Apiole is a

phenylpropene Phenylpropene is the organic compound with the formula C6H5CH2CH=CH2. It is a colorless liquid. The compound consists of a phenyl group attached to allyl. Phenylpropene isomerizes to trans-propenylbenzene. In plant biochemistry, the phenylprop ...

, also known as apiol, parsley apiol, or parsley camphor. Its chemical name is 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene. It is found in the

essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the o ...

s of

celery Celery (''Apium graveolens'') is a marshland plant in the family Apiaceae that has been cultivated as a vegetable since antiquity. Celery has a long fibrous stalk tapering into leaves. Depending on location and cultivar, either its stalks, lea ...

leaf and all parts of

parsley Parsley, or garden parsley (''Petroselinum crispum'') is a species of flowering plant in the family Apiaceae that is native to the central and eastern Mediterranean region (Sardinia, Lebanon, Israel, Cyprus, Turkey, southern Italy, Greece, Por ...

. Heinrich Christoph Link, an

apothecary ''Apothecary'' () is a mostly archaic term for a medical professional who formulates and dispenses '' materia medica'' (medicine) to physicians, surgeons, and patients. The modern chemist (British English) or pharmacist (British and North Ameri ...

Leipzig Leipzig ( , ; Upper Saxon: ) is the most populous city in the German state of Saxony. Leipzig's population of 605,407 inhabitants (1.1 million in the larger urban zone) as of 2021 places the city as Germany's eighth most populous, as wel ...

, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855 Joret and Homolle discovered that ''apiol'' was an effective treatment of

amenorrea Amenorrhea is the absence of a Menstrual cycle, menstrual period in a woman of reproductive age. Physiological states of amenorrhoea are seen, most commonly, during pregnancy and lactation (breastfeeding). Outside the reproductive years, there is ...

or lack of

menstruation Menstruation (also known as a period, among other colloquial terms) is the regular discharge of blood and mucosal tissue from the inner lining of the uterus through the vagina. The menstrual cycle is characterized by the rise and fall of hor ...

. In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders and as an abortifacient. It is an irritant and, in high doses, it can cause liver and kidney damage. Cases of death due to attempted abortion using apiole have been reported.

Hippocrates Hippocrates of Kos (; grc-gre, Ἱπποκράτης ὁ Κῷος, Hippokrátēs ho Kôios; ), also known as Hippocrates II, was a Greek physician of the classical period who is considered one of the most outstanding figures in the history of ...

wrote about parsley as an herb to cause an

abortion Abortion is the termination of a pregnancy by removal or expulsion of an embryo or fetus. An abortion that occurs without intervention is known as a miscarriage or "spontaneous abortion"; these occur in approximately 30% to 40% of pregn ...

. Plants containing apiole were used by women in the Middle Ages to terminate pregnancies. Now that safer methods of abortion are available, apiol is almost forgotten. According to a book called PIHKAL, Apiole had been used to synthesize a psychedelic amphetamine called

DMMDA 2,5-Dimethoxy-3,4-methylenedioxyamphetamine (DMMDA) is a psychedelic drug of the phenethylamine and amphetamine chemical classes. It was first synthesized by Alexander Shulgin and was described in his book '' PiHKAL''. Shulgin listed the dosage ...

Orthography

Apiole (always with the final 'e') is the correct spelling of the trivial name for 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene. Apiol, also known as liquid apiol or green oil of parsley, is the extracted

oleoresin Oleoresins are semi-solid extracts composed of resin and essential or fatty oil, obtained by evaporation of the solvents used for their production. The oleoresin of conifers is known as crude turpentine or gum turpentine, which consists of oil of ...

of parsley, rather than the distilled oil. Its use was widespread in the United States, often as ergoapiol or apergol, as an early form of birth control as well as for menstrual issues (and off label for abortions)until a highly toxic adulterated product containing apiol and

tri-ortho-cresyl phosphate Tricresyl phosphate (TCP), is a mixture of three isomeric organophosphate compounds most notably used as a flame retardant and as a plasticizer in manufacturing for lacquers and varnishes and vinyl plastics. Pure tricresyl phosphate is a colour ...

(also famous as the adulterant added to

Jamaican ginger Jamaica ginger extract, known in the United States by the slang name Jake, was a late 19th-century patent medicine that provided a convenient way to obtain alcohol during the era of Prohibition in the United States, Prohibition, since it contai ...

) was introduced on the American market. 1'-sulfoxy metabolite formation for apiole (3,4-OMe-safrole) is about 1/3 as active as safrole. No carcinogenicity was detected with parsley apiol or dill apiol in mice.

Other similarly named compounds

The name apiole is also used for a closely related compound found in

dill Dill (''Anethum graveolens'') is an annual herb in the celery family Apiaceae. It is the only species in the genus ''Anethum''. Dill is grown widely in Eurasia, where its leaves and seeds are used as a herb or spice for flavouring food. Growth ...

and in

fennel Fennel (''Foeniculum vulgare'') is a flowering plant species in the carrot family. It is a hardy, perennial herb with yellow flowers and feathery leaves. It is indigenous to the shores of the Mediterranean but has become widely naturalized ...

roots, the positional isomer (

dillapiole Dillapiole is an organic chemical compound and essential oil commonly extracted from dill weed, though it can be found in a variety of other plants such as fennel root. This compound is closely related to apiole, having a methoxy group positioned ...

, 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene. Exalatacin (1-allyl-2,6-dimethoxy-3,4-methylenedioxybenzene) is another positional isomer of apiole, found in the Australian plants '' Crowea exalata'' and '' Crowea angustifolia var. angustifolia''.

References

External links

Apiol chemical information from chemindustry.com
* {{Phenylpropene Phenylpropenes O-methylated phenylpropanoids Abortifacients Allyl compounds Benzodioxoles

Orthography

Other similarly named compounds

See also

References

External links