Showing Compound Safrole (FDB011672)

Record Information

Version

1.0

Creation date

2010-04-08 22:09:46 UTC

Update date

2019-11-26 03:05:14 UTC

Primary ID

FDB011672

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Safrole

Description

Occurs 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 Number

94-59-7

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(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
1,2-Methylenedioxy-4-allylbenzene	ChEBI
1-Allyl,3,4-methylenedioxy benzene	HMDB
1-Allyl-3,4-methylenedioxybenzene	ChEBI
3, 4-(Methylenedioxy)allylbenzene	HMDB

Showing 1 to 10 of 48 entries

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

Chemical Formula

C10H10O2

IUPAC name

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

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

Isomeric SMILES

C=CCC1=CC2=C(OCO2)C=C1

Average Molecular Weight

162.1852

Monoisotopic Molecular Weight

162.068079564

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.

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 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Environmental:

Tobacco smoke

Biological:

Plant

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition

Household products:

Pesticide:

Insecticide

Environmental role:

Air pollutant

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp6 104-105°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 74.06%; H 6.21%; O 19.73%	DFC
Melting Point	Fp 11.2°	DFC
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-0ik9-4900000000-9558c12b4c5a01a27490	2014-09-20	View Spectrum
GC-MS	Safrole, non-derivatized, GC-MS Spectrum	splash10-0ik9-3900000000-27e98ee529004a2d8b66	Spectrum
GC-MS	Safrole, non-derivatized, GC-MS Spectrum	splash10-0ik9-6900000000-54b4c1509456711936df	Spectrum
GC-MS	Safrole, non-derivatized, GC-MS Spectrum	splash10-03di-6900000000-87b7efd770862a8f97a5	Spectrum
GC-MS	Safrole, non-derivatized, GC-MS Spectrum	splash10-0ik9-5900000000-0e7164aea8e5fa73ab55	Spectrum
GC-MS	Safrole, non-derivatized, GC-MS Spectrum	splash10-03di-0900000000-cae3268c72651c72100c	Spectrum
GC-MS	Safrole, non-derivatized, GC-MS Spectrum	splash10-0ik9-3900000000-27e98ee529004a2d8b66	Spectrum
GC-MS	Safrole, non-derivatized, GC-MS Spectrum	splash10-0ik9-6900000000-54b4c1509456711936df	Spectrum
GC-MS	Safrole, non-derivatized, GC-MS Spectrum	splash10-03di-6900000000-87b7efd770862a8f97a5	Spectrum
GC-MS	Safrole, non-derivatized, GC-MS Spectrum	splash10-0ik9-5900000000-0e7164aea8e5fa73ab55	Spectrum
GC-MS	Safrole, non-derivatized, GC-MS Spectrum	splash10-03di-0900000000-cae3268c72651c72100c	Spectrum
Predicted GC-MS	Safrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-01sa-2900000000-390702c1e607859e4700	Spectrum
Predicted GC-MS	Safrole, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-ce90b24b2ef83a609261	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-1900000000-cb602c608751e483efce	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udl-9600000000-85407378b64267759f6d	2016-08-02	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-f5650e9b49b023a3cfd2	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-9dbd3903283425175546	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02ti-5900000000-4204c0caaf5bb9b5d258	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03di-0900000000-9b0c6d7bc981d77b1927	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03k9-0900000000-01530378eccaf5c845f0	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fvr-9400000000-d251b0867c3f55c2e90e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-4d3d221c51bdf4e740a2	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-0900000000-3a92a79dc10e1183839f	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01ot-7900000000-1024f7dba32bfc58ce37	2021-09-25	View Spectrum

NMR

Type	Description		View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)		Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)		Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB33591

CRC / DFC (Dictionary of Food Compounds) ID

GXV45-I:GXV45-I

EAFUS ID

3354

Dr. Duke ID

SAFROLE

BIGG ID

Not Available

KNApSAcK ID

C00002771

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

94-59-7

GoodScent ID

rw1010791

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
anesthetic			DUKE
anti aggregant			DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti convulsant	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti septic	33281	A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.	DUKE
calcium antagonist	48706	Substance that attaches to and blocks cell receptors that normally bind naturally occurring substances.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
carcinogenic	50903	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
carminative			DUKE
central nervous system depressant	35470	A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.	DUKE

Showing 1 to 10 of 28 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
anise	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sassafrass	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spice	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
spicy	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sweet	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
warm	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 The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.