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 oils 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, ...

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, ...

. 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 Amer ...

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 ...

, 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 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 ...

. 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 o ...

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.

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 Apiol, also known as liquid apiol or green oil of parsley is the extracted oleoresin of parsley, rather than the distilled oil. Due to its similarity to the term apiole, care should be taken to avoid confusion. Apiol is an irritant and, in high do ...

, also known as liquid apiol or green oil of parsley, is the extracted oleoresin 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 (also famous as the adulterant added to Jamaican ginger) 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 plant, annual herbaceous, 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 fo ...

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, 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 ''Crowea exalata'', commonly known as small crowea or waxflower, is a flowering plant in the family Rutaceae and is endemic to the states of Queensland, New South Wales and Victoria in Australia. It is an attractive small shrub and is a popular g ...

'' and ''

Crowea angustifolia ''Crowea angustifolia'' is a flowering plant in the family Rutaceae, and is endemic to the south-west of Western Australia. It is an erect shrub growing to high by in diameter with white or pink flowers in spring. Description Crowea angustif ...

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