Orsellinic acid

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Orsellinic acid
IUPAC name

2,4-dihydroxy-6-methylbenzoic acid

Identifiers
CAS number 480-64-8 N
PubChem 68072
ChemSpider 61385 YesY
KEGG C01839 YesY
ChEBI CHEBI:32807 YesY
ChEMBL CHEMBL457583 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H8O4
Molar mass 168.14 g/mol
Melting point 175 °C; 347 °F; 448 K
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Orsellinic acid, more specifically o-orsellinic acid, is a phenolic acid. It is of importance in the biochemistry of lichens, from which it can be extracted.[1]

Chemistry

It can be prepared by the oxidation of orsellaldehyde.[2]

This is also produced when everninic acid and ramalic acid is boiled with barium hydroxide. It forms colorless crystals in the form of needles which on rapid heating melt with decomposition in the neighborhood of 175 °C.[3]

Biosynthesis of orsellinic acid from polyketides

References

  1. ↑ Nolan, T. J.; Keane, J.; Davidson, V. E. (1940). "Chemical constituents of the lichen Parmelia latissima Fee". Scientific Proceedings of the Royal Dublin Society, Series A 22: 237–239. 
  2. ↑ Kang, Ying; Mei, Yan; Du, Yuguo; Jin, Zhendong (2003). "Total Synthesis of the Highly Potent Anti-HIV Natural Product Daurichromenic Acid along with Its Two Chromane Derivatives, Rhododaurichromanic Acids A and B". Organic Letters 5 (23): 4481–4484. doi:10.1021/ol030109m. PMID 14602030. 
  3. ↑ Russell, R.; Kemmelmeier, C (1990). "Neutral, alkaline and difference ultraviolet spectra of secondary metabolites from Penicillium and other fungi, and comparisons to published maxima from gradient high-performance liquid chromatography with diode-array detection.". Journal of Chromatography 511: 195–221. doi:10.1016/S0021-9673(01)93285-6. PMID 2211911. 

encyclopaedia of organic chemistry sananda chaterjee

Phenolic acids and their glycosides
Monohydroxybenzoic acids
Aglycones
Glycosides
  • p-Hydroxybenzoic acid glucoside
Dihydroxybenzoic acids
Trihydroxybenzoic acids
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