Orsellinic acid

Orsellinic acid
Names
Preferred IUPAC name
2,4-Dihydroxy-6-methylbenzoic acid
Identifiers
CAS Number
  • 480-64-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:32807 checkY
ChEMBL
  • ChEMBL457583 checkY
ChemSpider
  • 61385 checkY
ECHA InfoCard 100.115.964 Edit this at Wikidata
KEGG
  • C01839 checkY
PubChem CID
  • 68072
UNII
  • 11XLA0494B checkY
CompTox Dashboard (EPA)
  • DTXSID20197385 Edit this at Wikidata
InChI
  • 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
Chemical formula
 C8H8O4
Molar mass 168.148 g·mol−1
Melting point 176 °C (349 °F; 449 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
Chemical compound

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 through a Michael adduct:

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

This can also be produced by the hydrolysis of either everninic acid orramalic acid by boiling with barium hydroxide. When crystallized from acetone it forms crystalline needles with a melting point of 176 °C.[3] It also forms a crystalline hydrate with a melting point of 186-189 °C when crystallized from water.[3]

Orsellinic acid is biosynthesized by a polyketide pathway.

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. ^ a b Merck Index (11th ed.). p. 1179-1180. 7009. o-Orsellinic acid.