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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 18:20:11 UTC
Update Date2021-10-13 06:33:57 UTC
HMDB IDHMDB0033591
Secondary Accession Numbers
  • HMDB0002333
  • HMDB02333
  • HMDB33591
Metabolite Identification
Common NameSafrole
DescriptionSafrole, 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. Safrole is found in anise and 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 rat, mouse and human (PMID:6719936 ). The Ocotea cymbarum oil made of the Ocotea pretiosa, 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
4 Allyl 1,2 methylenedioxybenzeneMeSH
4-Allyl-1,2-methylenedioxybenzenesMeSH
SafrolesMeSH
ShikimolsMeSH
SafrolsMeSH
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
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

Biological location

Source

Route of exposure

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point11.2 °CNot Available
Boiling Point232–234 °CNot Available
Water Solubility1.08 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available138.573http://allccs.zhulab.cn/database/detail?ID=AllCCS00001146
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.24 g/LALOGPS
logP10(2.23) g/LALOGPS
logP10(2.7) g/LChemAxon
logS10(-2.1) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.60631661259
DarkChem[M-H]-132.93131661259
DeepCCS[M+H]+133.90430932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SafroleC=CCC1=CC2=C(OCO2)C=C11832.9Standard polar33892256
SafroleC=CCC1=CC2=C(OCO2)C=C11314.0Standard non polar33892256
SafroleC=CCC1=CC2=C(OCO2)C=C11295.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Safrole EI-B (Non-derivatized)splash10-0ik9-3900000000-27e98ee529004a2d8b662017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Safrole EI-B (Non-derivatized)splash10-0ik9-6900000000-54b4c1509456711936df2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Safrole EI-B (Non-derivatized)splash10-03di-6900000000-87b7efd770862a8f97a52017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Safrole EI-B (Non-derivatized)splash10-0ik9-5900000000-0e7164aea8e5fa73ab552017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Safrole EI-B (Non-derivatized)splash10-03di-0900000000-cae3268c72651c72100c2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Safrole EI-B (Non-derivatized)splash10-0ik9-3900000000-27e98ee529004a2d8b662018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Safrole EI-B (Non-derivatized)splash10-0ik9-6900000000-54b4c1509456711936df2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Safrole EI-B (Non-derivatized)splash10-03di-6900000000-87b7efd770862a8f97a52018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Safrole EI-B (Non-derivatized)splash10-0ik9-5900000000-0e7164aea8e5fa73ab552018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Safrole EI-B (Non-derivatized)splash10-03di-0900000000-cae3268c72651c72100c2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Safrole GC-MS (Non-derivatized) - 70eV, Positivesplash10-01sa-2900000000-390702c1e607859e47002017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Safrole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0ik9-4900000000-9558c12b4c5a01a274902014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 10V, Positive-QTOFsplash10-03di-0900000000-ce90b24b2ef83a6092612016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 20V, Positive-QTOFsplash10-03di-1900000000-cb602c608751e483efce2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 40V, Positive-QTOFsplash10-0udl-9600000000-85407378b64267759f6d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 10V, Negative-QTOFsplash10-03di-0900000000-f5650e9b49b023a3cfd22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 20V, Negative-QTOFsplash10-03di-0900000000-9dbd39032834251755462016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 40V, Negative-QTOFsplash10-02ti-5900000000-4204c0caaf5bb9b5d2582016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 10V, Positive-QTOFsplash10-03di-0900000000-9b0c6d7bc981d77b19272021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 20V, Positive-QTOFsplash10-03k9-0900000000-01530378eccaf5c845f02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 40V, Positive-QTOFsplash10-0fvr-9400000000-d251b0867c3f55c2e90e2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 10V, Negative-QTOFsplash10-03di-0900000000-4d3d221c51bdf4e740a22021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 20V, Negative-QTOFsplash10-03di-0900000000-3a92a79dc10e1183839f2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safrole 40V, Negative-QTOFsplash10-01ot-7900000000-1024f7dba32bfc58ce372021-09-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1619951
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.. .