Orsellinic acid

Orsellinic acid
IUPAC name

2,4-dihydroxy-6-methylbenzoic acid
Identifiers
CAS number 480-64-8 N
PubChem 68072
ChemSpider 61385 Y
KEGG C01839 Y
ChEBI CHEBI:32807 Y
ChEMBL CHEMBL457583 Y
Jmol-3D images Image 1
Properties
Molecular formula C8H8O4
Molar mass 168.14 g/mol
Melting point

175 °C, 448 K, 347 °F
 N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Orsellinic acid, more specifically o-orsellinic acid, is an organic acid. It is of importance in the biochemistry of lichens, from which it can be extracted.[1] It can also be prepared by the oxidation of orcyl aldehyde.[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]

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. 
Monohydroxybenzoic acids
Dihydroxybenzoic acids
Trihydroxybenzoic acids