Pfizer Handbook of Microbial Metabolites 70 



John Frederick Grove, /. Chem. Soc, 4059 (1952). (Isola- 

 tion) 



J. R. Bartels-Keith and John Frederick Grove, Proc. Chem. 

 Soc, 398 (1959). (Structure) 



117 Rangiformic Acid, Cm,H;jsO,;, colorless needles, m.p. 106°, [a]i,-* 



+ 16.2°. 



CH3(CH2),3— CH— COOH 1 



CH — COOH j>Monomethyl ester 



CH2— COOHj 



Cladonia rangiformis Hoffm., C. viitis Sandst. 

 Masaru Aoki, J. Pharm. Soc. Japan 66A 52 (1946). 



118 Caperatic Acid, C2iH3g07, colorless leaflets, m.p. 132°, [aW° 



-3.85°. 



CH3(CH2)i3— CH— COOH 



I (one carboxyl group 



HO — C — COOH exists as the methyl 



j ester) 



CHj— COOH 



Parmelia caperata (L.), Nephromopsis stracheyi, f. 

 ectocarpisma Hue. 



Protocetraric acid also was present. 



Michizo Asano, Yukio Kameda and Osamu Tamemasa, /. 

 Pharm. Soc. Japan 61 203 (1944). 



119 Ungulinic Acid, C^.^H.^sOt;, colorless microcrystalline needles, 



m.p. 78-80°. 



Tentative structure of hydrate (ordinarily a y-lactone) : 



Ri— CH— COOH I Ri=C,6H3.3, R2=R3=H. 



R2— C— COOH II R2=Ci6H33, Ri=R3=H. 



R3— C— COOH Mi R3=Ci6H33, R,=R2=H. 



I 

 OH 



Polyporus betulinus 



J. H. Birkinshaw, E. N. Morgan and W. P. K. Findlay, 

 Biochem. J. 50 509 (1952). 



Sidonie Marcus, ibid. 50 516 (1952). 



