Perillic alcohol

Tho known constituents of ginger grass oil are the terpenes, diuen-tane, d-a-phellandreoo and rf-limonene, together with geraniol, ana an alonboJ which is identical with that obtained by the reduction of porUlio aldehyde, and which is known as perillic alcohol. 

It was separated from geraniol, which accompanies it in ginger-grass oil by treatment with concentrated formic acid, which destroys the geraniol, but does not attack the perillic alcohol. It has the following characters —... 

CHjOH Perillic alcohol. CH2CI Chloride. CH, Litnoueiie. 

By reduction with zinc-dust and acetic acid it yields the acetic ester of perillic alcohol, from which the alcohol itself is separated by saponification. 

Tumorigenesis is a complex multistep process influenced by many factors. There are some population-based studies indicating that a diet rich in isoprenoids play a role in the ability to avoid cancers [61]. In various experiments and test systems, some mono- and sesquiterpenes showed activity, where peril alcohol and D-limonene were of greatest interest. a-Bisabolol, the anti-inflammatory compound of chamomile oil, showed a strong time- and dose-dependent cytotoxic effect on glial cells [61]. p-Caryophyllene showed some potentiating effect on the anticancer activity of ot-humulene, isocaryophyUene, and paclitaxel on various cell lines [53]. Further studies are necessary to evaluate the anticancer potential of thymoquinone [53]. 

Peril alcohol, 2997 Perilla argata, 2981 Perillaldehyde, 2976, 2981 Perillyl alcohol, 4115, 4139,4140 Peripheral neurons, 64 Peripheral neuropathies, 4079 Periplaneta... 

Carvone is also present in small amount. The principal constituents of the oil, however, are geraniol and perillic alcohol, CjjHxgO. 

An alcohol of the formula Cj Hj O was isolated from oil of ginger-grass by Schimmel Co., and described by them as dihydrocuminic alcohol. It has, however, now been shown by Semmler and Zaar not to have the constitution assigned to it by Schimmel Co., but to be identical with the alcohol obtained by reducing perillic aldehyde, Cj<,H 40, the aldehyde characteristic of the essential oil of PerUla nankinensis. 

By oxidation this alcohol yields perillic aldehyde which forms a semi-carbazone, melting at 199° to 200°, and perillic acid, melting at 130° to 131°. It also yields a naphthyl-urethane, melting at 146° to 147°. 

When perillic acid is dissolved in five times its weight of amyl alcohol and is reduced by sodium at the boiling temperature, dihydro-perillic acid, CjoH Oj, is obtained. This acid melts at 107° to 109° C. By the reduction of its methyl ester by means of sodium, dihydroperillic alcohol is fornned, which is a liquid with a rose odour and having the following characters —... 

Myrtenal, C oH, 0, is an aldehyde found in the oil of Perilla nankin-ensis, associated with perillic aldehyde. It is also formed by the reduction of myrtenol, an alcohol of the formula CjpH,gO, occurring in oil of myrtle leaves. Myrtenal has the following characters —... 

Limonene and perillic acid remarkably reduced the lung metatastatic tumour nodule formation by 65 and 67%, respectively however, perillyl alcohol was considerably more potent than limonene against breast cancer [284, 302], rat mammary cancer and pancreatic tumours [288]. Phase 1 studies of d-limo-nene [303, 304] and phase I and phase II [305-311] studies of perillyl alcohol revealed dose-limiting toxicities nausea, vomiting, anorexia, unpleasant taste and eructation, and thus a maximum tolerated dose for perillyl alcohol was determined [305]. 

As mentioned before, a Pseudomonas incognita was isolated by enrichment technique on the monoterpene alcohol linalool that was also able to grow on geraniol, nerol and limonene [36]. The metabolism of limonene by this bacterium was also investigated [37]. After fermentation the medium yielded as main product a crystallic acid, perillic acid, together with unmetabolised limonene, and some oxygenated compounds dihydrocarvone, carvone, carveol, p-menth-8-en-1 -ol-2-one, p-menth-8-ene-1,2-diol or p-menth-1 -ene-6,9-diol (structure not fully elucidated) and finally / -isopropenyl pimelic acid. 

The same group has also isolated a strain of Pseudomonas putida-arvilla (PL-strain) from limonene and (+)-a-pinene as the sole carbon source that was capable of growing on (+)-limonene, (+)-a-pinene, (-)-a-pinene, / -pinene, 1-p-menthene, 3-p-menthene and p-cymene as substrates [75]. Limonene was degraded to perillyl alcohol, perillaldehyde and perillic acid. 

Alcohols can be O-methylated with diazomethane in the presence of a protic acid such as fluoroboric acid 210 Meerwein and Hinz211 showed that zinc chloride was an effective catalyst in 1930 and trifluoroborane later found favour 212 An alcohol adsorbed onto neutral silica gel undergoes O-methylation213 and the method can be used on a moderate scale [Scheme 4.117]214 though the perils of preparing diazomethane on a moderate scale must be the cause of some trepidation When tin(Il) chloride is used as the catalyst selective mono-0-methyla-tion of a l 2-diol can be achieved [Scheme 4 118] 215... 

Lo WK, Chan KT, Leung AC, Pang SW, Tse CY. Sclerosing peritonitis complicating prolonged use of chlorhexidine in alcohol in the connection procedure for continuous ambulatory peritoneal dialysis. Peril Dial Int 1991 ll(2) 166-72. 

The thermal decomposition of salts of fluorinated acids gives two different types of products, depending on the reaction conditions and the type of cation. When the decarboxylation of alkali and alkaline earth metal salts is carried out in the presence of proton donors, such as water, alcohol, aniline, pyridine or other basic solvents, the product of the reaction is a fluorocarbon hydride. This is a general procedure for the preparation of 1 //-peril uoroalkanes.62... 

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