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Safrole (FDB011672)

Record Information
Version1.0
Creation date2010-04-08 22:09:46 UTC
Update date2019-11-26 03:05:14 UTC
Primary IDFDB011672
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameSafrole
DescriptionOccurs 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.
CAS Number94-59-7
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.24 g/LALOGPS
logP2.23ALOGPS
logP2.7ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area18.46 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity46.11 m³·mol⁻¹ChemAxon
Polarizability17.24 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H10O2
IUPAC name5-(prop-2-en-1-yl)-2H-1,3-benzodioxole
InChI IdentifierInChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2
InChI KeyZMQAAUBTXCXRIC-UHFFFAOYSA-N
Isomeric SMILESC=CCC1=CC2=C(OCO2)C=C1
Average Molecular Weight162.1852
Monoisotopic Molecular Weight162.068079564
Classification
Description 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzodioxoles
Sub ClassNot Available
Direct ParentBenzodioxoles
Alternative Parents
Substituents
  • Benzodioxole
  • Benzenoid
  • Oxacycle
  • Acetal
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Environmental role:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 74.06%; H 6.21%; O 19.73%DFC
Melting PointFp 11.2°DFC
Boiling PointBp6 104-105°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive Indexn20D 1.5383DFC
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0ik9-4900000000-9558c12b4c5a01a274902014-09-20View Spectrum
GC-MSSafrole, non-derivatized, GC-MS Spectrumsplash10-0ik9-3900000000-27e98ee529004a2d8b66Spectrum
GC-MSSafrole, non-derivatized, GC-MS Spectrumsplash10-0ik9-6900000000-54b4c1509456711936dfSpectrum
GC-MSSafrole, non-derivatized, GC-MS Spectrumsplash10-03di-6900000000-87b7efd770862a8f97a5Spectrum
GC-MSSafrole, non-derivatized, GC-MS Spectrumsplash10-0ik9-5900000000-0e7164aea8e5fa73ab55Spectrum
GC-MSSafrole, non-derivatized, GC-MS Spectrumsplash10-03di-0900000000-cae3268c72651c72100cSpectrum
GC-MSSafrole, non-derivatized, GC-MS Spectrumsplash10-0ik9-3900000000-27e98ee529004a2d8b66Spectrum
GC-MSSafrole, non-derivatized, GC-MS Spectrumsplash10-0ik9-6900000000-54b4c1509456711936dfSpectrum
GC-MSSafrole, non-derivatized, GC-MS Spectrumsplash10-03di-6900000000-87b7efd770862a8f97a5Spectrum
GC-MSSafrole, non-derivatized, GC-MS Spectrumsplash10-0ik9-5900000000-0e7164aea8e5fa73ab55Spectrum
GC-MSSafrole, non-derivatized, GC-MS Spectrumsplash10-03di-0900000000-cae3268c72651c72100cSpectrum
Predicted GC-MSSafrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01sa-2900000000-390702c1e607859e4700Spectrum
Predicted GC-MSSafrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-ce90b24b2ef83a6092612016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-cb602c608751e483efce2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9600000000-85407378b64267759f6d2016-08-02View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-f5650e9b49b023a3cfd22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-9dbd39032834251755462016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ti-5900000000-4204c0caaf5bb9b5d2582016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-9b0c6d7bc981d77b19272021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03k9-0900000000-01530378eccaf5c845f02021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fvr-9400000000-d251b0867c3f55c2e90e2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-4d3d221c51bdf4e740a22021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-3a92a79dc10e1183839f2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ot-7900000000-1024f7dba32bfc58ce372021-09-25View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
ChemSpider ID13848731
ChEMBL IDCHEMBL242273
KEGG Compound IDC10490
Pubchem Compound ID5144
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB33591
CRC / DFC (Dictionary of Food Compounds) IDGXV45-I:GXV45-I
EAFUS ID3354
Dr. Duke IDSAFROLE
BIGG IDNot Available
KNApSAcK IDC00002771
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID94-59-7
GoodScent IDrw1010791
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anestheticDUKE
anti aggregantDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti convulsant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
calcium antagonist48706 Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
carcinogenic50903 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.DUKE
carminativeDUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
central nervous system stimulant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
controlledDUKE
cytochrome-p450 inducerDUKE
cytochrome-p488 inducerDUKE
DNA-binderDUKE
hepatocarcinogenic50903 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.DUKE
hepatoregenerative62868 Any compound that is able to prevent damage to the liver.DUKE
hepatotoxic50908 A role played by a chemical compound exihibiting itself through the ability to induce damage to the liver in animals.DUKE
hypothermicDUKE
irritantDUKE
mutagenicDUKE
nematicide25491 A substance used to destroy pests of the phylum Nematoda (roundworms).DUKE
neurotoxic50910 A poison that interferes with the functions of the nervous system.DUKE
pediculicide38706 Substance used to treat lice (genus Pediculus) infestation.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
psychoactive35471 A loosely defined grouping of drugs that have effects on psychological function.DUKE
tremorigenicDUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
spice
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
warm
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sassafrass
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
anise
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.