,2,2a,7,7a,12,12ahexahydro- 2,7,12-tris(4-hydroxyphenyl)-,(2R,2aR,7R,7aR,12S,12aS)-rel-(+)-

Database identifiers

CAS: 62218-13-7
PubChem CID: 375682
ChEMBL: CHEMBL1997745

Properties

Computed structural properties

XLogP: 6.8
Topological polar surface area: 149 Å²
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

Pharmacology

Cellular LocationsMembrane

Applications

Usesα-Viniferin is an anti-inflammatory compound from Caragana chamlagu root[1].

Suppliers53 total

成都乐美天医药科技有限公司17308096051 17308096051 · [email protected]

上海纯优生物科技有限公司15921393123 18302135232 · [email protected]

成都彼样生物科技有限公司18108052721 · [email protected]

杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]

江苏艾康生物医药研发有限公司025-025-66113011 15955137747 · [email protected]

Additional notes · 1 item

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).

Related reactions

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