Perilla aldehyde

Perilla frutescens (L.) Britt. China 1-perilla, aldehyde, apigenin, luteolin, 3-p-coumarylglycoside-5-glucoside of cyanidin, 7-caffeyl-glucosides of apigenin and luteolin, anthocyanins.33-50 Antibacterial, antitussive, stomachic, antiseptic. 

In the essential oil, apart from cuminaldehyde, perilla aldehyde (4-(l-methyl-ethenyl)-l-cyclohexene-l-carboxaldehyde), cumin alcohol or 4-isopropylbenzyl alcohol, a-pinene and /3-pinene (21%), dipentene, p-cymene, /3-phellandrene and limonene (Fig. 11.1) have been reported by Baser et al. (1992). 

However, the composition of the volatile oil obtained from the herb also differs markedly from that of the seeds. Eleven components out of 21 are similar in both herb and seed oils, while some differences have been observed between the relative amounts of /J-pinene, a-terpinene, p-cymene, a-terpineol, perilla aldehyde, thymol, a-cis-bergamotene, acoradiene and... 

In Group 7 the a- and P-isomers of santalyl acetate (Elavis 09.034, FEMA 3007) are mentioned. These compounds have a characteristic sandalwood-like odour and a bitter-sweet taste. Additional compounds in this group are perilla aldehyde (Flavis 05.117, FEMA 3557) with fatty, spicy notes and safranal (Flavis 05.104, FEMA 3389) with a characteristic saffron-like odour and taste. 

Perilla aldehyde underwent the Wittig reaction,396 and also reacted with 1-methoxy-l-thiophenoxycyclopropane to give (186).397 The 5,6-epoxide of carvone... 

One can also start directly from p-pinene (142). This was opened to the nitro compound 599 with nitrous acid, titanium tetrachloride then giving perilla aldehyde (600). Photochemical addition of 5e-phenyl p-toluenesulfonate to P-pinene yielded an addition product in 91% yield, oxidative deselenylation of which gave 94% of the 7-substituted menthadiene 601, but the latter was not converted to the oxygenated menthadiene. ... 

A second example is provided by perilla aldehyde whose odor has been described as including green, cumin and almond notes. Its far infrared spectrum has peaks at 156 and 234 closely matching ones in the cumin pattern its peaks at 234 and 420 are near those at 237 and 422 in the almond pattern, and its peaks at 156, 277 and 420 are not far from those at 159, 282, and 425 in the green pattern. 

Matsumoto T, Takaoka K, Watanabc C (1987) Acaricides, insecticides and insect repellents ctmtaining benzaldehyde or perilla aldehyde. Patem JP-87 176437 870715... 

Saturated aliphatic aldehydes generally give low yields in the azlactone synthesis. at,/3-Unsaturated aldehydes such as cinnamaldehyde, of-nr-amylcinnamaldehyde, and perilla aldehyde, which cannot undergo an aldol condensation, react satisfactorily (65-80% yields). 2-Thio-phenealdehyde diethylacetal gives yields as satisfactory as those from the... 

---