Notholaenic acid

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Notholaenic acid
Chemical structure of notholaenic acid
Names
IUPAC name
2-hydroxy-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]benzoic acid
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.069.726 Edit this at Wikidata
UNII
  • InChI=1S/C17H18O5/c1-21-13-7-4-11(5-8-13)3-6-12-9-14(22-2)10-15(18)16(12)17(19)20/h4-5,7-10,18H,3,6H2,1-2H3,(H,19,20)
    Key: QTSHPXKETKYZMV-UHFFFAOYSA-N
  • InChI=1S/C17H18O5/c1-21-13-7-4-11(5-8-13)3-6-12-9-14(22-2)10-15(18)16 (12)17(19)20/h4-5,7-10,18H,3,6H2,1-2H3,(H,19,20)
    Key: QTSHPXKETKYZMV-UHFFFAOYSA-N
  • COC1=CC=C(C=C1)CCC2=CC(=CC(=C2C(=O)O)O)OC
Properties
C17H18O5
Molar mass 302.326 g·mol−1
Melting point 149 to 150 °C (300 to 302 °F; 422 to 423 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Notholaenic acid is a dihydrostilbenoid found in the farina of some ferns of the genus Notholaena.[1] It has been shown to have anti-HSV-1 (Herpes simplex virus 1) activity at high concentrations in vitro.[2] It was artificially synthesized, starting from 3-benzyloxy-5-methoxybenzyl alcohol, in 1985.[3]

References

  1. ^ Wollenweber, Eckhard; Favre-Bonvin, Jean (1979). "Novel dihydrostilbene from fronds of Notholaena dealbata and Notholaena limitanea". Phytochemistry. 18 (7): 1243–1244. doi:10.1016/0031-9422(79)80153-3.
  2. ^ Rinehart, Kenneth L.; Tom G. Holt; Nancy L. Fregeau; Paul A. Keifer; George Robert Wilson; Thomas J. Perun Jr; Ryuichi Sakai; Anthony G. Thompson; Justin G. Stroh; Lois S. Shield; David S. Seigler; Li H. Li; David G. Martin; Cornelis J. P. Grimmelikhuijzen; Gerd Gäde (July–August 1990). "Bioactive Compounds from Aquatic and Terrestrial Sources". Journal of Natural Products. 53 (4): 771–792. doi:10.1021/np50070a001. PMID 2095373.
  3. ^ El-Feraly, Farouk S.; Cheatham, Steve F.; McChesney, James D. (1985). "Total Synthesis of Notholaenic Acid". Journal of Natural Products. 48 (2): 293–298. doi:10.1021/np50038a015.
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