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Short chain ω-phenylalkanoic acids have long been known to occur in natural products. Phenylacetic, 3-phenylpropanoic and 3-phenylpropenoic (cinnamic) acids are found in propolis, mammalian exocrine secretions or plant fragrances. During a systematic study of the lipids from seeds of the plant Araceae,〔Schmid PC et al. Phytochemistry 1997, 45, 1173〕 the presence of 13-phenyltridecanoic acid as a major component (5-16% of total fatty acids)was discovered. Other similar compounds but with 11 and 15 carbon chain lengths and saturated or unsaturated were shown to be also present but in lower amounts. At the same time, the even carbon chain ω-phenylalkanoic acids of C10 up to C16 were discovered in halophilic bacteria.〔Caballeira NM et al., Lipids 1997, 32, 1271〕 ==ω-phenylalkanoic acid (x = 1 to 17)== Later, an exhaustive study of 17 genus of the subfamily Aroideae of Araceae revealed the presence of three major acids, 11-phenylundecanoic acid, 13-phenyltridecanoic acid and 15-phenylpentadecanoic acid in seed lipids.〔Meija J et al., Phytochemistry 2004, 65, 2229〕 Other odd carbon number acids from C7 to C23 were detected but in trace amounts. Similarly, two series of homologous odd carbon number monounsaturated ω-phenylalkanoic acids were found. Thus, it can be stated that all odd carbon chain ω-phenylalkanoic acids from C1 through C23 have been found in nature. Furthermore, even carbon chain ω-phenylalkanoic acids from C10 through C16 were also detected. Substituted phenylalkenoic acids are periodically encountered in nature. As an example, rubrenoic acids were purified from Alteromonas rubra, compounds which showed bronchodilatatoric properties.〔Holland GS et al., Chem Ind 1984, 850〕 Methyl phenylalkenoic acids (5 carbon chain) have been described from a terrestrial Streptomycete.〔Mukku VJ et al., Z Naturforsch 2002, 57b, 335〕 Serpentene, a similar polyunsaturated phenylalkenoic acid, is also produced by Streptomyces and was shown to have some antibacterial properties. Several serpentene-like compounds have also been isolated from the same bacterial source.〔Wenzel SC et al., J Nat Prod 2004, 67, 1631〕 Several bicyclic derivatives of linolenic acid were shown to be generated by alkali isomerization.〔Matikainen J et al., Tetrahedron Lett 2003, 59, 567〕 The stink from the stinkpot turtle (Sternotherus odoratus) contains at least four different foul smelling ω-phenylalkanoic acids, including phenylacetic acid, 3-phenylpropionic acid, 5-phenylpentanoic acid, and 7-phenylheptanoic acid. 抄文引用元・出典: フリー百科事典『 ウィキペディア（Wikipedia）』 ■ウィキペディアで「Phenyl alkanoic acids」の詳細全文を読む スポンサード リンク
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