Apiole

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Apiole

Apiole is a naturally occurring organic compound found in various plants, most notably in parsley (Petroselinum crispum) and dill (Anethum graveolens). It is a phenylpropene, a type of phenylpropanoid that is related to myristicin and safrole. Apiole has been studied for its potential medicinal properties and its historical use in herbal medicine.

Chemical Structure and Properties

Apiole is classified as a phenylpropene, with the chemical formula C12H14O4. It is a colorless to pale yellow liquid at room temperature. The compound is characterized by a methoxyphenyl group attached to a propenyl chain. Apiole is known for its distinctive aroma, which contributes to the characteristic scent of parsley and dill.

Sources

Apiole is primarily extracted from the seeds and leaves of parsley and dill. The compound is present in higher concentrations in the seeds compared to the leaves. Other plants that contain apiole include celery and fennel.

Historical Uses

Historically, apiole has been used in traditional medicine for its purported health benefits. In the 19th and early 20th centuries, it was used as an emmenagogue, a substance that stimulates menstrual flow. Apiole was also used in the form of "apiol oil" or "liquid apiol" as a remedy for menstrual disorders.

Pharmacology

Apiole has been studied for its potential pharmacological effects. It is known to have mild antimicrobial properties and has been investigated for its effects on the central nervous system. However, the use of apiole in modern medicine is limited due to its potential toxicity at high doses.

Toxicity

While apiole has been used historically for medicinal purposes, it can be toxic if consumed in large quantities. Symptoms of apiole toxicity include nausea, vomiting, dizziness, and headache. In severe cases, it can lead to liver and kidney damage. Therefore, caution is advised when using apiole-containing products.

Related Pages



Organic compounds
General
By element
Polymers
Biomolecules
Related
This organic compounds related article is a stub.



Types of phytochemicals
Terpenoids
Types of terpenes and terpenoids (# of isoprene units)
Basic forms:
* Acyclic (linear, cis and trans forms)
  • Monocyclic (single ring)
  • Bicyclic (2 rings)
  • Iridoids (cyclopentane ring)
  • Iridoid glycosides (iridoids bound to a sugar)
  • Steroids (4 rings)
Hemiterpenoids (1)
Monoterpenes (C10H16)(2)
Monoterpenoids (2,modified)
Sesquiterpenoids (3)
Phenolic compounds
Types of phenolic compounds
Natural monophenols
Polyphenols
Types of polyphenols
Flavonoids
(C6-C3-C6)
Flavonolignans
Lignans
((C6-C3)2)
Stilbenoids
(C6-C2-C6)
Curcuminoids
Aromatic acids
Aromatic acids
Phenolic acids
Hydroxycinnamic acids
Aromatic amino acids


Phenylethanoids
Others
Glucosinolates
Betalains
Chlorophylls
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Contributors: Prab R. Tumpati, MD