1.0 2010-04-08 22:09:54 UTC 2019-11-26 03:05:45 UTC FDB011929 Apiole Occurs in Sassafras albidum (sassafras) and Anethum graveolens (dill) Apiol is an organic chemical compound, also known as parsley apiol, apiole or parsley camphor. It is found in celery, parsley seeds, and the essential oil 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 amenorrea or lack of menstruation.; In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders. It is an irritant and in high doses it is toxic and can cause liver and kidney damage. 1-Allyl-2,5-dimethoxy-3, 4-(methylenedioxy)benzene 1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)-benzene 1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)benzene 1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene 1,3-Benzodioxole, 4, 7-dimethoxy-5-(2-propenyl)- 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propen-1-yl)- 1,3-Benzodioxole, 4,7-dimethoxy-5-(2-propenyl)- 4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole 4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9CI 5-Allyl-4,7-dimethoxy-1,3-benzodioxol 5-Allyl-4,7-dimethoxy-1,3-benzodioxole Apiol Apiole (parsley) Apioline Benzene, 1-allyl-2,5-dimethoxy-3, 4-(methylenedioxy)- Benzene, 1-allyl-2,5-dimethoxy-3,4-(methylenedioxy)- Camphre de persil Parsley apiol Parsley apiole Parsley camphor Petersiliencampher C12H14O4 222.2372 222.089208936 4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole apiol 523-80-8 COC1=C2OCOC2=C(OC)C(CC=C)=C1 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 QQRSPHJOOXUALR-UHFFFAOYSA-N belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. Benzodioxoles Organic compounds Organoheterocyclic compounds Benzodioxoles Aromatic heteropolycyclic compounds Acetals Alkyl aryl ethers Anisoles Hydrocarbon derivatives Oxacyclic compounds Acetal Alkyl aryl ether Anisole Aromatic heteropolycyclic compound Benzenoid Benzodioxole Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle benzodioxoles logp 2.34 ALOGPS logs -2.55 ALOGPS solubility 6.33e-01 g/l ALOGPS melting_point Mp 30° logp 2.38 ChemAxon pka_strongest_basic -4.4 ChemAxon iupac 4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole ChemAxon average_mass 222.2372 ChemAxon mono_mass 222.089208936 ChemAxon smiles COC1=C2OCOC2=C(OC)C(CC=C)=C1 ChemAxon formula C12H14O4 ChemAxon inchi 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 ChemAxon inchikey QQRSPHJOOXUALR-UHFFFAOYSA-N ChemAxon polar_surface_area 36.92 ChemAxon refractivity 59.04 ChemAxon polarizability 22.87 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 4 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 1802 Specdb::CMs 20324 Specdb::CMs 132479 Specdb::CMs 140213 Specdb::MsMs 88464 Specdb::MsMs 88465 Specdb::MsMs 88466 Specdb::MsMs 151203 Specdb::MsMs 151204 Specdb::MsMs 151205 Specdb::MsMs 2698269 Specdb::MsMs 2698270 Specdb::MsMs 2698271 Specdb::MsMs 2984483 Specdb::MsMs 2984484 Specdb::MsMs 2984485 HMDB33776 #<Reference:0x000055ce316eb388> Black tea Type 1 Dill Type 1 specific Anethum graveolens 40922 Fennel Type 1 specific Foeniculum vulgare 48038 Green tea Type 1 Herbal tea Type 1 Herbs and Spices Unknown generic Lovage Type 1 specific Levisticum officinale 48042 Parsley Type 1 specific Petroselinum crispum 4043 1406.309 2811.5 1.118 mg/100 g Red tea Type 1 Tea Type 1 specific Camellia sinensis 4442 Wild celery Type 1 specific Apium graveolens 4045 faint parsley Abortifacient 13 A chemical substance that interrupts pregnancy after implantation. Anti dysmenorrheic 241 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti neuralgic 469 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti pyretic 567 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever. Anti-malarial 416 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-reproductive 575 Anti-spasmodic 619 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Calcium antagonist 748 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. Central nervous system stimulant 816 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. Diuretic 883 An agent that promotes the excretion of urine through its effects on kidney function. Emmenagogue 900 Hepatotoxic 984 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals. Insecticide 1040 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. Intoxicant 1053 A role played by the molecular entity or part thereof which causes the development of a pathological process. Irritant 1055 Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Secretolytic 1309 Synergist 1343 Utero tonic 1405 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Vasodilator 1413 A drug used to cause dilation of the blood vessels.