Orsellinic acid

Orsellinic acid
Names
	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	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]

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

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.
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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[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.