Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C12H14O4 |
| Molecular Weight | 222.2372 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2OCOC2=C(OC)C(CC=C)=C1
InChI
InChIKey=QQRSPHJOOXUALR-UHFFFAOYSA-N
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
| Molecular Formula | C12H14O4 |
| Molecular Weight | 222.2372 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Apiole (1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene) is a phenylpropene, also known as apiol, parsley apiol or parsley camphor, found in the essential oils of celery leaf and all parts of parsley. Apiole and various preparations of parsley have been used for many years to procure the illegal abortion in Italy. Post-abortive vaginal bleeding, sometimes profuse, is a feature of these cases. A cumulative effect is apparent, parsley apiole being taken daily for between two and eight days before either death or abortion ensued. The lowest daily dose of apiole which induced abortion was 0.9 g taken for eight consecutive days. Parsley apiole is toxic in humans; the lowest total dose of apiole causing death is 4.2 g (2.1 g/day for 2 days) the lowest fatal daily dose is 770 mg, which was taken for 14 days; the lowest single fatal dose is 8 g.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Free radical scavenging activities of Cnidium officinale Makino and Ligusticum chuanxiong Hort. methanolic extracts. | 2010-10 |
|
| Natural toxins for use in pest management. | 2010-08 |
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| Acaricidal activity and chemical composition of the essential oil from three Piper species. | 2010-06 |
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| Antifungal activity of extracts of some plants used in Brazilian traditional medicine against the pathogenic fungus Paracoccidioides brasiliensis. | 2010-04 |
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| A synthetic derivative of plant allylpolyalkoxybenzenes induces selective loss of motile cilia in sea urchin embryos. | 2008-02-15 |
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| Dillapiol and Apiol as specific inhibitors of the biosynthesis of aflatoxin G1 in Aspergillus parasiticus. | 2007-09 |
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| Plant-derived natural products exhibiting activity against formosan subterranean termites (Coptotermes formosanus). | 2006-06 |
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| Essential oil composition and antimicrobial activity of Diplotaenia damavandica. | 2006-01-13 |
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| Evaluation of the efficacy of dill apiol and pyriproxyfen in the treatment and control of Xenopsylla cheopis flea Roths (Siphonaptera: Pulicidae). | 2005-12 |
|
| Phytotoxic and antifungal compounds from two Apiaceae species, Lomatium californicum and Ligusticum hultenii, rich sources of Z-ligustilide and apiol, respectively. | 2005-07 |
|
| Enzyme activity in the flesh fly Parasarcophaga dux Thomson influenced by dill compounds, myristicin and apiol. | 2004-04 |
|
| Toxicological efficacy of some indigenous dill compounds against the flesh fly, Parasarcophaga dux Thomson. | 2004-04 |
|
| Essential oil composition of sea fennel (Crithmum maritimum) form Turkey. | 2001-10 |
Patents
Sample Use Guides
Daily oral maximum for parsley apiole of 0.4 mg/kg. The lowest daily dose of apiole which induced abortion was 0.9 g taken for eight consecutive days
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21785624
The COLO 205 (p53 wild-type) cell line were used for activity evaluation. The anti-proliferative effects of the compounds on cultured cells were measured using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. The cells were seeded at a density of 2 x 10^4 cells per well in 24-well culture plates overnight and then treated with various concentrations of the compounds. After 24, 48 and 72 hours of incubation, 30 μL of 2 mg/mL MTT solution (in phosphate buffered saline (PBS), pH 7.4) was added to each well, and the plate was incubated for another 3 hours. Following incubation, the culture medium was removed from the wells by slow aspiration and replaced with 200 μl DMSO. The absorbance of each well was measured using an enzyme-linked immunosorbent assay (ELISA) reader at 550 nm.
| Substance Class |
Chemical
Created
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Edited
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QQ67504PXO
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