Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H12O |
| Molecular Weight | 148.2017 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=C(CC=C)C=C1
InChI
InChIKey=ZFMSMUAANRJZFM-UHFFFAOYSA-N
InChI=1S/C10H12O/c1-3-4-9-5-7-10(11-2)8-6-9/h3,5-8H,1,4H2,2H3
| Molecular Formula | C10H12O |
| Molecular Weight | 148.2017 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Estragole (ES) is a natural constituent of a number of plants (e.g. tarragon, sweet basil and sweet fennel) and their essential oils have been widely used in foodstuffs as flavouring agents. Estragole ES was given GRAS Generally Recognized As Safe status by the Flavor and Extract Manufacturer’s Association FEMA, 1965 and is approved by the Food and Drug Administration for food use 21 CFR code of Federal Regulation 121.1164 . Several studies with oral, i.p. or s.c. administration to CD-1 and B6C3F1 mice have shown the carcinogenicity of ES. In vivo and in vitro experimental assays have shown that EST has sedative, anticonvulsant, antioxidant, antimicrobial, and anesthetic activity.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Possible involvement of genotoxic mechanisms in estragole-induced hepatocarcinogenesis in rats. | 2012-10 |
|
| Ocimum sanctum essential oil and its active principles exert their antifungal activity by disrupting ergosterol biosynthesis and membrane integrity. | 2010-12 |
|
| Volatile constituents and biological activities of Pycnostachys abyssinica and Pycnostachys eminii extracts. | 2010-12 |
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| Chemical composition of the essential oil of Feronia elephantum Correa. | 2010-11 |
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| Sphaeranthus indicus Linn.: A phytopharmacological review. | 2010-10 |
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| Enhancement of the Norfloxacin Antibiotic Activity by Gaseous Contact with the Essential Oil of Croton zehntneri. | 2010-10 |
|
| Toxicology and carcinogenesis studies of isoeugenol (CAS No. 97-54-1) in F344/N rats and B6C3F1 mice (gavage studies). | 2010-09 |
|
| Volatile fraction of lavender and bitter fennel infusion extracts. | 2010-09 |
|
| Volatile compounds from Tagetes pusilla (Asteraceae) collected from the Venezuela Andes. | 2010-08 |
|
| Identification of nevadensin as an important herb-based constituent inhibiting estragole bioactivation and physiology-based biokinetic modeling of its possible in vivo effect. | 2010-06-01 |
|
| A physiologically based biodynamic (PBBD) model for estragole DNA binding in rat liver based on in vitro kinetic data and estragole DNA adduct formation in primary hepatocytes. | 2010-05-15 |
|
| [Effect of hepatocarcinogenicity of estragole on the glucocorticoid-mediated induction of liver-specific enzymes and the activity of the transcription factors FOXA and HNF4 in the liver of mouse and rat]. | 2010-05-01 |
|
| Predicting the hepatocarcinogenic potential of alkenylbenzene flavoring agents using toxicogenomics and machine learning. | 2010-03-15 |
|
| In vitro antimicrobial activity and chemical composition of the essential oil of Foeniculum vulgare Mill. | 2010-03-06 |
|
| Foeniculum vulgare essential oils: chemical composition, antioxidant and antimicrobial activities. | 2010-02 |
|
| In silico methods for physiologically based biokinetic models describing bioactivation and detoxification of coumarin and estragole: implications for risk assessment. | 2010-02 |
|
| Evaluation of human interindividual variation in bioactivation of estragole using physiologically based biokinetic modeling. | 2010-02 |
|
| Risk assessment of consumption of methylchavicol and tarragon: the genotoxic potential in vivo and in vitro. | 2010-02 |
|
| Ocimum sanctum Linn. A reservoir plant for therapeutic applications: An overview. | 2010-01 |
|
| QCM-arrays for sensing terpenes in fresh and dried herbs via bio-mimetic MIP layers. | 2010 |
|
| Study of the metabolism of estragole in humans consuming fennel tea. | 2009-12 |
|
| Determination of alkenylbenzenes and related flavour compounds in food samples by on-column preconcentration-capillary liquid chromatography. | 2009-10-23 |
|
| [Advance in chemical constituents of genus Clematis]. | 2009-10 |
|
| Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared with male rats. | 2009-08 |
|
| Characterization of volatile substances in apples from Rosaceae family by headspace solid-phase microextraction followed by GC-qMS. | 2009-06 |
|
| Correlation between hepatocarcinogenic effect of estragole and its influence on glucocorticoid induction of liver-specific enzymes and activities of FOXA and HNF4 transcription factors in mouse and rat liver. | 2009-04 |
|
| Insecticidal activity of basil oil, trans-anethole, estragole, and linalool to adult fruit flies of Ceratitis capitata, Bactrocera dorsalis, and Bactrocera cucurbitae. | 2009-02 |
|
| Identification of the chemotypes of Ocimum forskolei and Ocimum basilicum by NMR spectroscopy. | 2008-11 |
|
| Activity of essential oils and individual components against acetyl- and butyrylcholinesterase. | 2008-09-25 |
|
| A physiologically based biokinetic (PBBK) model for estragole bioactivation and detoxification in rat. | 2008-09-01 |
|
| Chemical constituents and larvicidal property of the essential oil of Blumea mollis (D. Don) Merr. against Culex quinquefasciatus. | 2008-09 |
|
| Mountain pine beetle attack associated with low levels of 4-allylanisole in ponderosa pine. | 2008-08 |
|
| Chemical composition and antimicrobial activities of the essential oil from the seeds of Enterolobium contortisiliquum (leguminosae). | 2008-08 |
|
| Antifungal activity of essential oils of Croton species from the Brazilian Caatinga biome. | 2008-05 |
|
| Yield and oil composition of 38 basil (Ocimum basilicum L.) accessions grown in Mississippi. | 2008-01-09 |
|
| In silico toxicological screening of natural products. | 2008 |
|
| Characteristics of fatty acids and essential oil from sweet fennel (Foeniculum vulgare Mill. var. dulce) and bitter fennel fruits (F. vulgare Mill. var. vulgare) growing in Turkey. | 2008 |
|
| Effects of anethole and structural analogues on the contractility of rat isolated aorta: Involvement of voltage-dependent Ca2+-channels. | 2007-09-08 |
|
| A pinoresinol-lariciresinol reductase homologue from the creosote bush (Larrea tridentata) catalyzes the efficient in vitro conversion of p-coumaryl/coniferyl alcohol esters into the allylphenols chavicol/eugenol, but not the propenylphenols p-anol/isoeugenol. | 2007-09-01 |
|
| Herbal medicines: can we do without pharmacologist? | 2007-09 |
|
| [Influence of age and sex on hepatotoxic and hypothermic effects of estrogole in mice]. | 2007-08 |
|
| Metabolic activation of herbal and dietary constituents and its clinical and toxicological implications: an update. | 2007-08 |
|
| Tandem mass spectrometry analysis of N2-(trans-Isoestragol-3'-yl)-2'-deoxyguanosine as a strategy to study species differences in sulfotransferase conversion of the proximate carcinogen 1'-hydroxyestragole. | 2007-07 |
|
| Human cytochrome p450 enzyme specificity for the bioactivation of estragole and related alkenylbenzenes. | 2007-05 |
|
| Characterization of aniseed-flavoured spirit drinks by headspace solid-phase microextraction gas chromatography-mass spectrometry and chemometrics. | 2007-04-30 |
|
| Use of biomonitoring data to evaluate methyl eugenol exposure. | 2006-11 |
|
| Character impact odorants of fennel fruits and fennel tea. | 2006-05-17 |
|
| Comparative essential oil composition and antifungal effect of bitter fennel (Foeniculum vulgare ssp. piperitum) fruit oils obtained during different vegetation. | 2006 |
|
| A source of almost pure methyl chavicol: volatile oil from the aerial parts of Tagetes lucida (Asteraceae) cultivated in Costa Rica. | 2004-12 |
|
| Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole. | 1983-03 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: BALB-c mice, in groups of five animals
to each dose, were orally treated with Estragole (250, 500, or
750 mg/kg) 30 min before the intraperitoneal injection carrageenan solution (500 ug/mice).
In the peritonitis model, Estragole (500 and 750 mg/kg) decreased the infiltration of peritoneal exudate leukocytes.
Route of Administration:
Oral
In vitro chemotaxis assay showed that Estragole (3, 10, 30, and 60 ug/mL) inhibited murine neutrophil migration toward fMLP. Estragole (3, 10, and 30 ug/mL) was able to stimulate the macrophages phagocytosis but only at concentration of 10 ug/mL promoted an increase in nitric oxide (NO) production.
| Substance Class |
Chemical
Created
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admin
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| Record UNII |
9NIW07V3ET
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| Record Status |
Validated (UNII)
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CFR |
21 CFR 172.515
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EPA PESTICIDE CODE |
62150
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JECFA EVALUATION |
ESTRAGOLE
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205-427-8
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9NIW07V3ET
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C007633
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8815
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ESTRAGOLE
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5412
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100000177051
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1767
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m5030
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PRIMARY | Merck Index | ||
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DTXSID0020575
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140-67-0
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404113
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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 |
