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Details

Stereochemistry ACHIRAL
Molecular Formula C10H10O2
Molecular Weight 162.1856
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SAFROLE

SMILES

C=CCc1ccc2c(c1)OCO2

InChI

InChIKey=ZMQAAUBTXCXRIC-UHFFFAOYSA-N
InChI=1S/C10H10O2/c1-2-3-8-4-5-9-10(6-8)12-7-11-9/h2,4-6H,1,3,7H2

HIDE SMILES / InChI

Molecular Formula C10H10O2
Molecular Weight 162.1856
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Safrole is a natural product obtained from essential oil of the root bark of Sassafras tree. Safrole has been used as a flavoring agent in drugs and in the manufacture of heliotropin, perfumes, soaps, and piperonyl butoxide. Oil of sassafras, which contains safrole, was formerly used to flavor some soft drinks, such as root beer. However, this use or any other addition of safrole or oil of sassafras to food was banned in the United States in 1960 due to evidence of carcinogenicity. Numerous studies have shown that safrole from betel quid-containing safrole might be involved in the pathogenesis of hepatocellular carcinoma in human due to the formation of DNA adducts. Safrole has also been used in the illicit production of the drug 3,4-methylenedioxymethamphetamine (MDMA, or ecstasy), and the U.S. Drug Enforcement Administration has designated safrole a List I Chemical. Anticancer and anti-diabetic properties of safrole were investigated in vitro and in vivo.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2311221
Target ID: P05177
Gene ID: 1544.0
Gene Symbol: CYP1A2
Target Organism: Homo sapiens (Human)
5.7 µM [IC50]
Target ID: P11509|||Q4VAU1
Gene ID: 1548.0
Gene Symbol: CYP2A6
Target Organism: Homo sapiens (Human)
12.0 µM [IC50]
Target ID: P05181
Gene ID: 1571.0
Gene Symbol: CYP2E1
Target Organism: Homo sapiens (Human)
1.7 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Safrole.
2002
[Analysis of volatile constituents of root and rhizome of Asarum heterotropoides Fr. var. mandshuricum (Maxim.) Kitag. by gas chromatography-mass spectrometry].
2002 Sep
Age-related differences in susceptibility to carcinogenesis: a quantitative analysis of empirical animal bioassay data.
2004 Aug
Antimycobacterial compounds from Piper sanctum.
2004 Dec
Synthesis, antitumour and antimicrobial activities of new peptidyl derivatives containing the 1,3-benzodioxole system.
2004 Dec
Effects of arecoline, safrole, and nicotine on collagen phagocytosis by human buccal mucosal fibroblasts as a possible mechanism for oral submucous fibrosis in Taiwan.
2004 Oct
Safrole oxide induces apoptosis in A549 human lung cancer cells.
2004 Sep
The chemical composition of some Lauraceae essential oils and their antifungal activities.
2004 Sep
Human cytochrome p450 enzyme specificity for bioactivation of safrole to the proximate carcinogen 1'-hydroxysafrole.
2004 Sep
Genotoxic effects of eugenol, isoeugenol and safrole in the wing spot test of Drosophila melanogaster.
2005 Apr 4
Conformationally induced electrostatic stabilization of persulfoxides: a new suggestion for inhibition of physical quenching of singlet oxygen by remote functional groups.
2005 Aug 24
Expeditious synthesis of bioactive allylphenol constituents of the genus Piper through a metal-free photoallylation procedure.
2005 Aug 7
Basic and neutral route specific impurities in MDMA prepared by different synthesis methods. Comparison of impurity profiles.
2005 Dec 20
Safrole-DNA adducts in tissues from esophageal cancer patients: clues to areca-related esophageal carcinogenesis.
2005 Jan 3
Independent [Ca2+]i increases and cell proliferation induced by the carcinogen safrole in human oral cancer cells.
2005 Jul
Flavonoids and alkenylbenzenes: mechanisms of mutagenic action and carcinogenic risk.
2005 Jul 1
An experimental study of sexual function improving effect of Myristica fragrans Houtt. (nutmeg).
2005 Jul 20
Probing the mechanism of sulfoxide-catalyzed hemiacetal activation in dehydrative glycosylation.
2005 Jul 22
Increased sulfur precursors and volatiles production by the leek Allium porrum in response to specialist insect attack.
2005 Jun
Inhibition of human cytochrome P450 enzymes by the natural hepatotoxin safrole.
2005 May
'Non-covalent synthesis' of a chiral host of calix[6]arene and enantiomeric discrimination.
2005 May
Nutmeg intoxication in Texas, 1998-2004.
2005 Nov
A traditional method of Cinnamomum carolinense preparation eliminates safrole from a therapeutic Pohnpean tea.
2005 Nov 14
Upregulating of Fas, integrin beta4 and P53 and depressing of PC-PLC activity and ROS level in VEC apoptosis by safrole oxide.
2005 Oct 24
Assessing susceptibility from early-life exposure to carcinogens.
2005 Sep
Neopetrosiamides, peptides from the marine sponge Neopetrosia sp. that inhibit amoeboid invasion by human tumor cells.
2005 Sep 15
Safrole-induced Ca2+ mobilization and cytotoxicity in human PC3 prostate cancer cells.
2006
Co-lyophilization with D-proline greatly enhances peroxidase's stereoselectivity in a non-aqueous medium.
2006 Apr
The sulphoxidation of S-carboxymethyl-L-cysteine in COPD.
2006 Apr
Safrole oxide induces apoptosis by up-regulating Fas and FasL instead of integrin beta4 in A549 human lung cancer cells.
2006 Apr 1
Abuse of nutmeg (Myristica fragrans Houtt.): studies on the metabolism and the toxicologic detection of its ingredients elemicin, myristicin, and safrole in rat and human urine using gas chromatography/mass spectrometry.
2006 Aug
Safrole-induced cellular Ca2+ increases and death in human osteosarcoma cells.
2006 Aug
Aryl sulfoxide radical cations. Generation, spectral properties, and theoretical calculations.
2006 Aug 17
Design and synthesis of 3,4-methylenedioxy-6-nitrophenoxyacetylhydrazone derivatives obtained from natural safrole: new lead-agents with analgesic and antipyretic properties.
2006 Dec 1
Thioether sulfur oxygenation from O2 or H2O2 reactivity of copper complexes with tridentate N2Sthioether ligands.
2006 Dec 11
Synthesis by-products from the Wacker oxidation of safrole in methanol using rho-benzoquinone and palladium chloride.
2006 Dec 20
Safrole oxide induced human umbilical vein vascular endothelial cell differentiation into neuron-like cells by depressing the reactive oxygen species level at the low concentration.
2006 Feb
Do ion tethered functional groups affect IL solvent properties? The case of sulfoxides and sulfones.
2006 Feb 14
Conformational arm-wrestling: battles for stereochemical control in benzamides bearing matched and mismatched chiral 2- and 6-substituents.
2006 Feb 7
Safrole oxide induces apoptosis by activating caspase-3, -8, and -9 in A549 human lung cancer cells.
2006 Jan 1
[Analysis of disulfoton sulfoxide in chingentsuai by pulsed splitless mass spectrometry using programmed temperature vaporization (PTV) inlet].
2006 Jun
Racemic and chiral sulfoxides as potential prodrugs of the COX-2 inhibitors Vioxx and Arcoxia.
2006 Jun 15
[Comparing analysis of components in volatile oils of nutmeg and prepared nutmeg by GC-MS].
2006 May
Genotoxicity and endoreduplication inducing activity of the food flavouring eugenol.
2006 May
Phototoxicity testing by online irradiation and HPLC.
2006 Nov
Illuminating cancer health disparities using ethnogenetic layering (EL) and phenotype segregation network analysis (PSNA).
2006 Spring
Safrole oxide induces neuronal apoptosis through inhibition of integrin beta4/SOD activity and elevation of ROS/NADPH oxidase activity.
2007 Feb 20
Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells.
2007 Jan 18
Elevated expression of NF-kappaB in oral submucous fibrosis--evidence for NF-kappaB induction by safrole in human buccal mucosal fibroblasts.
2007 Jul
Synthesis and antitumour evaluation of peptidyl-like derivatives containing the 1,3-benzodioxole system.
2007 Mar
Patents

Sample Use Guides

As a food additive, safrole was consumed orally. The addition of safrole to food, however, was banned in 1960.
Route of Administration: Oral
The ability of safrole to inhibit cytochromes was investigated using recombinant human P450s expressed in E.Coli. Oxidations were initiated by the addition of a NADPH-generating system containing NADP, glucose-6-phosphate, and glucose-6-phosphate dehydrogenase. Duplicated reactions were carried out at 37 C with shaking for 10–20 min. Stock solution of safrole was prepared using methanol and the final content of methanol was less than 1% in the reaction volume of 0.2–1.0 ml. The same amount of methanol was added in the control reactions.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:42:40 UTC 2021
Edited
by admin
on Fri Jun 25 22:42:40 UTC 2021
Record UNII
RSB34337V9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SAFROLE
MI  
Systematic Name English
5-(2-PROPENYL)-1,3-BENZODIOXOLE
Systematic Name English
5-PROP-2-ENYL-1,3-BENZODIOXOLE
Systematic Name English
SAFROLE [IARC]
Common Name English
4-ALLYL-1,2-METHYLENEDIOXYBENZENE
Systematic Name English
M-ALLYL PYROCATECHINMETHYLENE ETHER
Common Name English
NSC-11831
Code English
SHIKOMOL
Common Name English
SAFROLE [MI]
Common Name English
SAFROLE [USP-RS]
Common Name English
RHYUNO OIL
Common Name English
BENZENE, 4-ALLYL-1,2-(METHYLENEDIOXY)-
Systematic Name English
1-ALLYL-3,4-METHYLENEDIOXYBENZENE
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 189.180
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
JECFA EVALUATION SAFROLE AND ISOSAFROLE
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
NCI_THESAURUS C45187
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
202-345-4
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
RXCUI
2383532
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
ChEMBL
CHEMBL242273
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
WIKIPEDIA
SAFROLE
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
MERCK INDEX
M9723
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1607299
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY USP-RS
EVMPD
SUB64305
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
MESH
D012451
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
FDA UNII
RSB34337V9
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
EPA CompTox
94-59-7
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
CAS
94-59-7
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
NCI_THESAURUS
C44443
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
PUBCHEM
5144
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
HSDB
2653
Created by admin on Fri Jun 25 22:42:40 UTC 2021 , Edited by admin on Fri Jun 25 22:42:40 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT MAY BE PRESENT
ASSAY (GC)
PARENT -> CONSTITUENT ALWAYS PRESENT
A cinnamon leaf oil of Chinese origin, Cinnamomun japonicum Sieb., contains a high concentration of safrole (60%) and only about 3% eugenol.
PARENT -> CONSTITUENT MAY BE PRESENT
ASSAY (GC)