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=CC(CC=C)=C(OC)C2=C1OCO2
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 |
|---|---|---|
| Essential oil composition of sea fennel (Crithmum maritimum) form Turkey. | 2001 Oct |
|
| Enzyme activity in the flesh fly Parasarcophaga dux Thomson influenced by dill compounds, myristicin and apiol. | 2004 Apr |
|
| Toxicological efficacy of some indigenous dill compounds against the flesh fly, Parasarcophaga dux Thomson. | 2004 Apr |
|
| Evaluation of the efficacy of dill apiol and pyriproxyfen in the treatment and control of Xenopsylla cheopis flea Roths (Siphonaptera: Pulicidae). | 2005 Dec |
|
| Phytotoxic and antifungal compounds from two Apiaceae species, Lomatium californicum and Ligusticum hultenii, rich sources of Z-ligustilide and apiol, respectively. | 2005 Jul |
|
| Essential oil composition and antimicrobial activity of Diplotaenia damavandica. | 2005 Nov-Dec |
|
| Plant-derived natural products exhibiting activity against formosan subterranean termites (Coptotermes formosanus). | 2006 Jun |
|
| Dillapiol and Apiol as specific inhibitors of the biosynthesis of aflatoxin G1 in Aspergillus parasiticus. | 2007 Sep |
|
| A synthetic derivative of plant allylpolyalkoxybenzenes induces selective loss of motile cilia in sea urchin embryos. | 2008 Feb 15 |
|
| Antifungal activity of extracts of some plants used in Brazilian traditional medicine against the pathogenic fungus Paracoccidioides brasiliensis. | 2010 Apr |
|
| Natural toxins for use in pest management. | 2010 Aug |
|
| Acaricidal activity and chemical composition of the essential oil from three Piper species. | 2010 Jun |
|
| Free radical scavenging activities of Cnidium officinale Makino and Ligusticum chuanxiong Hort. methanolic extracts. | 2010 Oct |
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
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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admin
on
Edited
Fri Dec 15 15:00:45 UTC 2023
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Fri Dec 15 15:00:45 UTC 2023
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| Record UNII |
QQ67504PXO
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| Record Status |
Validated (UNII)
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APIOL
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208-349-2
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SUB75278
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C446539
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m1991
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