NP-MRD: Showing NP-Card for Safrole (NP0000030)

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Record Information

Version

2.0

Created at

2012-09-11 18:20:11 UTC

Updated at

2025-02-11 15:46:02 UTC

NP-MRD ID

NP0000030

Natural Product DOI

https://doi.org/10.57994/0470

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Safrole

Description

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. 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

MOL SDF PDB SMILES InChI

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Safrole                                           
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  O   UNK     0       5.118   1.239   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0       5.118  -1.239   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.243   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.576   0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.576  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.909   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.577   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.243  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.909  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.220   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.911   0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.245   1.540   0.000  0.00  0.00           C+0
CONECT    1    4   10                                                       
CONECT    2    5   10                                                       
CONECT    3    6    7    8                                                  
CONECT    4    1    5    6                                                  
CONECT    5    2    4    9                                                  
CONECT    6    3    4                                                       
CONECT    7    3   11                                                       
CONECT    8    3    9                                                       
CONECT    9    5    8                                                       
CONECT   10    1    2                                                       
CONECT   11    7   12                                                       
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

View in JSmol

Synonyms

Value	Source
1,2-Methylenedioxy-4-allylbenzene	ChEBI
1-Allyl-3,4-methylenedioxybenzene	ChEBI
3,4-(Methylenedioxy)allylbenzene	ChEBI
3-(3,4-Methylenedioxyphenyl)prop-1-ene	ChEBI
4-Allyl-1,2-methylenedioxybenzene	ChEBI
4-Allylpyrocatechol formaldehyde acetal	ChEBI
5-(2-Propenyl)-1,3-benzodioxole	ChEBI
5-Allyl-benzo[1,3]dioxole	ChEBI
Allylcatechol methylene ether	ChEBI
m-Allylpyrocatechin methylene ether	ChEBI
Safrol	ChEBI
Shikimol	ChEBI
Shikimole	ChEBI
(1,2-(Methylenedioxy)-4-allyl)benzene	HMDB
(Allyldioxy)benzene methylene ether	HMDB
(e)5-1-Propenyl]-1,3-benzodioxole	HMDB
1, 2-(Methylenedioxy)-4-allylbenzene	HMDB
1,2-(Methylenedioxy)-4-propenylbenzene	HMDB
1,2-Methylenedioxy-4-allyl-benzene	HMDB
1-Allyl,3,4-methylenedioxy benzene	HMDB
3, 4-(Methylenedioxy)allylbenzene	HMDB
3,4-(Methylenedioxy)-1-propenylbenzene	HMDB
3,4-Methylenedioxy-allybenzene	HMDB
3,4-Methylenedioxyallylbenzene	HMDB
4-Allyl-1, 2-(methylenedioxy)benzene	HMDB
4-Allyl-1,2-(methylenedioxy)benzene, 8ci	HMDB
4-Allylpyrocatechol	HMDB
4-Propenyl-1,2-methylenedioxybenzene	HMDB
4-Propenylcatechol methylene ether	HMDB
5-(1-Propenyl)-1,3-benzodioxole	HMDB
5-(2-Propenyl)-1,3-benzodioxole, 9ci	HMDB
5-Allyl-1,3-benzodioxolerlet DS base	HMDB
5-Prop-2-enyl-1,3-benzodioxole	HMDB
6-(1-Propenyl)-1,3-benzodioxole	HMDB
Allyldioxybenzene methylene ether	HMDB
Allylpyrocatechol methylene ether	HMDB
Isosafrol	HMDB
Isosafrole	HMDB
Izosafrol	HMDB
Shikomol	HMDB
4 Allyl 1,2 methylenedioxybenzene	MeSH
4-Allyl-1,2-methylenedioxybenzenes	MeSH
Safroles	MeSH
Shikimols	MeSH
Safrols	MeSH

Chemical Formula

C₁₀H₁₀O₂

Average Mass

162.1852 Da

Monoisotopic Mass

162.06808 Da

IUPAC Name

5-(prop-2-en-1-yl)-2H-1,3-benzodioxole

Traditional Name

sassafras

CAS Registry Number

94-59-7

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 Key

ZMQAAUBTXCXRIC-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D_DEPT NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D_DEPT NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl3, experimental)	shaolidong@ynutcm.edu.cn	Not Available	Not Available	2024-05-11	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500.33, CDCl₃, simulated)	Not Available	Not Available	Not Available	2024-05-11	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Acorus gramineus		LOTUS database
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Angelica sinensis		LOTUS database
Aniba spp.	Plant	KNApSAcK
Apis cerana		LOTUS database
Asarum fauriei		LOTUS database
Asarum forbesii	Plant	KNApSAcK
Asarum heterotropoides		LOTUS database
Asarum heterotropoides var.mandshuricum	Plant	KNApSAcK
Asarum hypogynum		LOTUS database
Asarum kiusianum		LOTUS database
Asarum sieboldii	Plant	KNApSAcK
Asarum trigynum		LOTUS database
Atherosperma moschatum		LOTUS database
Averrhoa carambola	Plant	KNApSAcK
Baccharis dracunculifolia		LOTUS database
Boronia latipinna		LOTUS database
Cananga odorata		LOTUS database
Cinnamomum aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cinnamomum burmanni		LOTUS database
Cinnamomum camphora	Plant	KNApSAcK
Cinnamomum oliveri		LOTUS database
Cinnamomum parthenoxylon		LOTUS database
Cinnamomum verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Clausena excavata		LOTUS database
Curcuma amanda Roxb	Plant	KNApSAcK
Drimys winteri		LOTUS database
Elettaria cardamomum		LOTUS database
Eremanthus arboreus		LOTUS database
Eremophila longifolia	Plant	KNApSAcK
Forsythia suspensa	Plant	KNApSAcK
fragrans		Not Available
Gundelia tournefortii		LOTUS database
Ilex paraguariensis		LOTUS database
Illicium anisatum		LOTUS database
Illicium difengpi		LOTUS database
Illicium dunnianum		LOTUS database
Illicium parviflorum		LOTUS database
Illicium religiosum	Plant	KNApSAcK
Illicium verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Juniperus comitana		LOTUS database
Juniperus rigida		LOTUS database
Juniperus scopulorum	Plant	KNApSAcK
Lantana strigocamara		LOTUS database
Laureliopsis philippiana		LOTUS database
Ligusticum jeholense	Plant	KNApSAcK
Lindera neesiana	Plant	KNApSAcK
Magnolia montana		LOTUS database
Magnolia salicifolia	Plant	KNApSAcK
Mikania cordifolia		LOTUS database
Myristica fragrans	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Nectandra angustifolia		LOTUS database
Nectandra hihua		LOTUS database
Nemuaron humboldtii	Plant	KNApSAcK
Nemuaron vieillardii		LOTUS database
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Ocotea longifolia		LOTUS database
Ocotea odorifera		LOTUS database
Ocotea pretiosa	Plant	KNApSAcK
Peperomia bracteata		LOTUS database
Peperomia rotundifolia		LOTUS database
Pimpinella anisum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper aduncum	Plant	KNApSAcK
Piper auritum		LOTUS database
Piper betle		LOTUS database
Piper guineense		LOTUS database
Piper marginatum		LOTUS database
Piper nigrum		LOTUS database
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper sanctum		LOTUS database
Piper sylvestre		LOTUS database
Polygala senega		LOTUS database
Salvia rosmarinus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Sassafras albidum	Plant	KNApSAcK
Sassafras randaiense		LOTUS database
Sequoiadendron giganteum		LOTUS database
Swertia japonica		LOTUS database
Tamarindus indica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Virola surinamensis		LOTUS database
Zieria laevigata		LOTUS database
Zingiber officinale	Plant	KNApSAcK
Zinnia elegans		LOTUS database

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Benzenoid
Oxacycle
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:8994 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	11.2 °C	Not Available
Boiling Point	232–234 °C	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	1.24 g/L	ALOGPS
logP	2.23	ALOGPS
logP	2.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	18.46 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	46.11 m³·mol⁻¹	ChemAxon
Polarizability	17.24 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033591

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Safrole

METLIN ID

Not Available

PubChem Compound

5144

PDB ID

Not Available

ChEBI ID

8994

Good Scents ID

Not Available

References

General References

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 ]
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 ]
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 ]
Benedetti MS, Malnoe A, Broillet AL: Absorption, metabolism and excretion of safrole in the rat and man. Toxicology. 1977 Feb;7(1):69-83. doi: 10.1016/0300-483x(77)90039-7. [PubMed:14422 ]
Authors unspecified: Safrole. Rep Carcinog. 2002;10:213-4. [PubMed:15334724 ]
Xiao WW, Zhang HL, Wang CF, Chen Y, Zhan R, Li D, Shao LD: Chemical Synthesis Enables the Configurational Determination of Myristriol, a Highly Oxygenated Phenylpropanoid from Myristica fragrans Houtt. Chem Biodivers. 2023 Mar;20(3):e202201075. doi: 10.1002/cbdv.202201075. Epub 2023 Feb 20. [PubMed:36762483 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for Safrole (NP0000030)

MOL for NP0000030 (Safrole)

3D MOL for NP0000030 (Safrole)

3D SDF for NP0000030 (Safrole)

3D-SDF for NP0000030 (Safrole)

PDB for NP0000030 (Safrole)

3D PDB for NP0000030 (Safrole)

SMILES for NP0000030 (Safrole)

INCHI for NP0000030 (Safrole)

Structure for NP0000030 (Safrole)

3D Structure for NP0000030 (Safrole)