Apiole: Difference between revisions

Apiol
Names
	IUPAC names 1-allyl-2,5-dimethoxy-; 3,4-methylenedioxybenzene
Identifiers
CAS Number	523-80-8 [clarification needed] ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL984002 ;
ChemSpider	21106259 ;
ECHA InfoCard	100.007.592
KEGG	C10429 ;
UNII	QQ67504PXO ;
CompTox Dashboard (EPA)	DTXSID4041236 ;
	InChI InChI=1S/C12H14O4/c1-4-5-8-6-9(13-2)11-12(10(8)14-3)16-7-15-11/h4,6H,1,5,7H2,2-3H3 Key: QQRSPHJOOXUALR-UHFFFAOYSA-N ; InChI=1/C12H14O4/c1-4-5-8-6-9(13-2)11-12(10(8)14-3)16-7-15-11/h4,6H,1,5,7H2,2-3H3 Key: QQRSPHJOOXUALR-UHFFFAOYAO;
	SMILES COc1cc(CC=C)c(OC)c2OCOc12;
Properties
Chemical formula	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)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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Revision as of 14:16, 30 July 2015

Apiole is a phenylpropene, also known as apiol, parsley apiol 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 apiole is also used for other closely related compounds, found in dill (dillapiole, 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene) and in fennel roots.

References

^ Azeez, Shamina; Krishnamurthy, K. (2008). Chemistry of Spices. Calicut, Kerala, India: Biddles Ltd. pp. 380 & 404. ISBN 9781845934057.
^ Shorter, Edward (1991). Women's Bodies: A Social History of Women's Encounter With Health, Ill-Health, and Medicine. New Brunswick, NJ: Transaction Publishers.
^ Amerio A; De Benedictis G; Leondeff J; et al. (Jan–Apr 1968). "Nephropathy due to apiol". Minerva Nefrol (in Italian). Vol. 15, no. 1. pp. 49–70.
^ Quinn LJ; Harris C; Joron GE (Apr 15, 1958). "Apiol poisoning". Can Med Assoc J. Vol. 78, no. 8. pp. 635–6.
^ Hermann K; Le Roux A; Fiddes FS (Jun 16, 1956). "Death from apiol used as abortifacient". Lancet. Vol. 270, no. 6929. pp. 937–9.
^ Sage-Femme Collective (2008). Natural Liberty: Rediscovering Self-Induced Abortion Methods. Sage-Femme Collective. ISBN 978-0964592001.
^ 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. Vol. 5, no. 12. pp. 1623–8.

External links

[1] Azeez, Shamina; 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). Vol. 15, no. 1. pp. 49–70.

[4] Quinn LJ; Harris C; Joron GE (Apr 15, 1958). "Apiol poisoning". Can Med Assoc J. Vol. 78, no. 8. pp. 635–6.

[5] Hermann K; Le Roux A; Fiddes FS (Jun 16, 1956). "Death from apiol used as abortifacient". Lancet. Vol. 270, no. 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. Vol. 5, no. 12. pp. 1623–8.

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-'''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]].<ref>{{cite book|last1=Azeez|first1=Shamina|last2=Krishnamurthy|first2=K.|title=Chemistry of Spices|year=2008|publisher=Biddles Ltd.|location=Calicut, Kerala, India|isbn=9781845934057|pages=380 & 404|url=http://books.google.com/books?id=5WY08iuJyawC&printsec=frontcover&dq=Chemistry+of+Spices&hl=en}}</ref> Heinrich Christoph Link, an [[apothecary]] in [[Leipzig]], discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley.<ref>{{cite book|last=Shorter|first=Edward|title= Women's Bodies: A Social History of Women's Encounter With Health, Ill-Health, and Medicine|year=1991|location=New Brunswick, NJ|publisher=Transaction Publishers}}</ref> In 1855 Joret and Homolle discovered that apiol was an effective treatment of [[amenorrea]] or lack of [[menstruation]].
+'''Apiole''' is a [[phenylpropene]], also known as apiol, [[parsley]] apiol or parsley camphor. It is found in the [[essential oils]] of [[celery]] leaf and all parts of [[parsley]].<ref>{{cite book|last1=Azeez|first1=Shamina|last2=Krishnamurthy|first2=K.|title=Chemistry of Spices|year=2008|publisher=Biddles Ltd.|location=Calicut, Kerala, India|isbn=9781845934057|pages=380 & 404|url=http://books.google.com/books?id=5WY08iuJyawC&printsec=frontcover&dq=Chemistry+of+Spices&hl=en}}</ref> Heinrich Christoph Link, an [[apothecary]] in [[Leipzig]], discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley.<ref>{{cite book|last=Shorter|first=Edward|title= Women's Bodies: A Social History of Women's Encounter With Health, Ill-Health, and Medicine|year=1991|location=New Brunswick, NJ|publisher=Transaction Publishers}}</ref> 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.<ref>{{cite news|author1=Amerio A|author2=De Benedictis G|author3=Leondeff J|title=Nephropathy due to apiol|journal=Minerva Nefrol|date=Jan–Apr 1968|volume=15|issue=1|pages=49–70|language=Italian|display-authors=etal}}</ref> Cases of death due to attempted abortion using apiol have been reported.<ref>{{cite news|author1=Quinn LJ|author2=Harris C|author3=Joron GE|date=Apr 15, 1958|title=Apiol poisoning|journal=Can Med Assoc J|volume=78|issue=8|pages=635–6}}</ref><ref>{{cite news|author1=Hermann K|author2=Le Roux A|author3=Fiddes FS|title=Death from apiol used as abortifacient|journal=Lancet|date=Jun 16, 1956|volume=270|issue=6929|pages=937–9}}</ref>
@@ Line 46: / Line 46: @@
 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.
+The name apiole 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 ==
 * [[Dillapiole]]
+* [[Exalatacin]]
 ==References==