Apiol

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Apiol
Skeletal formula
Ball-and-stick model
Identifiers
CAS number 523-80-8 [clarification needed] YesY
ChemSpider 21106259 YesY
UNII QQ67504PXO YesY
KEGG C10429 YesY
ChEMBL CHEMBL984002
Jmol-3D images Image 1
Properties
Molecular formula C12H14O4
Molar mass 222.23 g/mol
Density 1.151 g/mL
Melting point 30 °C
Boiling point 294 °C
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY (verify) (what is: YesY/N?)
Infobox references

Apiol is a phthalide, also known as parsley apiol, apiole or parsley camphor. It is found in the essential oils of celery leaf and all parts of parsley.[1] Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley.[2] 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.[3] Cases of death due to attempted abortion using apiol have been reported.[4][5]

Hippocrates wrote about parsley as a herb to cause an abortion.[6] Plants containing apiol were used by women in the Middle Ages to terminate pregnancies. 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. No carcinogenicity was detected with parsley apiol or dill apiol in mice.[7]

Now that safer methods of abortion are available, apiol is almost forgotten.

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.

See also[edit]

References[edit]

  1. ^ Krishnamurthy, K. (2008). Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. pp. 380 & 404. ISBN 9781845934057. 
  2. ^ Shorter, Edward (1991). Women's Bodies: A Social History of Women's Encounter With Health, Ill-Health, and Medicine. New Brunswick, NJ: Transaction Publishers. 
  3. ^ Amerio A; De Benedictis G; Leondeff J; et al. (Jan–Apr 1968). "Nephropathy due to apiol". Minerva Nefrol (in Italian) 15 (1). pp. 49–70. 
  4. ^ Quinn LJ; Harris C; Joron GE (Apr 15, 1958). "Apiol poisoning". Can Med Assoc J 78 (8). pp. 635–6. 
  5. ^ Hermann K; Le Roux A; Fiddes FS (Jun 16, 1956). "Death from apiol used as abortifacient". Lancet 270 (6929). pp. 937–9. 
  6. ^ Sage-Femme Collective (2008). Natural Liberty: Rediscovering Self-Induced Abortion Methods. Sage-Femme Collective. ISBN 978-0964592001. 
  7. ^ Phillips DH; Reddy MV; Randerath K (1984). "32P-post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. II. Newborn male B6C3F1 mice". Carcinogenesis 5 (12). pp. 1623–8. 

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