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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
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
  • 180579-78-6[1] N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:88363 Y
ChemSpider
  • 8560889
  • 10385447
  • 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).

See also edit

References edit

  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. Bibcode:1997PChem..44.1365M. 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.

External links edit

  • 5-8'-Dehydrodiferulic acid at phenol-explorer.eu

diferulic, acid, diferulic, acid, cyclic, type, diferulic, acid, predominant, diferulic, acid, sugar, beet, pulp, also, found, barley, maize, bran, diferulic, acid, also, been, identified, covalently, linked, carbohydrate, moieties, arabinogalactan, protein, f. 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 NamesPreferred IUPAC name 2E 2 5 E 2 Carboxyethen 1 yl 2 hydroxy 3 methoxyphenyl 3 4 hydroxy 3 methoxyphenyl prop 2 enoic acidOther names 8 5 DiFAFerulic acid 8 5 dehydrodimer8 5 diFA open form 8 5 DiFA5 8 Dehydrodiferulic acidIdentifiersCAS Number 180579 78 6 1 N3D model JSmol Interactive imageChEBI CHEBI 88363 YChemSpider 8560889PubChem CID 10385447InChI 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 NInChI 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 SITOFEAGBFSMILES O C O C C c1cc OC c O c c1 C C c2ccc O c OC c2 C O OPropertiesChemical formula C 20H 18O 8Molar mass 386 356 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox referencesSee also editDecarboxylated 8 5 diferulic acidReferences edit 8 5 Diferulic acid Chemical Substance Information J GLOBAL jglobal jst go jp 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 Bibcode 1997PChem 44 1365M doi 10 1016 S0031 9422 96 00699 1 Hernanz D Nunez V Sancho AI Faulds CB Williamson G Bartolome B Gomez Cordoves 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 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 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 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 External links edit5 8 Dehydrodiferulic acid at phenol explorer eu Retrieved from https en wikipedia org w index php title 8 5 27 Diferulic acid amp oldid 1196420039, wikipedia, wiki, book, books, library,

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