Orsellinic acid

Orsellinic acid
Names
	Preferred IUPAC name 2,4-Dihydroxy-6-methylbenzoic acid
Identifiers
CAS Number	480-64-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:32807 ;
ChEMBL	ChEMBL457583 ;
ChemSpider	61385 ;
ECHA InfoCard	100.115.964
KEGG	C01839 ;
PubChem CID	68072;
UNII	11XLA0494B ;
CompTox Dashboard (EPA)	DTXSID20197385 ;
	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) Key: AMKYESDOVDKZKV-UHFFFAOYSA-N ; 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;
	SMILES 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). verify (what is ?) 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 through a Michael adduct:

This can also be produced by the hydrolysis of either everninic acid or ramalic 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.

References

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

[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.

[Merck-3] Merck Index (11th ed.). p. 1179-1180. 7009. o-Orsellinic acid.

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