Apiole: Difference between revisions
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m Many references to apiol are to the extracted oleoresin. Work in progress! |
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| verifiedrevid = 444578066 |
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| Name = |
| Name = Apiole |
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| ImageFile = Apiol |
| ImageFile = Apiol structure.svg |
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| ImageAlt = Skeletal formula |
| ImageAlt = Skeletal formula |
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| ImageFile1 = Apiol-3D-balls.png |
| ImageFile1 = Apiol-3D-balls.png |
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| ImageAlt1 = Ball-and-stick model |
| ImageAlt1 = Ball-and-stick model |
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| PIN = 4,7-Dimethoxy-5-(prop-2-en-1-yl)-2''H''-1,3-benzodioxole |
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| IUPACName = 1-allyl-2,5-dimethoxy-<br />3,4-methylenedioxybenzene |
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| OtherNames = 5-Allyl-4,7-dimethoxybenzo[''d''][1,3]dioxole<br />1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene |
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|Section1={{Chembox Identifiers |
|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| KEGG = C10429 |
| KEGG = C10429 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = |
| ChEMBL = 1560118 |
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| 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 |
| 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 |
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| InChIKey = QQRSPHJOOXUALR-UHFFFAOYAO |
| InChIKey = QQRSPHJOOXUALR-UHFFFAOYAO |
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| UNII_Ref = {{fdacite|correct|FDA}} |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = QQ67504PXO |
| UNII = QQ67504PXO |
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| PubChem = 10659 |
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| EC_number = 208-349-2 |
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| ChEBI = 70353 |
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| SMILES = COc1cc(CC=C)c(OC)c2OCOc12 |
| SMILES = COc1cc(CC=C)c(OC)c2OCOc12 |
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'''Apiole''' is a [[phenylpropene]], also known as apiol, |
'''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]]. |
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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 |
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> |
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[[Hippocrates]] wrote about parsley as |
[[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. |
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==Orthography== |
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'''[[Apiol]]''', also known as 'liquid apiol' or 'green oil of [[parsley]]' is the extracted [[oleoresin]] of parsley, rather than the distilled oil. Due to its similarity to the term [[apiole]], care should be taken to avoid confusion. 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.<ref>{{cite news|author1=Phillips DH|author2=Reddy MV|author3=Randerath K|year=1984|title=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|journal=Carcinogenesis|volume=5|issue=12|pages=1623–8}}</ref> |
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'''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=<sup>32</sup>P-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> |
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==Other similarly named compounds == |
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Now that safer methods of abortion are available, apiol is almost forgotten. |
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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}} |
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The name apiole is also used for a closely related compound, found in [[dill]] ([[dillapiole]], 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene) and in [[fennel]] roots. |
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== See also == |
== See also == |
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* [[Dillapiole]] |
* [[Dillapiole]] |
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* [[ |
* [[Myristicin]] |
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==References== |
==References== |
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== External links == |
== External links == |
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* [http://www.chemindustry.com/apps/chemicals?m=d&i=169023 Apiol chemical information from chemindustry.com] |
* [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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* |
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* {{ChemID|523-80-8}} |
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{{Phenylpropene}} |
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* [http://toxnet.nlm.nih.gov/cgi-bin/sis/search/f?./temp/~GFOqCJ:7 Essential oil from fennel plants--studies on the composition] |
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[[Category:Phenylpropenes]] |
[[Category:Phenylpropenes]] |
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[[Category:O- |
[[Category:O-methylated phenylpropanoids]] |
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[[Category:Abortifacients]] |
[[Category:Abortifacients]] |
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[[Category: |
[[Category:Allyl compounds]] |
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[[Category:Benzodioxoles]] |
[[Category:Benzodioxoles]] |
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Latest revision as of 12:06, 30 December 2023
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| Names | |
|---|---|
| Preferred IUPAC name
4,7-Dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole | |
| Other names
5-Allyl-4,7-dimethoxybenzo[d][1,3]dioxole
1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene | |
| Identifiers | |
3D model (JSmol)
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.007.592 |
| EC Number |
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| KEGG | |
PubChem CID
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| UNII | |
CompTox Dashboard (EPA)
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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) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.[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 apiole have been reported.[4][5]
Hippocrates wrote about parsley as an herb to cause an abortion.[6] 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
[edit]Apiole (always with the final 'e') is the correct spelling[citation needed] of the trivial name for 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene.[7] 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.[8] No carcinogenicity was detected with parsley apiol or dill apiol in mice.[9]
Other similarly named compounds
[edit]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.[citation needed]
See also
[edit]References
[edit]- ^ 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.[page needed]
- ^ Amerio, A; De Benedictis, G; Leondeff, J; Mastrangelo, F; Coratelli, P (January 1968). "La nefropatia da apiolo" [Nephropathy due to apiol]. Minerva Nefrologica (in Italian). 15 (1): 49–70. OCLC 100396864. PMID 5736450.
- ^ Quinn, Louis J.; Harris, Cecil; Joron, Guy E. (15 April 1958). "Apiol Poisoning". Canadian Medical Association Journal. 78 (8): 635–636. PMC 1829842. PMID 20325694.
- ^ Hermann, Kate; Le Roux, Anne; Fiddes, F.S. (June 1956). "Death from apiol used as abortifacient". The Lancet. 267 (6929): 937–939. doi:10.1016/s0140-6736(56)91522-7. PMID 13320936.
- ^ Sage-Femme Collective (2008). Natural Liberty: Rediscovering Self-induced Abortion Methods. Natural Liberty. ISBN 978-0-9645920-0-1.[page needed]
- ^ Shulgin, Alexander T. (April 1966). "Possible Implication of Myristicin as a Psychotropic Substance" (PDF). Nature. 210 (5034): 380–384. Bibcode:1966Natur.210..380S. doi:10.1038/210380a0. PMID 5336379. S2CID 4189608.[failed verification]
- ^ Alajlouni, Abdalmajeed M.; Al_Malahmeh, Amer J.; Kiwamoto, Reiko; Wesseling, Sebastiaan; Soffers, Ans E.M.F.; Al-Subeihi, Ala A.A.; Vervoort, Jacques; Rietjens, Ivonne M.C.M. (March 2016). "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". Food and Chemical Toxicology. 89: 138–150. doi:10.1016/j.fct.2016.01.018. PMID 26826679.
- ^ Randerath, Kurt; Haglund, Roberta E.; Phillips, David H.; Reddy, M. Vijayaraj (1984). "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". Carcinogenesis. 5 (12): 1613–1622. doi:10.1093/carcin/5.12.1613. PMID 6499112.