(−)-(9Z)-1,9-Heptadecadiene-4,6-diyn-3-ol as a Principal Component of the Resinous Sap of Evodiopanax innovans Nakai, Japanese Name, Takanotsume, and Its Role in an Ancient Golden Varnish of Japan

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Abstract
(−)-(9Z)-1,9-Heptadecadiene-4,6-diyn-3-ol was for the first time isolated in high yield (29%) from the resinous sap of Evodiopanax innovans Nakai, Araliaceae. This compound has been associated with the main polymerizable component of an ancient golden varnish. It has also been associated with a phytoalexin and a defense material which produces a water-insoluble coating film by photopolymerization under sunlight for a Takanotsume tree upon being wounded.