Anziaic acid is a
depside
A depside is a type of polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond. Depsides are most often found in lichens, but have also been isolated from higher plants, including species of the Ericaceae, L ...
found in lichens. It gives a red reaction in the
C test
A spot test in lichenology is a spot analysis used to help identify lichens. It is performed by placing a drop of a chemical on different parts of the lichen and noting the colour change (or lack thereof) associated with application of the chemical ...
. The two phenolic rings have a
pentyl
Pentyl is a five-carbon alkyl group or substituent with chemical formula -C5H11. It is the substituent form of the alkane pentane.
In older literature, the common non-systematic name amyl was often used for the pentyl group. Conversely, the name ...
side chain. It is an ester dimer of
olivetolic acid
Olivetolic acid is an organic compound that is an intermediate in the biosynthetic pathway of the cannabinoids in ''Cannabis sativa
''Cannabis sativa'' is an annual herbaceous flowering plant indigenous to Eastern Asia, but now of cosmopoli ...
.
Anziaic acid works as an antibacterial compound by inhibiting
topoisomerase
DNA topoisomerases (or topoisomerases) are enzymes that catalyze changes in the topological state of DNA, interconverting relaxed and supercoiled forms, linked (catenated) and unlinked species, and knotted and unknotted DNA. Topological issues i ...
.
Production
Anziaic acid has been artificially produced from olivetolic acid by benzylation of the ''O''-phenol positions, and then condensing with
trifluoroacetic anhydride
Trifluoroacetic anhydride (TFAA) is the acid anhydride of trifluoroacetic acid. It is the perfluorinated derivative of acetic anhydride.
Preparation
Trifluoroacetic anhydride was originally prepared by the dehydration of trifluoroacetic acid with ...
.
Properties
Anziaic acid is colourless. It can be dissolved in ethanol, ethanol-water mixture, or cyclohexane-benzene mixture.
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
In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in many ...
replaces a hydrogen in some of the hydroxy positions on the rings.[
]
Occurrence
Anziaic acid is found in Parmeliaceae
The Parmeliaceae is a large and diverse family of Lecanoromycetes. With over 2700 species in 71 genera, it is the largest family of lichen-forming fungi. The most speciose genera in the family are the well-known groups: '' Xanthoparmelia'' ( 822 ...
including ''Hypotrachyna
''Hypotrachyna'' is a genus of lichenized fungi within the family Parmeliaceae
The Parmeliaceae is a large and diverse family of Lecanoromycetes. With over 2700 species in 71 genera, it is the largest family of lichen-forming fungi. The m ...
'',[ '']Stereocaulon
''Stereocaulon'' is a genus of lichens. Members of ''Stereocaulon'' are commonly called snow lichens.
Species
*'' Stereocaulon alpinum''
*'' Stereocaulon apocalypticum''
*'' Stereocaulon arcticum''
*'' Stereocaulon arenarium''
*'' Stereocau ...
'',
References
{{Reflist
Carboxylate esters
Polyphenols
Lichen products