Pfizer Handbook of Microbial Metabolites 672 



195b Non-4-cw-en-6,8-diynoic Acid, C9Hg02. 



HC^C— C=C— CH=CH— CH2— CH2— COOH 



CIS 



Drosophila subatrata 



198a Dec-2-<rans-en-4,6,8-triynoic Acid, C10H6O2. 



CH3— C^C— C = C— C=C— CH=CH— COOH 



frans 



Pleurotus ulmarius, Tricholoma paneolum 



201a Dec-2-frans-en-4,6,8-triynol, CioHgO. 



frans 

 CH3— C=C— C=C— C=C— CH=CH— CH2OH 



Pleurotus ulmarius 

 200a Deca-4,6,8-triyn-l,10-dioic Acid, C10H6O4. 



HOOC— C=C— C=C— C^C— CH2— CH2— COOH 

 Merulius lachrymans 

 219a Tetradec-5-cis-en-8,10,12-triyn-l,14-dioic Acid, C14H10O4. 



HOOC— C^C— C=C— C=C— CH— CH=CH— CH,— CHo— CH2— COOH 



CIS 



Poria sinuosa 



Four other polyacetylenes have been reported, complete 

 with physical properties : ^^ 



195c Drosophilin E (cis-Non-4-en-6,8-diynoic Acid), CgHgOa, light- 

 sensitive prisms, m.p. 35°, U.V. 279.5, 264, 250, 238, 227, 

 210 m/x. 



CIS 



HC=C— C^C— CH=CH— CH2— CHo— COOH 



Drosophila subatrata 



209a Drosophilin C (cis-Undec-3-en-5,7,10-triynoic Acid), CnHgOs, 

 colorless needles, slowly yellowing in light at 20°, m.p. 

 97.5-99°, U.V. 280.5, 264.5, 250.5, 238, 226.5, 210.5 m,x. 



HC=C— CH2— C^C— C=C— CH=CH— CH2— COOH 



Drosophila subatrata 



52 E. R. H. Jones, P. R. Leeming and W. A. Remers, /. Chem. Soc, 

 2257 (1960). 



