1.0 2010-04-08 22:10:06 UTC 2026-09-18 19:00:37 UTC FDB012296 Isosafrole Isolated from leaves of the curryleaf (Murraya koenigii) and from star anise oil (Illicium religiosum) It is a precursor in the synthesis of the insecticide synergist piperonyl butoxide and the recreational drug MDMA ("Ecstacy."); Safrole is a natural plant constituent, found in oil of sassafras and certain other essential oils. It is a member of the methylenedioxybenzene group of compounds, many of which (e.g. piperonyl butoxide) are extensively used as insecticide synergists. A major source of human exposure to safrole is through consumption of spices, such as nutmeg, cinnamon and black pepper, in which safrole is a constituent. Safrole is also present in root beer, and has been used as an additive in chewing gum, toothpaste, soaps and certain pharmaceutical preparations. Safrole is a weak hepatocarcinogen and it is a matter of considerable interest whether the ally1 moiety or the methylenedioxy group, or both, are involved in the mechanism of its carcinogenesis. Safrole is extensively metabolized, giving rise to a large number of metabolites. Metabolism involves essentially two major routes, oxidation of the ally1 side chain, and oxidation of the methylenedioxy group with subsequent cleavage to form the catechol. Safrole undergoes oxidation of the allylic group to yield the 2, 3-epoxide (safrole epoxide). The dihydrodiol is one of the metabolites of safrole, and presumably arises from the hydration of the 2, 3-epoxide. The principal route of metabolism of safrole is through cleavage of the methylenedioxy group, the major metabolites being allylcatechol and its isomer, propenylcatechol. Eugenol and its isomer I-methoxy- 2-hydroxy-4-allylbenzene have been detected as minor metabolites in the rat, mouse and man. (PMID: 6719936); Safrole, also known as shikimol, is a colorless or slightly yellow oily liquid. It is typically extracted from the root-bark or the fruit of sassafras plants in the form of sassafras oil, or synthesized from other related methylenedioxy compounds. It is the principal component of brown camphor oil, and is found in small amounts in a wide variety of plants, where it functions as a natural pesticide. The Ocotea cymbarum[verification needed] oil made of the Ocotea pretiosa[verification needed], a plant growing in Brazil, and sassafras oil made of Sassafras albidum, a tree growing in eastern North America, are the main natural sources for safrole. It has a characteristic "candy-shop" aroma. 1, 2-(Methylenedioxy)-4-propenylbenzene 1,2-(Methylenedioxy)-4-(1-propenyl)benzene, 8CI 1,3-Benzodioxole, 5-(1-propenyl)- 3,4-Methylenedihydroxy-1-propenylbenzene 5-(1-Propenyl)-1,3-benzodioxole, 9CI 5-[(1E)-1-Propenyl]-1,3-benzodioxole Benzene, 1,2-(methylenedioxy)-4-propenyl- Safrole C10H10O2 162.1852 162.068079564 5-[(1Z)-prop-1-en-1-yl]-2H-1,3-benzodioxole 5-[(1Z)-prop-1-en-1-yl]-2H-1,3-benzodioxole 94-59-7 C\C=C/C1=CC2=C(OCO2)C=C1 InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2- VHVOLFRBFDOUSH-IHWYPQMZSA-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 Hydrocarbon derivatives Oxacyclic compounds Styrenes Acetal Aromatic heteropolycyclic compound Benzenoid Benzodioxole Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Styrene Liquid logp 2.92 ALOGPS logs -2.23 ALOGPS solubility 9.57e-01 g/l ALOGPS melting_point 6.75 oC logp 2.72 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 5-[(1Z)-prop-1-en-1-yl]-2H-1,3-benzodioxole ChemAxon average_mass 162.1852 ChemAxon mono_mass 162.068079564 ChemAxon smiles C\C=C/C1=CC2=C(OCO2)C=C1 ChemAxon formula C10H10O2 ChemAxon inchi InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2-6H,7H2,1H3/b3-2- ChemAxon inchikey VHVOLFRBFDOUSH-IHWYPQMZSA-N ChemAxon polar_surface_area 18.46 ChemAxon refractivity 47.18 ChemAxon polarizability 17.47 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 1224655 Specdb::MsMs 1224656 Specdb::MsMs 1224657 Specdb::MsMs 1340260 Specdb::MsMs 1340261 Specdb::MsMs 1340262 HMDB33591 #<Reference:0x00007f286c2481c8> #<Reference:0x00007f286c1dbd70> #<Reference:0x00007f286c1db898> #<Reference:0x00007f286c1db280> Herbs and Spices Unknown generic spice sweet warm Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti-Zika virus 1441 Carcinogenic 762 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. Genotoxic 950 A role played by a chemical compound to induce direct or indirect DNA damage. Such damage can potentially lead to the formation of a malignant tumour, but DNA damage does not lead inevitably to the creation of cancerous cells. Inhibitor 1432 A substance that diminishes the rate of a chemical reaction. 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. Nf-Kb-Inducer 1991 Toxic 1371 A role played by the molecular entity or part thereof which causes the development of a pathological process.