1.02010-04-08 22:09:46 UTC2019-11-26 03:05:14 UTCFDB011672SafroleOccurs 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-benzodioxole1-Allyl-3,4-methylenedioxybenzene1-Allyl,3,4-methylenedioxy benzene1, 2-(Methylenedioxy)-4-allylbenzene1,2-(Methylenedioxy)-4-propenylbenzene1,2-Methylenedioxy-4-allyl-benzene1,2-Methylenedioxy-4-allylbenzene3-(3,4-Methylenedioxyphenyl)prop-1-ene3, 4-(Methylenedioxy)allylbenzene3,4-(Methylenedioxy)-1-propenylbenzene3,4-(Methylenedioxy)allylbenzene3,4-Methylenedioxy-allybenzene3,4-Methylenedioxyallylbenzene4-Allyl-1, 2-(methylenedioxy)benzene4-Allyl-1,2-(methylenedioxy)benzene, 8CI4-Allyl-1,2-methylenedioxybenzene4-Allylpyrocatechol4-Allylpyrocatechol formaldehyde acetal4-Propenyl-1,2-methylenedioxybenzene4-Propenylcatechol methylene ether5-(1-Propenyl)-1,3-benzodioxole5-(2-Propenyl)-1,3-benzodioxole5-(2-Propenyl)-1,3-benzodioxole, 9CI5-Allyl-1,3-benzodioxolerlet DS Base5-Allyl-benzo[1,3]dioxole5-Prop-2-enyl-1,3-benzodioxole6-(1-Propenyl)-1,3-benzodioxoleAllylcatechol methylene etherAllyldioxybenzene methylene etherAllylpyrocatechol methylene etherIsosafrolIsosafroleIzosafrolm-Allylpyrocatechin methylene etherSafrolShikimolShikimoleShikomolC10H10O2162.1852162.0680795645-(prop-2-en-1-yl)-2H-1,3-benzodioxolesassafras94-59-7C=CCC1=CC2=C(OCO2)C=C1InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2ZMQAAUBTXCXRIC-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.BenzodioxolesOrganic compoundsOrganoheterocyclic compoundsBenzodioxolesAromatic heteropolycyclic compoundsAcetalsBenzenoidsHydrocarbon derivativesOxacyclic compoundsAcetalAromatic heteropolycyclic compoundBenzenoidBenzodioxoleHydrocarbon derivativeOrganic oxygen compoundOrganooxygen compoundOxacyclebenzodioxolesLiquidlogp2.23logs-2.12solubility1.24e+00 g/lmelting_pointFp 11.2°logp2.7pka_strongest_basic-4.7iupac5-(prop-2-en-1-yl)-2H-1,3-benzodioxoleaverage_mass162.1852mono_mass162.068079564smilesC=CCC1=CC2=C(OCO2)C=C1formulaC10H10O2inchiInChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2inchikeyZMQAAUBTXCXRIC-UHFFFAOYSA-Npolar_surface_area18.46refractivity46.11polarizability17.24rotatable_bond_count2acceptor_count2donor_count0physiological_charge0formal_charge0Specdb::EiMs555Specdb::NmrOneD2713Specdb::NmrOneD3405Specdb::MsIr6174Specdb::MsIr6175Specdb::CMs26539Specdb::CMs28044Specdb::CMs29097Specdb::CMs29522Specdb::CMs29548Specdb::CMs29628Specdb::CMs101347Specdb::CMs101348Specdb::CMs101349Specdb::CMs101350Specdb::CMs101351Specdb::CMs151651Specdb::MsMs71928Specdb::MsMs71929Specdb::MsMs71930Specdb::MsMs130707Specdb::MsMs130708Specdb::MsMs130709Specdb::MsMs2686308Specdb::MsMs2686309Specdb::MsMs2686310Specdb::MsMs2992595Specdb::MsMs2992596Specdb::MsMs2992597HMDB33591#<Reference:0x000055567644dd48>#<Reference:0x000055567644db90>#<Reference:0x000055567644d960>#<Reference:0x000055567644d758>AniseType 1specificPimpinella anisum271192Black teaType 1Ceylon cinnamonType 1specificCinnamomum verum128608Chinese cinnamonType 1specificCinnamomum aromaticum119260DillType 1specificAnethum graveolens40922Green teaType 1Herbal teaType 1Herbs and SpicesUnknowngenericNutmegType 1specificMyristica fragrans51089142.0142.0142.0mg/100 gPepper (Spice)Type 1specificPiper nigrum13216Red teaType 1RosemaryType 1specificRosmarinus officinalis393676.356.356.35mg/100 gStar aniseType 1specificIllicium verum124778Sweet basilType 1specificOcimum basilicum3935023.023.023.0mg/100 gTamarindType 1specificTamarindus indica58860TeaType 1specificCamellia sinensis4442anisefloralsassafrassspicespicysweetwarmwoodyanesthetic62anti aggregant94anti bacterial145A substance that kills or slows the growth of bacteria.anti convulsant204Any substance introduced into a living organism with therapeutic or diagnostic purpose.anti septic603A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.calcium antagonist748Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.cancer preventive754A substance that inhibits or prevents the proliferation of neoplasms.carcinogenic762A 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.carminative774central nervous system depressant812A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.central nervous system stimulant816A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.controlled831cytochrome-p450 inducer854cytochrome-p488 inducer856DNA-binder886hepatocarcinogenic978A 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.hepatoregenerative982Any compound that is able to prevent damage to the liver.hepatotoxic984A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.hypothermic1023irritant1055mutagenic1125nematicide1141A substance used to destroy pests of the phylum Nematoda (roundworms).neurotoxic1160A poison that interferes with the functions of the nervous system.pediculicide1202Substance used to treat lice (genus Pediculus) infestation.perfumery1206A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.pesticide1210Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.psychoactive1268A loosely defined grouping of drugs that have effects on psychological function.tremorigenic1376