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

Synonym	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
4-Allyl-1,2-(methylenedioxy)benzene, 8CI	db_source
5-(2-Propenyl)-1,3-benzodioxole, 9CI	db_source
5-Allyl-1,3-benzodioxolerlet DS Base	biospider

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

Property	Value	Reference
Physical state	Liquid
Physical Description	Not Available
Mass Composition	C 74.06%; H 6.21%; O 19.73%	DFC
Melting Point	Fp 11.2°	DFC
Boiling Point	Bp6 104-105°	DFC
Experimental Water Solubility	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	n20D 1.5383	DFC

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

Food	Content Range	Average	Reference
Food			Reference

Biological Effects and Interactions

Health Effects / Bioactivities

Descriptor	ID	Definition	Reference
Anesthetic		A drug that induces a reversible loss of sensation, used to prevent pain and discomfort during medical procedures, surgeries, and diagnostic tests, promoting patient comfort and facilitating treatment.	DUKE
Anti-aggregant		An agent that prevents platelet aggregation, reducing blood clot formation. Its biological role is to inhibit platelet activation, and its therapeutic applications include preventing thrombosis and stroke. Key medical uses include treating cardiovascular diseases, such as myocardial infarction and atrial fibrillation, and managing conditions that increase the risk of blood clots.	DUKE
Anti bacterial	33282	An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.	DUKE
Anti convulsant	52217	An agent that reduces or prevents seizures, commonly used in managing epilepsy, neuropathic pain, and mood disorders, by stabilizing abnormal electrical activity in the brain.	DUKE
Anti septic	33281	An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.	DUKE
Calcium antagonist	48706	A medication that blocks calcium ion entry into cells, reducing muscle contraction and vascular resistance. It treats hypertension, angina, and arrhythmias by dilating blood vessels and decreasing cardiac workload, commonly used in managing cardiovascular diseases.	DUKE
Cancer preventive	35610	An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.	DUKE
Carcinogenic	50903	An agent that causes cancer, damaging cellular DNA and disrupting normal cell growth. It has no therapeutic applications, but understanding its biological role informs cancer prevention and treatment strategies, with key medical uses in oncology research and risk assessment.	DUKE
Carminative		An agent that prevents or relieves gas in the gastrointestinal tract, facilitating its expulsion and combating flatulence, commonly used to soothe digestive issues and alleviate symptoms of bloating and discomfort.	DUKE
Central nervous system depressant	35470	An agent that slows brain activity, reducing anxiety, stress, and excitability. Therapeutically, it's used to manage insomnia, seizures, and anxiety disorders, promoting relaxation and sedation. Key medical uses include treating insomnia, epilepsy, and panic disorders, as well as inducing anesthesia.	DUKE
Central nervous system stimulant	35470	An agent that increases alertness and activity by enhancing neurotransmitter release, used therapeutically to manage attention deficit hyperactivity disorder (ADHD), narcolepsy, and fatigue, and to improve cognitive function and mood.	DUKE
Controlled		A substance or behaviour regulated by external factors, such as laws or medical supervision. Its biological role involves moderation of potentially harmful activities. Therapeutically, controlled substances have applications in pain management and addiction treatment. Key medical uses include managing chronic pain, anxiety, and insomnia, while minimizing abuse and dependence risks.	DUKE
Cytochrome-p450 inducer		An agent that stimulates cytochrome-p450 enzyme activity, enhancing drug metabolism. Therapeutically, it increases clearance of toxic substances and certain medications, with applications in managing drug interactions, toxic exposures, and some cancers.	DUKE
Cytochrome-p488 inducer		An agent that stimulates the activity of cytochrome-p488 enzymes, enhancing drug metabolism and detoxification. Therapeutically, it aids in managing drug interactions and toxicity, with potential applications in cancer treatment and pharmacokinetic enhancement.	DUKE
DNA-binder		An agent that binds to DNA, regulating gene expression and replication. It has therapeutic applications in gene therapy, cancer treatment, and antimicrobial therapy, with key medical uses including targeting viral DNA and modulating immune responses.	DUKE
Hepatocarcinogenic	50903	An agent that promotes the development of liver cancer, having a harmful biological role. It has no therapeutic applications, but understanding its effects is crucial in liver cancer research and prevention. Key medical uses include studying liver carcinogenesis and developing strategies to mitigate its harmful effects.	DUKE
Hepatoregenerative	62868	An agent that promotes liver regeneration and repair, supporting the biological role of liver tissue restoration. It has therapeutic applications in treating liver diseases, such as cirrhosis and hepatitis, and key medical uses include enhancing liver function and reducing liver damage.	DUKE
Hepatotoxic	50908	An agent that causes liver damage or toxicity, disrupting normal liver function. It has no therapeutic applications, but is often a side effect of certain medications, such as acetaminophen overdose, and is a key consideration in medical uses, including monitoring liver function during drug therapy.	DUKE
Hypothermic		A condition of abnormally low body temperature, playing a biological role in reducing metabolic rate and oxygen demand. Therapeutically, it has applications in neuroprotection, cardiac surgery, and trauma care. Key medical uses include treating heatstroke, cardiac arrest, and brain injuries, as well as preserving organs for transplantation.	DUKE
Irritant		An agent that causes slight inflammation or discomfort, stimulating a biological response. Therapeutically, it can be used to increase blood flow or stimulate healing. Key medical uses include treating wounds, skin conditions, and respiratory issues, such as congestion, by inducing a mild inflammatory response to promote recovery.	DUKE
Mutagenic		An agent that induces genetic mutations, altering DNA sequences. It plays a biological role in evolution and adaptation. Therapeutically, mutagenic agents are used in cancer treatment, such as chemotherapy, and in gene therapy to introduce beneficial traits. Key medical uses include oncology and genetic research.	DUKE
Nematicide	25491	An agent that kills nematodes, a type of parasitic worm, used to control infestations in crops and animals, with therapeutic applications in veterinary medicine to treat parasitic infections and promote livestock health.	DUKE
Neurotoxic	50910	A substance that damages or destroys nerve cells, disrupting normal brain function. It has no therapeutic applications, but is used in research to study neurodegenerative diseases. Key medical uses include understanding and developing treatments for conditions like Alzheimer's and Parkinson's diseases, where neurotoxicity plays a role.	DUKE
Pediculicide	38706	An agent that kills lice, used to treat infestations such as head lice, body lice, and pubic lice, reducing discomfort and preventing the spread of diseases like typhus and trench fever.	DUKE
Perfumery	48318	The art of creating fragrances, playing a biological role in emotional and sensory stimulation. Therapeutically, perfumery has applications in aromatherapy, reducing stress and anxiety. Key medical uses include mood enhancement, pain management, and promoting relaxation, with certain scents exhibiting anti-anxiety and anti-depressant properties.	DUKE
Pesticide	25944	An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.	DUKE
Psychoactive	35471	A substance that affects brain function, altering mood, perception, or consciousness. It plays a biological role in modifying neurotransmitter activity. Therapeutically, psychoactive substances have applications in managing mental health disorders, such as depression and anxiety. Key medical uses include treating psychiatric conditions, including attention deficit hyperactivity disorder (ADHD), and certain sleep disorders.	DUKE
Tremorigenic		An agent that induces tremors, causing involuntary muscle contractions and relaxation, often used in research to study movement disorders, with potential therapeutic applications in neurology and psychiatry, particularly in managing conditions like Parkinson's disease and essential tremor.	DUKE

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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