Notholaenic acid

Notholaenic acid

Names
IUPAC name 2-hydroxy-4-methoxy-6-[2-(4-methoxyphenyl)ethyl]benzoic acid
Identifiers
CAS Number	72578-97-3
3D model (JSmol)	Interactive image
ChemSpider	2342609
ECHA InfoCard	100.069.726
PubChem CID	3085829
UNII	M566RQH8Y7 Y
CompTox Dashboard (EPA)	DTXSID80222900
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 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	302.326 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). Infobox references

Notholaenic acid is a dihydrostilbenoid found in the farina of some ferns of the genus Argyrochosma (formerly part of Notholaena).

The compound was originally purified from the waxy frond exudate of Notholaena limitanea and Notholaena dealbata.^[1] Subsequent analysis showed that only N. limitanea var. mexicana secretes notholaenic acid, while other taxa reported to produce it in fact secreted isonotholaenic acid.^[2]

Notholaenic acid has been shown to have anti-HSV-1 (Herpes simplex virus 1) activity at high concentrations in vitro.^[3] It was artificially synthesized, starting from 3-benzyloxy-5-methoxybenzyl alcohol, in 1985.^[4]