Castalagin

Castalagin
Chemical structure of castalagin
Names
Other names
Vescalagin (treatment)
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C41H26O26/c42-8-1-5-12(24(48)21(8)45)13-6(2-9(43)22(46)25(13)49)39(60)65-34-11(4-63-37(5)58)64-38(59)7-3-10(44)23(47)26(50)14(7)15-18-16(28(52)32(56)27(15)51)17-19-20(30(54)33(57)29(17)53)31(55)35(66-41(19)62)36(34)67-40(18)61/h1-3,11,31,34-36,42-57H,4H2/t11?,31-,34?,35?,36?/m1/s1[1]
    Key: UDYKDZHZAKSYCO-LSSWMSPRSA-N
  • C1C2C(C3C4C(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
Properties
C41H26O26
Molar mass 934.63 g/mol
Appearance off-white amorphous powder [2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Castalagin is an ellagitannin, a type of hydrolyzable tannin, found in oak and chestnut wood[3] and in the stem barks of Terminalia leiocarpa and Terminalia avicennoides.[4]

Castalagin is the diastereomer of vescalagin in C-1 of the glycosidic chain.[5] Castalagin/ vescalagin are the most abundant ellagitannins in white wine stored in oak barrels.[6] During aging of wines, these two compounds were progressively extracted from the wood and were transformed into new derivatives by chemical reactions.[7] Therefore, castalagin/ vescalagin and their derivatives contribute to the color and the taste of wines and spirits stored in oak barrels. [5]

  1. ^ "Castalagin". PubChem. 2017-07-29.
  2. ^ Yannai, Shmuel (2012-10-23). Dictionary of Food Compounds with CD-ROM, Second Edition. CRC Press. p. 861. ISBN 978-1-4200-8351-4.
  3. ^ Zahri, S; Belloncle, C; Charrier, F; Pardon, P; Quideau, S; Charrier, B (2007). "UV light impact on ellagitannins and wood surface colour of European oak (Quercus petraea and Quercus robur)". Applied Surface Science. 253 (11): 4985–9. Bibcode:2007ApSS..253.4985Z. doi:10.1016/j.apsusc.2006.11.005.
  4. ^ Shuaibu MN, Pandey K, Wuyep PA, et al. (November 2008). "Castalagin from Anogeissus leiocarpus mediates the killing of Leishmania in vitro". Parasitology Research. 103 (6): 1333–8. doi:10.1007/s00436-008-1137-7. PMID 18690475. S2CID 37480828.
  5. ^ a b Vivas N, Laguerre M, Pianet de Boissel I, Vivas de Gaulejac N, Nonier MF (April 2004). "Conformational interpretation of vescalagin and castalagin physicochemical properties". Journal of Agricultural and Food Chemistry. 52 (7): 2073–8. Bibcode:2004JAFC...52.2073V. doi:10.1021/jf030460m. PMID 15053554.
  6. ^ Marinov, M. G.; Dimitrova, E. D.; Puech, J. -L. (1997). "Kinetics of ellagitannin extraction from oak wood using white wine". Journal of Wine Research. 8: 29–40. doi:10.1080/09571269708718095.
  7. ^ Puech JL, Mertz C, Michon V, Le Guernevé C, Doco T, Hervé Du Penhoat C (May 1999). "Evolution of castalagin and vescalagin in ethanol solutions. Identification of new derivatives". Journal of Agricultural and Food Chemistry. 47 (5): 2060–6. Bibcode:1999JAFC...47.2060P. doi:10.1021/jf9813586. PMID 10552496.