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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
Structure of APIOLE (PARSLEY)

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

HIDE SMILES / InChI
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.

Originator

Sources: Shorter, Edward (1991). Women's Bodies: A Social History of Women's Encounter With Health, Ill-Health, and Medicine. New Brunswick, NJ: Transaction Publishers.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
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

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.
Name Type Language
APIOLE (PARSLEY)
MI  
Common Name English
APIOLE [VANDF]
Common Name English
APIOLE (PARSLEY) [MI]
Common Name English
APIOLUM
HPUS  
Common Name English
NSC-9070
Code English
APIOLE
VANDF  
Common Name English
APIOL
Common Name English
APIOLINE
Common Name English
APIOLE, PARSLEY
Common Name English
APIOLUM [HPUS]
Common Name English
1-ALLYL-2,5-DIMETHOXY-3,4-METHYLENEDIOXYBENZENE
Systematic Name English
4,7-DIMETHOXY-5-(2-PROPENYL)-1,3-BENZODIOXOLE
Systematic Name English
Code System Code Type Description
JECFA MONOGRAPH
1765
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
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WIKIPEDIA
APIOL
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
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RXCUI
314506
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
PRIMARY RxNorm
ECHA (EC/EINECS)
208-349-2
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
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EVMPD
SUB75278
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
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MESH
C446539
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
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FDA UNII
QQ67504PXO
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
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EPA CompTox
DTXSID4041236
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
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PUBCHEM
10659
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
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SMS_ID
100000137080
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
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MERCK INDEX
m1991
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
PRIMARY Merck Index
CAS
523-80-8
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
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DAILYMED
QQ67504PXO
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
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NSC
9070
Created by admin on Fri Dec 15 15:00:46 GMT 2023 , Edited by admin on Fri Dec 15 15:00:46 GMT 2023
PRIMARY