1.0 2010-04-08 22:09:46 UTC 2025-11-18 23:30:06 UTC FDB011672 Safrole Occurs in nutmeg. Banned by FDA for use in food. Formerly used as a food flavour 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-allyl)benzene (Allyldioxy)benzene methylene ether (e)5-1-Propenyl]-1,3-benzodioxole 1-Allyl-3,4-methylenedioxybenzene 1-Allyl,3,4-methylenedioxy benzene 1, 2-(Methylenedioxy)-4-allylbenzene 1,2-(Methylenedioxy)-4-propenylbenzene 1,2-Methylenedioxy-4-allyl-benzene 1,2-Methylenedioxy-4-allylbenzene 3-(3,4-Methylenedioxyphenyl)prop-1-ene 3, 4-(Methylenedioxy)allylbenzene 3,4-(Methylenedioxy)-1-propenylbenzene 3,4-(Methylenedioxy)allylbenzene 3,4-Methylenedioxy-allybenzene 3,4-Methylenedioxyallylbenzene 4-Allyl-1, 2-(methylenedioxy)benzene 4-Allyl-1,2-(methylenedioxy)benzene, 8CI 4-Allyl-1,2-methylenedioxybenzene 4-Allylpyrocatechol 4-Allylpyrocatechol formaldehyde acetal 4-Propenyl-1,2-methylenedioxybenzene 4-Propenylcatechol methylene ether 5-(1-Propenyl)-1,3-benzodioxole 5-(2-Propenyl)-1,3-benzodioxole 5-(2-Propenyl)-1,3-benzodioxole, 9CI 5-Allyl-1,3-benzodioxolerlet DS Base 5-Allyl-benzo[1,3]dioxole 5-Prop-2-enyl-1,3-benzodioxole 6-(1-Propenyl)-1,3-benzodioxole Allylcatechol methylene ether Allyldioxybenzene methylene ether Allylpyrocatechol methylene ether Isosafrol Isosafrole Izosafrol m-Allylpyrocatechin methylene ether Safrol Shikimol Shikimole Shikomol C10H10O2 162.1852 162.068079564 5-(prop-2-en-1-yl)-2H-1,3-benzodioxole sassafras 94-59-7 C=CCC1=CC2=C(OCO2)C=C1 InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2 ZMQAAUBTXCXRIC-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 Benzenoids Hydrocarbon derivatives Oxacyclic compounds Acetal Aromatic heteropolycyclic compound Benzenoid Benzodioxole Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle benzodioxoles Liquid logp 2.23 ALOGPS logs -2.12 ALOGPS solubility 1.24e+00 g/l ALOGPS melting_point Fp 11.2° logp 2.7 ChemAxon pka_strongest_basic -4.7 ChemAxon iupac 5-(prop-2-en-1-yl)-2H-1,3-benzodioxole ChemAxon average_mass 162.1852 ChemAxon mono_mass 162.068079564 ChemAxon smiles C=CCC1=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/h2,4-6H,1,3,7H2 ChemAxon inchikey ZMQAAUBTXCXRIC-UHFFFAOYSA-N ChemAxon polar_surface_area 18.46 ChemAxon refractivity 46.11 ChemAxon polarizability 17.24 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 555 Specdb::NmrOneD 2713 Specdb::NmrOneD 3405 Specdb::CMs 26539 Specdb::CMs 28044 Specdb::CMs 29097 Specdb::CMs 29522 Specdb::CMs 29548 Specdb::CMs 29628 Specdb::CMs 101347 Specdb::CMs 101348 Specdb::CMs 101349 Specdb::CMs 101350 Specdb::CMs 101351 Specdb::CMs 151651 Specdb::MsIr 6174 Specdb::MsIr 6175 Specdb::MsMs 71928 Specdb::MsMs 71929 Specdb::MsMs 71930 Specdb::MsMs 130707 Specdb::MsMs 130708 Specdb::MsMs 130709 Specdb::MsMs 2686308 Specdb::MsMs 2686309 Specdb::MsMs 2686310 Specdb::MsMs 2992595 Specdb::MsMs 2992596 Specdb::MsMs 2992597 HMDB33591 #<Reference:0x000055ce2dd468d0> #<Reference:0x000055ce2dd44be8> #<Reference:0x000055ce2dd446e8> #<Reference:0x000055ce2dd44170> Anise Type 1 specific Pimpinella anisum 271192 Black tea Type 1 Ceylon cinnamon Type 1 specific Cinnamomum verum 128608 Chinese cinnamon Type 1 specific Cinnamomum aromaticum 119260 Dill Type 1 specific Anethum graveolens 40922 Green tea Type 1 Herbal tea Type 1 Herbs and Spices Unknown generic Nutmeg Type 1 specific Myristica fragrans 51089 142.0 142.0 142.0 mg/100 g Pepper (Spice) Type 1 specific Piper nigrum 13216 Red tea Type 1 Rosemary Type 1 specific Rosmarinus officinalis 39367 6.35 6.35 6.35 mg/100 g Star anise Type 1 specific Illicium verum 124778 Sweet basil Type 1 specific Ocimum basilicum 39350 23.0 23.0 23.0 mg/100 g Tamarind Type 1 specific Tamarindus indica 58860 Tea Type 1 specific Camellia sinensis 4442 anise floral sassafrass spice spicy sweet warm woody Anesthetic 62 Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti convulsant 204 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti septic 603 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-aggregant 94 Calcium antagonist 748 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. 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. Carminative 774 Central nervous system depressant 812 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. 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. Controlled 831 Cytochrome-p450 inducer 854 Cytochrome-p488 inducer 856 DNA-binder 886 Hepatocarcinogenic 978 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. Hepatoregenerative 982 Any compound that is able to prevent damage to the liver. Hepatotoxic 984 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals. Hypothermic 1023 Irritant 1055 Mutagenic 1125 Nematicide 1141 A substance used to destroy pests of the phylum Nematoda (roundworms). Neurotoxic 1160 A poison that interferes with the functions of the nervous system. Pediculicide 1202 Substance used to treat lice (genus Pediculus) infestation. Perfumery 1206 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. 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. Psychoactive 1268 A loosely defined grouping of drugs that have effects on psychological function. Tremorigenic 1376