Apiole
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Preferred IUPAC name
4,7-Dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole
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| Other names
5-Allyl-4,7-dimethoxybenzo[d][1,3]dioxole
1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene (no longer recommended) |
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3D model (Jmol)
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| ChemSpider | |
| ECHA InfoCard | 100.007.592 |
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| Properties | |
| C12H14O4 | |
| Molar mass | 222.23 g/mol |
| Density | 1.151 g/mL |
| Melting point | 30 °C (86 °F; 303 K) |
| Boiling point | 294 °C (561 °F; 567 K) |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 (what is   ?) |
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| Infobox references | |
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 leaf and all parts of parsley. Heinrich Christoph Link, an apothecary in Leipzig, 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 apiol have been reported.
Hippocrates wrote about parsley as a herb to cause an abortion. 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.
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 of parsley, rather than the distilled oil. Its use was widespread in the USA, often as ergoapiol or apergol, 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.
The name apiole is also used for a closely related compound found in dill and in fennel 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.
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