Orsellinic acid
Names
Preferred IUPAC name
2,4-Dihydroxy-6-methylbenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.115.964
KEGG
UNII
  • InChI=1S/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12) checkY
    Key: AMKYESDOVDKZKV-UHFFFAOYSA-N checkY
  • InChI=1/C8H8O4/c1-4-2-5(9)3-6(10)7(4)8(11)12/h2-3,9-10H,1H3,(H,11,12)
    Key: AMKYESDOVDKZKV-UHFFFAOYAS
  • O=C(O)c1c(cc(O)cc1O)C
Properties
C8H8O4
Molar mass 168.148 g·mol−1
Melting point 175 °C (347 °F; 448 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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] It is a common subunit of depsides.

Chemistry

It can be prepared by the oxidation of orsellaldehyde,[2] or of a Michael adduct:

Ethyl acetoacetate condenses with ethyl crotonate to give ethyl dihydroorsellinate, followed by oxidation and hydrolysis

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.
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