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 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 ...

s of

celery Celery (''Apium graveolens'' Dulce Group or ''Apium graveolens'' var. ''dulce'') is a cultivated plant belonging to the species ''Apium graveolens'' in the family Apiaceae that has been used as a vegetable since ancient times. The original wild ...

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 Greece, Morocco and the former Yugoslavia. It has been introduced and naturalisation (biology), naturalized in Eur ...

. Heinrich Christoph Link, an

apothecary ''Apothecary'' () is an Early Modern English, archaic English term for a medicine, medical professional who formulates and dispenses ''materia medica'' (medicine) to physicians, surgeons and patients. The modern terms ''pharmacist'' and, in Brit ...

Leipzig Leipzig (, ; ; Upper Saxon: ; ) is the most populous city in the States of Germany, German state of Saxony. The city has a population of 628,718 inhabitants as of 2023. It is the List of cities in Germany by population, eighth-largest city in Ge ...

, 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 Mucous membrane, mucosal tissue from the endometrium, inner lining of the uterus through the vagina. The menstrual cycle is characterized ...

. 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 (; ; ), also known as Hippocrates II, was a Greek physician and philosopher of the Classical Greece, classical period who is considered one of the most outstanding figures in the history of medicine. He is traditionally referr ...

wrote about parsley as an herb to cause an

abortion Abortion is the early termination of a pregnancy by removal or expulsion of an embryo or fetus. Abortions that occur without intervention are known as miscarriages or "spontaneous abortions", and occur in roughly 30–40% of all pregnan ...

. 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.

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 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 o ...

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 herb in the celery family Apiaceae. It is native to North Africa, Iran, and the Arabian Peninsula; it is grown widely in Eurasia, where its leaves and seeds are used as a herb or spice for flavouring ...

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