Apiole is a
phenylpropene, 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. 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 ...
in
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.
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 pre ...
. 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, 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 (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, since it contained approximately 70% to 80% ethan ...
) 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, 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''.
See also
*
Dillapiole
*
Myristicin
References
External links
Apiol chemical information from chemindustry.com*
{{Phenylpropene
Phenylpropenes
O-methylated phenylpropanoids
Abortifacients
Allyl compounds
Benzodioxoles