Apiole

Apiole
Skeletal formula
Ball-and-stick model
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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.592
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EC Number
  • 208-349-2
KEGG
PubChem CID
UNII
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 checkY
    Key: QQRSPHJOOXUALR-UHFFFAOYSA-N checkY
  • 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).
☒N verify (what is checkY☒N ?)
Infobox references

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.

According to a book called PIHKAL, Apiole had been used to synthesize a psychedelic amphetamine called DMMDA.

Apiol or apiole?

Apiole (always with the final 'e') is the correct spelling 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 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. 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

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.

See also

References

  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; 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.
  4. ↑ 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.
  5. ↑ 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.
  6. ↑ Sage-Femme Collective (2008). Natural Liberty: Rediscovering Self-induced Abortion Methods. Natural Liberty. ISBN 978-0-9645920-0-1.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ 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.
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