Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H10O2 |
| Molecular Weight | 162.1852 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C=CCC1=CC=C2OCOC2=C1
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
| Molecular Formula | C10H10O2 |
| Molecular Weight | 162.1852 |
| 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
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2311221 |
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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
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Elevated expression of NF-kappaB in oral submucous fibrosis--evidence for NF-kappaB induction by safrole in human buccal mucosal fibroblasts. | 2007-07 |
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| Synthesis and antitumour evaluation of peptidyl-like derivatives containing the 1,3-benzodioxole system. | 2007-03 |
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| Safrole oxide induces neuronal apoptosis through inhibition of integrin beta4/SOD activity and elevation of ROS/NADPH oxidase activity. | 2007-02-20 |
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| Antiproliferative and pro-apoptotic activity of eugenol-related biphenyls on malignant melanoma cells. | 2007-01-18 |
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| Synthesis by-products from the Wacker oxidation of safrole in methanol using rho-benzoquinone and palladium chloride. | 2006-12-20 |
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| Thioether sulfur oxygenation from O2 or H2O2 reactivity of copper complexes with tridentate N2Sthioether ligands. | 2006-12-11 |
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| Design and synthesis of 3,4-methylenedioxy-6-nitrophenoxyacetylhydrazone derivatives obtained from natural safrole: new lead-agents with analgesic and antipyretic properties. | 2006-12-01 |
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| Use of biomonitoring data to evaluate methyl eugenol exposure. | 2006-11 |
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| Phototoxicity testing by online irradiation and HPLC. | 2006-11 |
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| Aryl sulfoxide radical cations. Generation, spectral properties, and theoretical calculations. | 2006-08-17 |
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| 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. | 2006-08 |
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| Safrole-induced cellular Ca2+ increases and death in human osteosarcoma cells. | 2006-08 |
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| Racemic and chiral sulfoxides as potential prodrugs of the COX-2 inhibitors Vioxx and Arcoxia. | 2006-06-15 |
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| Identification of an indole series of prostaglandin D2 receptor antagonists. | 2006-06-01 |
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| [Analysis of disulfoton sulfoxide in chingentsuai by pulsed splitless mass spectrometry using programmed temperature vaporization (PTV) inlet]. | 2006-06 |
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| [Comparing analysis of components in volatile oils of nutmeg and prepared nutmeg by GC-MS]. | 2006-05 |
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| Genotoxicity and endoreduplication inducing activity of the food flavouring eugenol. | 2006-05 |
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| Safrole oxide induces apoptosis by up-regulating Fas and FasL instead of integrin beta4 in A549 human lung cancer cells. | 2006-04-01 |
|
| Co-lyophilization with D-proline greatly enhances peroxidase's stereoselectivity in a non-aqueous medium. | 2006-04 |
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| The sulphoxidation of S-carboxymethyl-L-cysteine in COPD. | 2006-04 |
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| Do ion tethered functional groups affect IL solvent properties? The case of sulfoxides and sulfones. | 2006-02-14 |
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| Conformational arm-wrestling: battles for stereochemical control in benzamides bearing matched and mismatched chiral 2- and 6-substituents. | 2006-02-07 |
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| 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. | 2006-02 |
|
| Theory and use of the pseudophase model in gas-liquid chromatographic enantiomeric separations. | 2006-01-01 |
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| Safrole oxide induces apoptosis by activating caspase-3, -8, and -9 in A549 human lung cancer cells. | 2006-01-01 |
|
| Illuminating cancer health disparities using ethnogenetic layering (EL) and phenotype segregation network analysis (PSNA). | 2006 |
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| Safrole-induced Ca2+ mobilization and cytotoxicity in human PC3 prostate cancer cells. | 2006 |
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| Suppressing Akt phosphorylation and activating Fas by safrole oxide inhibited angiogenesis and induced vascular endothelial cell apoptosis in the presence of fibroblast growth factor-2 and serum. | 2006 |
|
| A study of impurities in intermediates and 3,4-methylenedioxymethamphetamine (MDMA) samples produced via reductive amination routes. | 2005-12-20 |
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| Basic and neutral route specific impurities in MDMA prepared by different synthesis methods. Comparison of impurity profiles. | 2005-12-20 |
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| A traditional method of Cinnamomum carolinense preparation eliminates safrole from a therapeutic Pohnpean tea. | 2005-11-14 |
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| Nutmeg intoxication in Texas, 1998-2004. | 2005-11 |
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| Upregulating of Fas, integrin beta4 and P53 and depressing of PC-PLC activity and ROS level in VEC apoptosis by safrole oxide. | 2005-10-24 |
|
| Neopetrosiamides, peptides from the marine sponge Neopetrosia sp. that inhibit amoeboid invasion by human tumor cells. | 2005-09-15 |
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| Determination of synthesis method of ecstasy based on the basic impurities. | 2005-09-10 |
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| Assessing susceptibility from early-life exposure to carcinogens. | 2005-09 |
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| Synthesis and spectroscopic behavior of highly luminescent Eu(3+)-dibenzoylmethanate (DBM) complexes with sulfoxide ligands. | 2005-09 |
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| Conformationally induced electrostatic stabilization of persulfoxides: a new suggestion for inhibition of physical quenching of singlet oxygen by remote functional groups. | 2005-08-24 |
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| Expeditious synthesis of bioactive allylphenol constituents of the genus Piper through a metal-free photoallylation procedure. | 2005-08-07 |
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| Probing the mechanism of sulfoxide-catalyzed hemiacetal activation in dehydrative glycosylation. | 2005-07-22 |
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| An experimental study of sexual function improving effect of Myristica fragrans Houtt. (nutmeg). | 2005-07-20 |
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| Flavonoids and alkenylbenzenes: mechanisms of mutagenic action and carcinogenic risk. | 2005-07-01 |
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| Discovery of a novel small molecule, 1-ethoxy-3-(3,4-methylenedioxyphenyl)-2-propanol, that induces apoptosis in A549 human lung cancer cells. | 2005-07-01 |
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| Independent [Ca2+]i increases and cell proliferation induced by the carcinogen safrole in human oral cancer cells. | 2005-07 |
|
| Increased sulfur precursors and volatiles production by the leek Allium porrum in response to specialist insect attack. | 2005-06 |
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| Safrole oxide inhibits angiogenesis by inducing apoptosis. | 2005-06 |
|
| Inhibition of human cytochrome P450 enzymes by the natural hepatotoxin safrole. | 2005-05 |
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| Genotoxic effects of eugenol, isoeugenol and safrole in the wing spot test of Drosophila melanogaster. | 2005-04-04 |
|
| [Study on chemical constituents of the essential oil from Myristica fragrans Houtt. by supercritical fluid extraction and steam distillation]. | 2004-11 |
|
| [Analysis of volatile constituents of root and rhizome of Asarum heterotropoides Fr. var. mandshuricum (Maxim.) Kitag. by gas chromatography-mass spectrometry]. | 2002-09 |
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
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admin
on
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Mon Mar 31 21:12:05 GMT 2025
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on
Mon Mar 31 21:12:05 GMT 2025
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| Record UNII |
RSB34337V9
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| Record Status |
Validated (UNII)
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| Record Version |
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CFR |
21 CFR 189.180
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DEA NO. |
8323
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JECFA EVALUATION |
SAFROLE AND ISOSAFROLE
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NCI_THESAURUS |
C45187
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100000134786
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8994
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CHEMBL242273
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SAFROLE
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m9723
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C44443
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11831
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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PARENT -> CONSTITUENT MAY BE PRESENT | |||
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PARENT -> CONSTITUENT MAY BE PRESENT | |||
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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.
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