Oil of patchouli

This sesquiterpene has not been found naturally. It is formed by the dehydration of the so-called patchouli camphor, a sesquiterpene alcohol, CjjHjgO, found in oil of patchouli. It has the following characters —... 

Oil of Patchouli. Patchouli oil. Essential oil from leaves of several Labiatae species. The commercial oil is obtained from the cultivated species, Pogoslemon cablin (Blanco) Benth. (P. patchouly Pellet, var suavis Hook, f.), Labiatae. Major constituent is patchouli alcohol (cj. i / minor constituents include patchoulene. azulene, eugeno], and several unidentified sesquiterpenes Pfau, Planner, Helv. 

S)-(+)-Carvone produces the typical odor and taste of caraway, whereas its (R)-(-)-enantiomer in the oil of spearmint from Mentha spicata (Labiatae), in contrast, smells like peppermint (p. 18). (-)-Patehoulol (also referred to as patehoulialeohol p. 40) smells intensely woody and earthy with a touch of camphor, similar to the natural oil of Patchouli used in perfumery, while the weak odor of the synthetically produced (+)-enantiomer is quite untypical. 

Patchouli alcohol. Patchouli oil comes from Pogostemonpatchouli and the main constituent is patchouli alcohol [5986-55-0] (105) or patchoulol. Another component of the essential oil is norpatchoulenol (106), a norsesquiterpene derivative as a minor (3—5%) constituent, important ia determining the overall odor of the essential oil (197). The price of patchouli oil ia 1995 was 20.90/kg from Indonesia (69). Alarge proportion of the oil (40—60%) is comprised of sesquiterpene hydrocarbons that do not have much odor value. World production of the oil was at about 750 t ia 1984. It is valuable ia perfumery bases because of its characteristic woody, herbaceous odor (198). 

Cadinene owes its name to its occuiTence in considerable quantity in oil of cade—which, of course, is not a true essential oil, but the product of destructive distillation. It is found in numerous essential oils, including those of patchouli, savin, galbanum, camphor, cedar wood. West Indian santal, juniper, and many others. Cadinene is best prepared as follows —... 

Sesquiterpenols are found in appreciable amounts in oils of ginger, carrot, valerian, patchouli and vetiver. The pharmacological effects are quite varied and general properties assigned to them include anti-inflammatory, stimulant to liver and glands, and tonic. 

A further study on the oxidation of terpenoid compounds by mammalian systems (c/. p. 62) has shown that patchoulol (298) is oxidized by rabbits to give a mixture of diol (299) and hydroxy-acid (300).129 Subsequent oxidative decarboxylation of (300) provided norpatchoulenol (301), the major odour carrier of patchouli oil. It has been suggested that a similar oxidative transformation of patchoulol occurs during the biosynthesis of norpatchoulenol in the plant.129 Cedrol (72) has also been oxidized by rabbits (c/. p. 62) and it is interesting to note that the hydroxylated products are... 

A useful synthesis (ref.ll)of patchouli alcohol, an important fragrant constituent of patchouli oil, from (+)-camphor, that onetime important natural product which was employed as a plasticiser for nitrocellulose (itself a semi-synthetic polymer), was complicated by structural revision of the sesquiterpene alcohol. Dihydrocarvone (14) obtained by saturation of the ring double bond in carvone, a major constituent of oil of spearmint has been employed for two very different sesquiterpenes, the ketone campherenone (15) and the alcohol, occidentalol (16). In the first case an enol acetate was converted to a bicyclic intermediate by earlier established methodology and the route emulated a plausible biogenetic sequence giving racemic campherenone (ref.12) as shown. Any chirality in (14) is apparently lost. 

Treatment of patchoulol (174 Scheme 62), an olfactive component of patchouli oil, with LTA gives rise to a mixture from which the almost pure ketone (175) is distilled. Thomas has postulated a free car-benium ion mechanism, but this reaction may be a legiospecific fragmentation facilitated by the fact that the proton on C(S) is oriented antiperiplanar to the C(l)- bond. 

Another similarity with vetiver is the fact that the odour of Patchouli Oil owes little to the major component. The natural isomer, (—)-patchouli alcohol has some patchouli character whereas its unnatural enantiomer is odourless. However, this odour contribution is a small part of the total and most of the intense character of patchouli comes from minor components such as nor-patchoulenol (7.84) and nor-tetrapatchoulol (7.85). These are both degradation products, probably the result of the fermentation stage and explaining the necessity of including this in the production process. Nor-patchoulenol was identified and characterised by Paul Tesseire of the fragrance company Roure-Bertrand-Dupont and nor-tetrapatchoulol by Braja Mookherjee of International Flavours and Fragrances. 

Extract of Whole Orange. See Orange (Citrus aurantium dulcis) oil Extract of patchouli. See Patchouli (Pogostemon cablin) extract Extracts (petroleum), heavy paraffinic distillate solvent. See Paraffin distillate Extract of yeast. See Yeast extract Extramalt Dark. See Malt extract Extra Olein. See Oleic acid Extra Super English Terra Alba. See Calcium sulfate... 

Sesquiterpenes, C15H24, were discovered in oils of cloves, calamus, cas-carilla, patchouli and cubebs by Gladstone. They were studied particularly by F. W. Semmler, professor in Greifswald and Breslau, who also worked on fenchone, and by Ruzicka. Wallach s suggestion that they are built up from three isoprene units (1887) is true for most of them. 

Another pertinent point is how much twig and leaf material can be used in juniper berry oil. In Indonesia, it is common practice to space individual layers of patchouli leaves in the distillation vessel with twigs of the gurjun tree. Gurjun balsam present in the twigs contains an essential oil that contaminates the patchouli oil. Can this be considered to constitute an adulteration or simply a tool required for the production of the oil ... 

Vetiver and patchouli are two oils of great importance in perfumery (Williams, 1996, 2004). Both contain complex mixtures of sesquiterpenoids, mostly with complex polycyclic structures (Sell, 2003). The major components of vetiver oil are a-vetivone (136), b-vetivone (137), and khusi-mol (119), but the most important components as far as odor is concerned are minor constituents such as khusimone (151), zizanal (152), and methyl zizanoate (153). Nootkatone (154) is an isomer of a-vetivone and is an important odor component of grapefruit. Patchouli alcohol (145) is the... 

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