Apiol

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Apiol

IUPAC name	1-allyl-2,5-dimethoxy- 3,4-methylenedioxybenzene
Identifiers
CAS number	[523-80-8]
SMILES	C=CCC1=C(OC)C2=C (OCO2)C(OC)=C1
Properties
Molecular formula	C₁₂H₁₄O₄
Molar mass	222.23 g/mol
Melting point	30 °C
Boiling point	294 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Apiol is an organic chemical compound, also known as parsley apiol, apiole or parsley camphor. It is found in parsley seeds and the essential oil 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 menstruation disorders. It is an irritant and in high doses it is toxic and can cause liver and kidney damage.

Hippocrates wrote about parsley as a herb to cause an abortion. This effect was caused by the apiol.

Apiol was used by women in the Middle Ages to terminate pregnancies.^{[citation needed]} Its use was widespread in the USA, often as ergoapiol or apergol, until a highly toxic adulterated product containing apiol and tri-orthocresyl phosphate (also famous as the adulterant added to Jamaican ginger) was introduced on the American market.

The toxic effects of pure crystalline apiol are disputed. It causes a "relatively safe abortion" in pregnant women if taken in small quantities. It also restores the cycle of menstruation. A larger dose does not cause an abortion, it causes nausea and damages the liver and kidneys.^{[citation needed]}

Now that other methods of abortion are available apiol is almost forgotten in the West, but it is still produced and is used in the Middle East.^{[citation needed]}

The name apiol is also used for other closely related compounds, found in dill (dillapiole, 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene) and in fennel roots.

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[edit] References

The references in this article would be clearer with a different or consistent style of citation, footnoting, or external linking.

Edward Shorter: A history of women's bodies New York 1982 Bulletin géneral de thérapeutique médicale, No. 158, 1909 (A history of apiol and abortions)