Divaricatic acid

Divaricatic acid is a chemical compound with the molecular formula C₂₁H₂₄O₇. It is found in a variety of lichens, including some in the genera Evernia,^[1] and Lepraria,^[2] and Ramalina.^[3] It is classified as a depside.

Divaricatic acid

Names
IUPAC name 2-Hydroxy-4-(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy-6-propylbenzoic acid
Identifiers
CAS Number	491-62-3
3D model (JSmol)	Interactive image
ChEBI	CHEBI:144147
ChEMBL	ChEMBL1965404
ChemSpider	329798
PubChem CID	371610
CompTox Dashboard (EPA)	DTXSID40197685
InChI InChI=1S/C21H24O7/c1-4-6-12-9-15(11-16(22)18(12)20(24)25)28-21(26)19-13(7-5-2)8-14(27-3)10-17(19)23/h8-11,22-23H,4-7H2,1-3H3,(H,24,25) Key: FSRDIJIAQPSMMR-UHFFFAOYSA-N
SMILES CCCC1=C(C(=CC(=C1)OC)O)C(=O)OC2=CC(=C(C(=C2)O)C(=O)O)CCC
Properties
Chemical formula	C21H24O7
Molar mass	388.416 g·mol−1
Appearance	Colorless crystalline needles
Melting point	129 °C (264 °F; 402 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Divaricatic acid forms colorless crystalline needles with a melting point of 129 °C.^[4]

Divaricatic acid has antibacterial properties against some Gram positive bacteria, such as Bacillus subtilis, Staphylococcus epidermidis, Streptococcus mutans, and Enterococcus faecium.^[5] Since it also has activity against methicillin-resistant Staphylococcus aureus (MRSA) with a potency equivalent to that of vancomycin, it has been suggested as a potential treatment for MRSA.^[5] It also has molluscicidal activity against Biomphalaria glabrata (ram's horn snail) and antiparasitic activity against cercariae of Schistosoma mansoni (blood fluke).^[6]

References

1. Asahina, Yasuhiko; Hirakata, Teruo (1932). "Lichen substances. XV. Divaricatic acid". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen. 65B: 1665–1668. doi:10.1002/cber.19320651007.{{cite journal}}: CS1 maint: multiple names: authors list (link)
2. Lendemer, James C. (2011). "A taxonomic revision of the North American species of Lepraria s.l. That produce divaricatic acid, with notes on the type species of the genus L. Incana". Mycologia. 103 (6): 1216–1229. doi:10.3852/11-032. PMID 21642343.
3. Moreira, Antônio; Braz-Filho, Raimundo; Mussi-Dias, Vicente; Vieira, Ivo (2015). "Chemistry and Biological Activity of Ramalina Lichenized Fungi". Molecules. 20 (5): 8952–8987. doi:10.3390/molecules20058952. PMC 6272487. PMID 25996207.
4. Hesse, O. (1897). "On lichen materials". Ber. Dtsch. Chem. Ges. 30: 357–366. doi:10.1002/cber.18970300172.
5. Oh, Jong Min; Kim, Yi Jeong; Gang, Hyo-Seung; Han, Jin; Ha, Hyung-Ho; Kim, Hoon (2018). "Antimicrobial Activity of Divaricatic Acid Isolated from the Lichen Evernia mesomorpha against Methicillin-Resistant Staphylococcus aureus". Molecules. 23 (12): 3068. doi:10.3390/molecules23123068. PMC 6320781. PMID 30477128.
6. Silva, H.A.M.F.; Siqueira, W.N.; Sá, J.L.F.; Silva, L.R.S; Martins, M.C.B.; Aires, A.L.; Amâncio, F.F.; Pereira, E.C.; Albuquerque, M.C.P.A; Melo, A.M.M.A.; Silva, N.H. (2018). "Laboratory assessment of divaricatic acid against Biomphalaria glabrata and Schistosoma mansoni cercariae". Acta Tropica. 178: 97–102. doi:10.1016/j.actatropica.2017.09.019. PMID 29097241.