Structure via PubChem · Public domain (PubChem)
apiole
Sign in to saveAlso known as apiol, 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene
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. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855, Joret and Homolle discovered that apiol was an effective treatment of amenorrhea (lack of menstruation).
Chemical data
- Formula
- C12H14O4
- Molecular weight
- 222.24 g/mol
- IUPAC name
- 4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole
- SMILES
- COC1=C2C(=C(C(=C1)CC=C)OC)OCO2
- InChIKey
- QQRSPHJOOXUALR-UHFFFAOYSA-N
- XLogP
- 2.7
- Polar surface area
- 36.9 Ų
- H-bond donors
- 0
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 222.089209
Show 3 more facts
- chemical formula
- C₁₂H₁₄O₄
- canonical SMILES
- COC1=C2C(=C(C(=C1)CC=C)OC)OCO2
- Commons category
- Apiol
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- Orthography
- Other similarly named compounds
- See also
- References
- External links
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. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855, Joret and Homolle discovered that apiol was an effective treatment of amenorrhea (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. Cases of death due to attempted abortion using apiole have been reported.
Excerpted from Wikipedia’s “apiole” article, available under the CC BY-SA 4.0 licence.