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Apiole (parsley)

1-(2-Propenyl)-2,5-dimethoxy-3,4-methylenedioxybenzene

Parsley apiol · Parsley camphor · Apioline

Bicyclic phenylpropenoid ether · C₁₂H₁₄O₄

Chemical structure of Apiole (parsley)
2D structure PubChem / NCI CIR

Chemical info

CAS number CAS
523-80-8
Molecular formula
C₁₂H₁₄O₄
Molecular weight
222.24 g/mol
Aroma
Pronounced parsley, spicy, warm, with camphoraceous undertones.

Safety

Hepatotoxic · Abortifacient · Severely restricted

Parsley apiole is hepatotoxic, nephrotoxic and cardiotoxic at high doses. Historically used to induce illegal abortion, the compound has a record of fatal poisoning in humans.

Oral. The lowest fatal cumulative dose in adults is 4.2 g (2.1 g/day for two days). The lowest single fatal dose is 8 g. Poisoning symptoms include fever, severe abdominal pain, vaginal bleeding, vomiting and diarrhea. Autopsies typically show severe damage to liver, kidneys, gastrointestinal tract and sometimes heart tissue.

Reproductive. The lowest abortifacient daily dose is 900 mg over eight consecutive days. In a five-case series of women 2–7 months pregnant, one aborted and died, one did not abort but died, three aborted and survived. The compound has a cumulative effect.

Liver. A single oral 10 mL/kg dose killed all 12 mice within 60 hours, with gross and microscopic damage to liver and kidney.

Human toxicity is estimated to be similar to pulegone. Recommended daily oral maximum is 0.4 mg/kg, equivalent to 28 mg for an adult, corresponding to a maximum dermal level of 0.76 percent.


Usage guidelines

Pregnancy
Absolutely contraindicated
Adult daily oral maximum
0.4 mg/kg · about 28 mg/adult
Maximum dermal level
0.76 percent
Oils with high content
Parsley seed 11.3–67.5 percent

Found in essential oils

Principal sources
Parsley seed11.3 – 67.5 %

Pharmacokinetics

Parsley apiole metabolism involves extensive oxidation in both rabbits and dogs. In one poisoning case, apiole was still detectable in urine 12 days after the last ingestion, indicating slow elimination.


Notes

Parsley apiole is decomposition-sensitive in storage. The compound binds DNA only weakly and is not associated with tumor development.

Animal toxicity is far lower than human toxicity, highlighting the limits of rodent-to-human extrapolation in this case.