Compound: Apiole
SMILES: O1c2c(OC)c(cc(c2OC1)OC)CC=C
InChIKey: QQRSPHJOOXUALR-UHFFFAOYSA-N
Synonyms: Apiole, Apioline, Apiol, 523-80-8, Apiole (parsley), 5-Allyl-4,7-dimethoxy-1,3-benzodioxole, 1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene, APIOLUM, QQ67504PXO, 4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole, NSC-9070, DTXSID4041236, 4,7-dimethoxy-5-prop-2-enyl-1,3-benzodioxole, 4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-Benzodioxole, RefChem:57677, Apiol 1503, DTXCID2021236, 208-349-2, Parsley apiole, Parsley camphor, Parsley apiol, Petersiliencampher, 5-Allyl-4,7-dimethoxybenzo[d][1,3]dioxole, 4,7-DIMETHOXY-5-(2-PROPANYL)-1,3-BENZODIOXOLE, 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propenyl)-, 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, NSC9070, NSC 9070, 5-Allyl-4,7-dimethoxy-1,3-benzodioxol, 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propen-1-yl)-, MFCD00047270, BENZENE, 1-ALLYL-2,5-DIMETHOXY-3,4-(METHYLENEDIOXY)-, WLN: T56 BO DO CHJ FO1 H2U1 IO1, 1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)benzene, 4,7-dimethoxy-5-prop-2-enyl-2H-benzo[d]1,3-dioxolene, Camphre de Persil, EINECS 208-349-2, BRN 0195747, APIOLE, PARSLEY, Spectrum_000400, APIOLE [VANDF], APIOLUM [HPUS], AI3-14843, Spectrum2_000419, Spectrum3_001283, Spectrum4_001643, Spectrum5_001718, UNII-QQ67504PXO, BSPBio_002885, KBioGR_002105, KBioSS_000880, SPECTRUM390001, SCHEMBL497412, SPBio_000378, orb1705655, APIOLE (PARSLEY) [MI], CHEMBL1560118, SCHEMBL29410305, CHEBI:70353, KBio2_000880, KBio2_003448, KBio2_006016, KBio3_002105, CCG-39582, MSK179657, SBB014761, STK664284, 1-Allyl-2,4-(methylenedioxy)benzene, AKOS003398564, 1, 4,7-dimethoxy-5-(2-propenyl)-, ApiolineApiole (parsley); Parsley apiole, NCGC00094551-01, NCGC00094551-02, NCGC00094551-03, FS-10667, ST097617, 5-allyl-4,7-dimethoxy-benzo-1,3-dioxole, Benzene,5-dimethoxy-3,4-(methylenedioxy)-, DB-052116, HY-135217, 5-Allyl-4,7-dimethoxy-1,3-benzodioxole #, CS-0109902, NS00032497, G88932, Apioline; Apiol; Parsley apiole; Parsley camphor, SR-05000002460, SR-05000002460-1, 1,3-benzodioxole, 4,7-dimethoxy-5-(2-propen-1-yl), 1-Allyl-2,5-dimethoxy-3, 4-(methylenedioxy)benzene, 1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)-Benzene, 4,7-dimethoxy-5-(prop-2-en-1-yl)-1,3-benzodioxole, Q21071561, 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9CI, 1,3-Benzodioxole,4,7-dimethoxy-5-(2-propenyl)- (9CI)
Theoretical properties:
molecular_formula: C12H14O4
molecular_weight: 222.24 g/mol
exact_mass: 222.08920892 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 4
heavy_atom_count: 16
topological_polar_surface_area: 36.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
boiling_point: 294.00 to 295.00 °C. @ 760.00 mm Hg
melting_point: 30 °C
density: 1.124-1.135
solubility: Insoluble in water; soluble in ether, acetone and glacial acetic acid
Descriptions:
pubchem: Apiole is a member of benzodioxoles. It has a role as a metabolite.
chembl: APIOL is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.
wikipedia: Apiole is a phenylpropene, also known as apiol, parsley apiol, or parsley camphor. Its chemical name is 1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene. It is found in the essential oils of celery leaf and all parts of parsley. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855, Joret and Homolle discovered that apiol was an effective treatment of amenorrhea (lack of menstruation).
In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders and as an abortifacient. It is an irritant and, in high doses, it can cause liver and kidney damage. Cases of death due to attempted abortion using apiole have been reported.
Hippocrates wrote about parsley as an herb to cause an abortion. Plants containing apiole were used by women in the Middle Ages to terminate pregnancies.  Now that safer methods of abortion are available, apiol is almost forgotten.