Anziaic acid

Anziaic acid is a depside found in lichens. It gives a red reaction in the C test. The two phenolic rings have a pentyl side chain. It is an ester dimer of olivetolic acid.^[1]

Anziaic acid

Names
IUPAC name 4-(2,4-Dihydroxy-6-pentylbenzoyl)oxy-2-hydroxy-6-pentylbenzoic acid
Identifiers
CAS Number	641-68-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:144192
ChEMBL	ChEMBL3134416
ChemSpider	31104179
PubChem CID	12306720
CompTox Dashboard (EPA)	DTXSID901169856
InChI InChI=1S/C24H30O7/c1-3-5-7-9-15-11-17(25)13-19(26)22(15)24(30)31-18-12-16(10-8-6-4-2)21(23(28)29)20(27)14-18/h11-14,25-27H,3-10H2,1-2H3,(H,28,29) Key: BEFYPHLCGVCBFF-UHFFFAOYSA-N
SMILES CCCCCC1=C(C(=CC(=C1)O)O)C(=O)OC2=CC(=C(C(=C2)O)C(=O)O)CCCCC
Properties
Chemical formula	C24H30O7
Molar mass	430.5 g/mol
Melting point	122 °C (252 °F; 395 K) dec
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Anziaic acid works as an antibacterial compound by inhibiting topoisomerase.^[2][3]

Production

Anziaic acid has been artificially produced from olivetolic acid by benzylation of the O-phenol positions, and then condensing with trifluoroacetic anhydride.^[1]

Properties

Anziaic acid is colourless. It can be dissolved in ethanol, ethanol-water mixture, or cyclohexane-benzene mixture.^[1]

Related

Perlatolic acid, dihydropicrolichenic acid, 2'-O-methylanziaic acid, 2-O-methylperlatolic acid, 2'-O-methylperlatolic and planaic acid are derivatives of anziaic acid, where a methyl group replaces a hydrogen in some of the hydroxy positions on the rings.^[1]

Occurrence

Anziaic acid is found in Parmeliaceae including Hypotrachyna,^[2] Stereocaulon,^[4] and Cetrelia,^[5]

References

1. Elix, J. A. (1974). "Synthesis of para-olivetol depsides". Australian Journal of Chemistry. 27 (8): 1767. doi:10.1071/CH9741767.
2. Cheng, Bokun; Cao, Shugeng; Vasquez, Victor; Annamalai, Thirunavukkarasu; Tamayo-Castillo, Giselle; Clardy, Jon; Tse-Dinh, Yuk-Ching (8 April 2013). "Identification of Anziaic Acid, a Lichen Depside from Hypotrachyna sp., as a New Topoisomerase Poison Inhibitor". PLOS ONE. 8 (4): e60770. Bibcode:2013PLoSO...860770C. doi:10.1371/journal.pone.0060770. PMC 3620467. PMID 23593306.
3. Kekuda, T.R Prashith; Lavanya, D .; Pooja, Rao (March 2019). "Lichens as promising resources of enzyme inhibitors: A review". Journal of Drug Delivery and Therapeutics. 9 (2S): 665–676. doi:10.22270/jddt.v9i2-s.2546.
4. Ramaut, J. L.; Serusiaux, E.; Brouers, M.; Corvisier, M. (1978). "Lichen Acids of the Stereocaulon ramulosum Group in Central East Africa". The Bryologist. 81 (3): 415. doi:10.2307/3242244. JSTOR 3242244.
5. Mark, Kristiina; Randlane, Tiina; Thor, Göran; Hur, Jae-Seoun; Obermayer, Walter; Saag, Andres (2019). "Lichen chemistry is concordant with multilocus gene genealogy in the genus Cetrelia (Parmeliaceae, Ascomycota)". Fungal Biology. 123 (2): 125–139. doi:10.1016/j.funbio.2018.11.013. PMID 30709518. S2CID 73439650.