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 ;
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 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

^ 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.
^ 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.
^ 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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[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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v t e Dihydrostilbenoids and their glycosides
Dihydrostilbenoids	Batatasin-III (3,3′-dihydroxy-5-methoxybibenzyl) Combretastatin and combretastatin B-1 Dihydro-resveratrol Isonotholaenic acid Lunularic acid Lunularin Notholaenic acid Tyrolobibenzyl A, B and C
Oligomeric forms	Bis(bibenzyls): 13,13'-O-Isoproylidenericcardin D Marchantin B and E Neomarchantin A Plagiochin E Riccardin H Macrocyclic bis(benzyls): Marchantin A and C Riccardin B and C Cyclic bibenzyl-dihydrophenanthrene derivative: Cavicularin