Methyl everninate

Only two lichen species are used in large quantities as raw material for the perfume industry Evemia prunastri (L.) Ach. and Pseudevemia furfuracea (L.) Zopf. Up to 9000 tons of these two species have been processed annually (1986) at Grasse, the centre of the perfume industry in France (Moxham 1981). The ethanol extract of both lichens has a typical mossy flavour and is used not only as a component in certain perfumes ( Chypre ), but also as a fixative which keeps the flavour for a long time. The essential compounds originate from the depsides present in the lichens by hydrolysis, decarboxylation of the corresponding hydro-xyacids and alcoholysis. Orcinol and methyl everninate (sparassol) are compounds with the typical mossy odour. 

Deriv Methyl everninate, prisms (HjO), mp 67-68 °C, from everninic acid with the calculated amount of CHjNj in EtjO Lit Robertson and Stephenson 1932 ... 

Methyl everninate, Methyl 2-hydroxy-4-methoxy-6-methylbenzoate... 

Oakmoss Evernia prunastri Ethyl everninate (84), methyl /3-orcinolcarboxylate (85) 95,97... 

Sparassol. 2-Hydroxy-4-methoxy-6-methylbenzoic acid methyl ester 4-methoxy-2,6-cresotic acid methyl ester everninic acid methyl ester orseJJinic acid methyl ester 4-methyl ether. CMH1204 mol wt 196.20. C 61.21%, H 6.17%, O 32.62%. Antibiotic substance produced by the fungus Sparassis ramose Falck, Ber. 56, 2555 (1923). Also obtained in methanol extracts of the lichen Evernla prunasti-Stenhouse, Ann. 68, 55 (1848) Spath, Jeschki, Ber. 57, 471 (1924). Structure Fischer. Hoesch, Ann. 391, 347 (1912) Wedekind. Fleischer, Ber. 56, 2556 (1923). Synthesis <3. Nicollier el at. Helv. Chim. Acta 61, 2899 (1978). 

Everninic Acid 6-Hydroxy-2 methyla7iiaic acid, oraellinic acid -methyl ether, S-hydroxy-5-methoxy 4oluic acid)... 

React FeClj (EtOH) violet Deriv Methyl iso-everninate, mp 114°C (benzene), from iso-everninic acid with the calculated amount of CH2N2 in Et20 at 0°C Lit Robertson and Stephenson 1932 Roller and Pfeiffer 1933... 

Methyl 5-chloro-iso-everninate, Methyl 2-methoxy-4-hydroxy-5-chloro-6-methylbenzoate (5-Chlor-iso-everninsauremethylester, 2-Methoxy-4-hydroxy-5-chlorbenzoesauremethylester)... 

Until recently only two mixed orcinol P-orcinol depsides were known, namely obtusatic acid (210) and norobtusatic acid (211), but now a further four such compounds have been reported. These include 2-0-methylobtusatic acid (212) present in Xanthoparmelia tucsonensis 45) and evernine (213) 253), 3 -methylevernic acid (214) 252) and methyl 3 -methyllecanorate (215) 252) all obtained from Evernia prunastri. 

The spectral properties of depsides, in particular H-n.m.r. and mass spectra, provide a powerful probe in structural elucidation. C-n.m.r. spectroscopy has recently been used in the structural elucidation of ovoic acid (235) 194), 2",4-di-0-methylgyrophoric acid (236) (252), evernine (213) (255), 3 -methylevernic acid (214) (252) and methyl 3 -methyl-ecanorate (215) (252) but following a generalised study this technique 311, 312) will undoubtedly prove to be particularly important in the future. 

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