Apiol and Apiole: Difference between pages

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444578066

| Name = Apiole

| ImageFile = Apiol structure.svg

| ImageAlt = Skeletal formula

| ImageFile1 = Apiol-3D-balls.png

| ImageAlt1 = Ball-and-stick model

| PIN = 4,7-Dimethoxy-5-(prop-2-en-1-yl)-2''H''-1,3-benzodioxole

| OtherNames = 5-Allyl-4,7-dimethoxybenzo[''d''][1,3]dioxole<br />1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene

|Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 1560118

| CASNo_Ref = {{cascite|correct|??}}

| CASNo_Comment = {{Clarify|date=July 2009}}

| UNII_Ref = {{fdacite|correct|FDA}}

| PubChem = 10659

| EC_number = 208-349-2

| ChEBI = 70353

}}

|Section2={{Chembox Properties

| Formula = C₁₂H₁₄O₄

| MolarMass = 222.23 g/mol

| Density = 1.151 g/mL

| MeltingPtC = 30

| BoilingPtC = 294

}}

'''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]]s 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=https://books.google.com/books?id=5WY08iuJyawC&q=Chemistry+of+Spices}}</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}}{{pn|date=September 2021}}</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 journal |last1=Amerio |first1=A |last2=De Benedictis |first2=G |last3=Leondeff |first3=J |last4=Mastrangelo |first4=F |last5=Coratelli |first5=P |title=La nefropatia da apiolo |trans-title=Nephropathy due to apiol |language=it |journal=Minerva Nefrologica |date=January 1968 |volume=15 |issue=1 |pages=49–70 |pmid=5736450 |oclc=100396864 }}</ref> Cases of death due to attempted abortion using apiole have been reported.<ref>{{cite journal |last1=Quinn |first1=Louis J. |last2=Harris |first2=Cecil |last3=Joron |first3=Guy E. |title=Apiol Poisoning |journal=Canadian Medical Association Journal |date=15 April 1958 |volume=78 |issue=8 |pages=635–636 |pmid=20325694 |pmc=1829842 }}</ref><ref>{{cite journal |last1=Hermann |first1=Kate |last2=Le Roux |first2=Anne |last3=Fiddes |first3=F.S. |title=Death from apiol used as abortifacient |journal=The Lancet |date=June 1956 |volume=267 |issue=6929 |pages=937–939 |doi=10.1016/s0140-6736(56)91522-7 |pmid=13320936 }}</ref>

[[Hippocrates]] wrote about parsley as an herb to cause an [[abortion]].<ref>{{cite book |author1=Sage-Femme Collective |title=Natural Liberty: Rediscovering Self-induced Abortion Methods |date=2008 |publisher=Natural Liberty |isbn=978-0-9645920-0-1 }}{{pn|date=September 2021}}</ref> 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{{fact|date=September 2021}} of the trivial name for 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene.<ref>{{cite journal |last1=Shulgin |first1=Alexander T. |title=Possible Implication of Myristicin as a Psychotropic Substance |journal=Nature |date=April 1966 |volume=210 |issue=5034 |pages=380–384 |doi=10.1038/210380a0 |pmid=5336379 |bibcode=1966Natur.210..380S |s2cid=4189608 |url=https://chemistry.mdma.ch/hiveboard/rhodium/pdf/myristicin.shulgin.pdf }}{{fv|date=September 2021}}</ref> [[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 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.<ref>{{cite journal |last1=Alajlouni |first1=Abdalmajeed M. |last2=Al_Malahmeh |first2=Amer J. |last3=Kiwamoto |first3=Reiko |last4=Wesseling |first4=Sebastiaan |last5=Soffers |first5=Ans E.M.F. |last6=Al-Subeihi |first6=Ala A.A. |last7=Vervoort |first7=Jacques |last8=Rietjens |first8=Ivonne M.C.M. |title=Mode of action based risk assessment of the botanical food-borne alkenylbenzene apiol from parsley using physiologically based kinetic (PBK) modelling and read-across from safrole |journal=Food and Chemical Toxicology |date=March 2016 |volume=89 |pages=138–150 |doi=10.1016/j.fct.2016.01.018 |pmid=26826679 |doi-access=free }}</ref> No carcinogenicity was detected with parsley apiol or dill apiol in mice.<ref>{{cite journal |last1=Randerath |first1=Kurt |last2=Haglund |first2=Roberta E. |last3=Phillips |first3=David H. |last4=Reddy |first4=M. Vijayaraj |title=³²P-Post-labelling analysis of DNA adducts formed in the livers of animals treated with safrole, estragole and other naturally-occurring alkenylbenzenes. I. Adult female CD-1 mice |journal=Carcinogenesis |date=1984 |volume=5 |issue=12 |pages=1613–1622 |doi=10.1093/carcin/5.12.1613 |pmid=6499112 }}</ref>

==Other similarly named compounds ==

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''.{{fact|date=September 2021}}

* [[Myristicin]]

{{reflist}}

== External links ==

* [http://www.chemindustry.com/apps/chemicals?m=d&i=169023 Apiol chemical information from chemindustry.com]{{Dead link|date=September 2023 |bot=InternetArchiveBot |fix-attempted=yes }}

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{{Phenylpropene}}

[[Category:Phenylpropenes]]

[[Category:O-methylated phenylpropanoids]]

[[Category:Allyl compounds]]