8,5'-Diferulic acid

8,5′-Diferulic acid is a non cyclic type of diferulic acid. It is the predominant diferulic acid in sugar beet pulp.[2] It is also found in barley,[3] in maize bran[4] and rye.[5] 8,5′-Diferulic acid has also been identified to be covalently linked to carbohydrate moieties of the arabinogalactan-protein fraction of gum arabic.[6]

8,5′-Diferulic acid
Chemical structure of 8,5′-diferulic acid.
Names
Preferred IUPAC name
(2E)-2-{5-[(E)-2-Carboxyethen-1-yl]-2-hydroxy-3-methoxyphenyl}-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid
Other names
8,5′-DiFA
Ferulic acid 8-5-dehydrodimer
8,5′-diFA (open form)
8,5-DiFA
5-8′-Dehydrodiferulic acid
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
  • InChI=1S/C20H18O8/c1-27-16-9-11(3-5-15(16)21)8-14(20(25)26)13-7-12(4-6-18(22)23)10-17(28-2)19(13)24/h3-10,21,24H,1-2H3,(H,22,23)(H,25,26)/b6-4+,14-8+
    Key: DEPVSDIYICBTJE-SITOFEAGSA-N
  • InChI=1/C20H18O8/c1-27-16-9-11(3-5-15(16)21)8-14(20(25)26)13-7-12(4-6-18(22)23)10-17(28-2)19(13)24/h3-10,21,24H,1-2H3,(H,22,23)(H,25,26)/b6-4+,14-8+
    Key: DEPVSDIYICBTJE-SITOFEAGBF
  • O=C(O)\C=C\c1cc(OC)c(O)c(c1)/C(=C\c2ccc(O)c(OC)c2)C(=O)O
Properties
C20H18O8
Molar mass 386.356 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

See also

References
  1. "8,5'-Diferulic acid | Chemical Substance Information | J-GLOBAL". jglobal.jst.go.jp.
  2. Micard, V.; Grabber, J.H.; Ralph, J.; Renard, C.M.G.C.; Thibault, J.-F. (1997). "Dehydrodiferulic acids from sugar-beet pulp". Phytochemistry. 44 (7): 1365–1368. doi:10.1016/S0031-9422(96)00699-1.
  3. Hernanz, D; Nuñez, V; Sancho, AI; Faulds, CB; Williamson, G; Bartolomé, B; Gómez-Cordovés, C (2001). "Hydroxycinnamic acids and ferulic acid dehydrodimers in barley and processed barley". Journal of Agricultural and Food Chemistry. 49 (10): 4884–8. doi:10.1021/jf010530u. PMID 11600039.
  4. Bunzel, M; Funk, C; Steinhart, H (2004). "Semipreparative isolation of dehydrodiferulic and dehydrotriferulic acids as standard substances from maize bran". Journal of Separation Science. 27 (13): 1080–6. doi:10.1002/jssc.200301703. PMID 15495409.
  5. Andreasen, MF; Christensen, LP; Meyer, AS; Hansen, A (2000). "Content of phenolic acids and ferulic acid dehydrodimers in 17 rye (Secale cereale L.) varieties". Journal of Agricultural and Food Chemistry. 48 (7): 2837–42. doi:10.1021/jf991266w. PMID 11032481.
  6. Renard, D; Lavenant-Gourgeon, L; Ralet, MC; Sanchez, C (2006). "Acacia senegal gum: Continuum of molecular species differing by their protein to sugar ratio, molecular weight, and charges". Biomacromolecules. 7 (9): 2637–49. doi:10.1021/bm060145j. PMID 16961328.
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