Oil of Parsley

All parts of the parsley plant, Carum petroseltnum, Benth. et Hook., yield a volatile oil, but that from the leaf and root are not commercial articles. Parsley oil of commerce is invariably obtained from the fruit, which yields from 2 to 6 per cent. 

Parsley is cultivated in all temperate climates, but the fruit comes into the market chiefly from Germany and France. 

Oil of parsley, obtained by distillation of the fruit, is a yellowish or yellowish-green, thick liquid, specific gravity 1.017 to 1.100, optical rotation 5 to 10°, refractive index 1.488 to 1.507. 

Parsley fruit contains a fairly large quantity of apiole with the corresponding glucoside, apiin. Apiole or parsley camphor is a methoxymyristicin, and is the 2 5-dimethoxy-3 4-methylene ether of 

1- allyl benzene it is a crystalline substance at ordinary temperatures, melting-point 30°, boiling point 294°/760 mm. and 179°/33 mm., specific gravity at 15°, 1.178. It is volatile in steam, and occurs in both the French and German oils, sometimes in the latter in such large quantities as to crystallise out at the ordinary temperature. 

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MYRISTICIN In moderate amounts in dill, carrot, celery, fennel, mace and nutmeg (no more than 10% tops). Makes up about 40% of the oil of parsnip and can reach up to 50-60% of the oil of parsley leaves and seeds. Give nutmeg a rest folks It just don t have it when compared to parsley and parsnip. 

This phenol ether has been isolated from French oil of parsley. It is a crystalline compound of the formula Cj3Hjg04, which can be separated by freezing the oil and drying the crystals on porous plates for twenty-four bouts, and recrystallising the product several times from alcohol. Its constitution is as follows —... 

Apiol, the principal constituent of oil of parsley, is an allyl-dimethoxy-... 

SYNTHESIS Apiole, as the crystalline essential oil l-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene, is isolated directly from commercial Oil of Parsley, by... 

The essential oil that corresponds to DMMDA is, of course, apiole from the Oil of Parsley, which again ties together the spice world and the amphetamine world. And there is isoapiole, also a natural thing. This pair represents the ring-substitution pattern of one of the ten essential oils and DMMDA is one of the ten essential amphetamines. 

The tetramethoxy pattern. The third and last of the tetra-oxygenated essential oils, is l-allyl-2,3,4,5-tetraniethoxybenzene. This is present as a minor component in the oil of parsley, but it is much more easily obtained by synthesis. It, and its iso-compound, and the animation product, are discussed under the last of theTen Essential Amphetamines, TA. 

EXTENSIONS AND COMMENTARY This is pretty sparse information upon which to build a picture of biological activity. First, the synthesis was done by someone else and, as I have not been able to find where the notes are, this will be the one recipe in the footnote without explicit directions incorporated. The procedure used was exactly the same as that described for DMMDA, except that the starting material was dillapiole rather than apiole. The dillapiole was obtained by the careful fractionation of Oil of Dill (as opposed to the isolation of apiole from the careful fractionation of Oil of Parsley). Isomerization to isodillapiole, nitration with tetra-nitromethane to give 1 -(2,3-dimethoxy-4,5-methylenedioxyphenyl)-2-nitropropene, and its reduction with LAH in ether to give 2,3-dimethoxy-4,5-methylenedioxyamphetamine hydrochloride (DMMDA-2) proceeded in a precisely analogous manner to the preparation of DMMDA. 

Simon, J.E. and Quinn, J. (1988) Characterization of essential oil of parsley. Journal of Agricultural and Food Chemistry 36, 467-472. 

This procedure is an advance procedure for the extraction of apiole from oil of parsley. This process utilizes vacuum distillation. 

Figure 013. Advanced setup for vacuum fractional distillation for the isolation of apiole from commercial oil of parsley.

Parsley oil is used in medicine. Crystalline apiole, yellow and white apioles, and oil of parsley when given intravenously exert an equal degree of toxicity, the essential oil being the most regular in its action. Bull, Sci. Pharm. 1910 17, 7, via Y.B. ofPharm. 1910, 207)... 

On account of the dill-apiole it contains, of which it forms an abundant source, the oil has strong physiological action, although it is not so active as oil of parsley, which contains apiole. The yield of oil from this plant has been studied by Borde, Bull. Sci. Pharmacol. 1909, 16, 132, via Chem. Centrulbl. 1909, 80, i, 1566) who collected the plants at different times with the following results ... 

The oil from the leaves has an aromatic, somewhat pungent odom and a deep yellow colour. It is interesting to note that it is heavier than that from the fruit, whereas, in the related oil of parsley the fruit oi contains the larger proportion of the heavy ingredients. The fruits especially when air-dried, gave a pleasant-smelling oil. 

Oil of Parsley. Parsley seed oil. Volatile oil from parsley seeds Petroselinum hortenSe, Hoffm. (P. sativum Hoffm., Carum petroselinum Benth. Hook.), Umbeliiferae. Constit. Chiefly apiot terpene, f-pinene< ). 

SYNTHESIS Apiole, as the crystalline essential oil 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene, is isolated directly from commercial Oil of Parsley, by careful fractional distillation. It is the fraction that boils at 165-167 °C at 27 mm/Hg. A solution of 19.8 g apiole in a mixture of 43 g KOH and 60 mL hot EtOH was heated in the steam bath for 24 h. With vigorous stirring, it was diluted with H20, at a rate which the crystals that formed spontaneously could accumulate from the turbidity that was generated. When no more H20 could be added (there was persistent oiling out of material) the reaction mixture was filtered to give 12.1 g of an amber solid material. This was recrystallized from 20 mL boiling hexane, which was filtered while hot to remove insolubles. From the cooled filtrate, there was obtained 9.3 g of 2,5-dimethoxy-3,4-methylenedioxy-1-propenylbenzene, isoapiole, as pale cream-colored solids. 

The 2,5-dimethoxy-3,4-methylenedioxy pattern. The parent allyl benzene is apiole (with a final "e") or parsley camphor, and it is the major component of parsley seed oil. Its conjugated isomer is called isoapiole, and they are valuable as the chemical precurors to the amination product, DMMDA. Whereas both of these essential oils are white solids, there is a green oily liquid that had been broadly used years ago in medicine, called green, or liquid apiol (without the final "e"). It comes from the seeds of parsley by ether extraction, and when the chlorophyll has been removed, it is known as yellow apiol. With the fats removed by saponification and distillation, the old term for the medicine was apiolin. I would assume that any of these would give rise to white, crystalline apiole on careful distillation, but I have never tried to do it. The commercial Oil of Parsley is so readily available. 

Petroselinic add (Z)-6-octadecenoic acid]. H3C-(CH2),o-CH=CH-(CH2)4-COOH, C,gH3402, Mr 282.47, mp. 32-33°C, bp. 215-217°C (0.2-0.3 kPa) soluble in organic solvents. P. was first found as the glycerol ester in the seed oil of parsley (Petro-selinum crispum), it is a characteristic component of the seed oils of umbelliferous and ivy plants. The fatty acids of these seed oils contain up to 87% P. (e.g. fat coriander oil, 75-80%). P. is also used as a starting material in oleochemistry. For nutritional-physiological aspects, see Lit.. ... 

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