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castalagin
Sign in to saveCastalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of Terminalia leiocarpa and Terminalia avicennoides.
Chemical data
- Formula
- C41H26O26
- Molecular weight
- 934.6 g/mol
- IUPAC name
- (1R,2R,20R,42S,46R)-7,8,9,12,13,14,25,26,27,30,31,32,35,36,37,46-hexadecahydroxy-3,18,21,41,43-pentaoxanonacyclo[27.13.3.138,42.02,20.05,10.011,16.023,28.033,45.034,39]hexatetraconta-5,7,9,11,13,15,23,25,27,29(45),30,32,34(39),35,37-pentadecaene-4,17,22,40,44-pentone
- SMILES
- C1[C@@H]2[C@H]([C@H]3[C@@H]4[C@@H](C5=C(C(=C(C(=C5C(=O)O4)C6=C(C(=C(C(=C6C(=O)O3)C7=C(C(=C(C=C7C(=O)O2)O)O)O)O)O)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8C9=C(C(=C(C=C9C(=O)O1)O)O)O)O)O)O
- InChIKey
- UDYKDZHZAKSYCO-JLQXGYSZSA-N
- XLogP
- 0.9
- Polar surface area
- 455 Ų
- H-bond donors
- 16
- H-bond acceptors
- 26
- Formal charge
- 0
via PubChem
Wikidata facts
- Mass
- 934.071230952
Show 4 more facts
- canonical SMILES
- O=C1OCC2OC(=O)C3=CC(O)=C(O)C(O)=C3C4=C(O)C(O)=C(O)C5=C4C(=O)OC(C6OC(=O)C7=C5C(O)=C(O)C(O)=C7C6O)C2OC(=O)C8=CC(O)=C(O)C(O)=C8C9=C(O)C(O)=C(O)C=C19
- isomeric SMILES
- O=C1OC[C@H]2OC(=O)c3cc(O)c(O)c(O)c3-c3c(O)c(O)c(O)c4c3C(=O)O[C@H]([C@H]3OC(=O)c5c-4c(O)c(O)c(O)c5[C@H]3O)[C@@H]2OC(=O)c2cc(O)c(O)c(O)c2-c2c1cc(O)c(O)c2O
- chemical formula
- C₄₁H₂₆O₂₆
- found in taxon
- Combretum malabaricum
Sources (1)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Sources
- Biosynthesis
- Derivatives
- References
Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood and in the stem barks of Terminalia leiocarpa and Terminalia avicennoides.
Castalagin is the diastereomer of vescalagin in C-1 of the glycosidic chain. Castalagin/ vescalagin are the most abundant ellagitannins in white wine stored in oak barrels. During aging of wines, these two compounds were progressively extracted from the wood and were transformed into new derivatives by chemical reactions. Therefore, castalagin/ vescalagin and their derivatives contribute to the color and the taste of wines and spirits stored in oak barrels.
Excerpted from Wikipedia’s “castalagin” article, available under the CC BY-SA 4.0 licence.