Notholaenic acid

Notholaenic acid

Names
IUPAC name 2-hydroxy-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]benzoic acid
Identifiers
CAS Number	72578-97-3
Jmol interactive 3D	Image
PubChem	3085829
InChI 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
SMILES COC1=CC=C(C=C1)CCC2=CC(=CC(=C2C(=O)O)O)OC
Properties
Chemical formula	C17H18O5
Molar mass	302.33 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).
Infobox references

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–Aug 1990). "Bioactive Compounds from Aquatic and Terrestrial Sources". Journal of Natural Products 53: 771–792. doi:10.1021/np50070a001. Retrieved 29 April 2012. Cite uses deprecated parameter |coauthors= (help); Check date values in: |date= (help)
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.