Orsellinic acid

Orsellinic acid
IUPAC name 2,4-dihydroxy-6-methylbenzoic acid
Identifiers
CAS number	480-64-8 Y
PubChem	68072
ChemSpider	61385 Y
KEGG	C01839 Y
ChEBI	CHEBI:32807 N
ChEMBL	CHEMBL457583 Y
Jmol-3D images	Image 1
SMILES O=C(O)c1c(cc(O)cc1O)C
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) Y Key: AMKYESDOVDKZKV-UHFFFAOYSA-N Y 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
Properties
Molecular formula	C8H8O4
Molar mass	168.14 g/mol
Melting point	175 °C, 448 K, 347 °F
N acid (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]

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.