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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:20:11 UTC
Update Date2019-07-23 06:13:49 UTC
HMDB IDHMDB0033591
Secondary Accession Numbers
  • HMDB0002333
  • HMDB02333
  • HMDB33591
Metabolite Identification
Common NameSafrole
DescriptionSafrole is found in anise. Safrole occurs in nutmeg. Banned by FDA for use in food. Safrole is 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. Safrole is 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
Structure
Data?1563862429
Synonyms
ValueSource
1,2-Methylenedioxy-4-allylbenzeneChEBI
1-Allyl-3,4-methylenedioxybenzeneChEBI
3,4-(Methylenedioxy)allylbenzeneChEBI
3-(3,4-Methylenedioxyphenyl)prop-1-eneChEBI
4-Allyl-1,2-methylenedioxybenzeneChEBI
4-Allylpyrocatechol formaldehyde acetalChEBI
5-(2-Propenyl)-1,3-benzodioxoleChEBI
5-Allyl-benzo[1,3]dioxoleChEBI
Allylcatechol methylene etherChEBI
m-Allylpyrocatechin methylene etherChEBI
SafrolChEBI
ShikimolChEBI
ShikimoleChEBI
(1,2-(Methylenedioxy)-4-allyl)benzeneHMDB
(Allyldioxy)benzene methylene etherHMDB
(e)5-1-Propenyl]-1,3-benzodioxoleHMDB
1, 2-(Methylenedioxy)-4-allylbenzeneHMDB
1,2-(Methylenedioxy)-4-propenylbenzeneHMDB
1,2-Methylenedioxy-4-allyl-benzeneHMDB
1-Allyl,3,4-methylenedioxy benzeneHMDB
3, 4-(Methylenedioxy)allylbenzeneHMDB
3,4-(Methylenedioxy)-1-propenylbenzeneHMDB
3,4-Methylenedioxy-allybenzeneHMDB
3,4-MethylenedioxyallylbenzeneHMDB
4-Allyl-1, 2-(methylenedioxy)benzeneHMDB
4-Allyl-1,2-(methylenedioxy)benzene, 8ciHMDB
4-AllylpyrocatecholHMDB
4-Propenyl-1,2-methylenedioxybenzeneHMDB
4-Propenylcatechol methylene etherHMDB
5-(1-Propenyl)-1,3-benzodioxoleHMDB
5-(2-Propenyl)-1,3-benzodioxole, 9ciHMDB
5-Allyl-1,3-benzodioxolerlet DS baseHMDB
5-Prop-2-enyl-1,3-benzodioxoleHMDB
6-(1-Propenyl)-1,3-benzodioxoleHMDB
Allyldioxybenzene methylene etherHMDB
Allylpyrocatechol methylene etherHMDB
IsosafrolHMDB
IsosafroleHMDB
IzosafrolHMDB
ShikomolHMDB
Chemical FormulaC10H10O2
Average Molecular Weight162.1852
Monoisotopic Molecular Weight162.068079564
IUPAC Name5-(prop-2-en-1-yl)-2H-1,3-benzodioxole
Traditional Namesassafras
CAS Registry Number94-59-7
SMILES
C=CCC1=CC2=C(OCO2)C=C1
InChI Identifier
InChI=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
Chemical Taxonomy
DescriptionThis compound 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
  • 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:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point11.2 °CNot Available
Boiling Point232–234 °CNot Available
Water SolubilityNot AvailableNot Available
LogPNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-3900000000-27e98ee529004a2d8b66JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-6900000000-54b4c1509456711936dfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-6900000000-87b7efd770862a8f97a5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-5900000000-0e7164aea8e5fa73ab55JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0900000000-cae3268c72651c72100cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-3900000000-27e98ee529004a2d8b66JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-6900000000-54b4c1509456711936dfJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-6900000000-87b7efd770862a8f97a5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0ik9-5900000000-0e7164aea8e5fa73ab55JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-0900000000-cae3268c72651c72100cJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01sa-2900000000-390702c1e607859e4700JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-ce90b24b2ef83a609261JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-1900000000-cb602c608751e483efceJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udl-9600000000-85407378b64267759f6dJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-f5650e9b49b023a3cfd2JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-9dbd3903283425175546JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02ti-5900000000-4204c0caaf5bb9b5d258JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-0ik9-4900000000-9558c12b4c5a01a27490JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011672
KNApSAcK IDC00002771
Chemspider ID13848731
KEGG Compound IDC10490
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkSafrole
METLIN IDNot Available
PubChem Compound5144
PDB IDNot Available
ChEBI ID8994
References
Synthesis ReferenceNguyen, Duc Tao; Le, Huyen; Pham, Van Tin. Study on the preparation of isosafrol from essential oil of Xa Xi. Tap Chi Duoc Hoc (1998), (1), 9-10.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Ioannides C, Lum PY, Parke DV: Cytochrome P-448 and the activation of toxic chemicals and carcinogens. Xenobiotica. 1984 Jan-Feb;14(1-2):119-37. [PubMed:6719936 ]
  2. Hung SL, Chen YL, Chen YT: Effects of safrole on the defensive functions of human neutrophils. J Periodontal Res. 2003 Apr;38(2):130-4. [PubMed:12608906 ]
  3. Zhao J, Miao J, Zhao B, Zhang S, Yin D: Safrole oxide inhibits angiogenesis by inducing apoptosis. Vascul Pharmacol. 2005 Jun;43(1):69-74. [PubMed:15936989 ]
  4. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .