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 |
|---|---|---|
| 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 Mar |
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| A source of almost pure methyl chavicol: volatile oil from the aerial parts of Tagetes lucida (Asteraceae) cultivated in Costa Rica. | 2004 Dec |
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| Food protective effect of acaricidal components isolated from anise seeds against the stored food mite, Tyrophagus putrescentiae (Schrank). | 2005 Jun |
|
| Chavicol formation in sweet basil (Ocimum basilicum): cleavage of an esterified C9 hydroxyl group with NAD(P)H-dependent reduction. | 2006 Jul 21 |
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| Role of capsaicin-sensitive sensory nerves in mediation of the cardiovascular effects of the essential oil of croton zehntneri leaves in anaesthetized rats. | 2006 Mar |
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| Character impact odorants of fennel fruits and fennel tea. | 2006 May 17 |
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| Use of biomonitoring data to evaluate methyl eugenol exposure. | 2006 Nov |
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| Electrophysiological responses of the lepidopterous stemborers Chilo partellus and Busseola fusca to volatiles from wild and cultivated host plants. | 2006 Nov |
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| Estragole (4-allylanisole) is the primary compound in volatiles emitted from the male and female cones of Cycas revoluta. | 2006 Nov |
|
| Quantification of flavor-related compounds in the unburned contents of bidi and clove cigarettes. | 2006 Nov 1 |
|
| Composition of the volatile fraction of Ocotea bofo Kunth (Lauraceae) calyces by GC-MS and NMR fingerprinting and its antimicrobial and antioxidant activity. | 2006 Oct 4 |
|
| Comparative essential oil composition and antifungal effect of bitter fennel (Foeniculum vulgare ssp. piperitum) fruit oils obtained during different vegetation. | 2006 Winter |
|
| Characterization of aniseed-flavoured spirit drinks by headspace solid-phase microextraction gas chromatography-mass spectrometry and chemometrics. | 2007 Apr 30 |
|
| [Influence of age and sex on hepatotoxic and hypothermic effects of estrogole in mice]. | 2007 Aug |
|
| Metabolic activation of herbal and dietary constituents and its clinical and toxicological implications: an update. | 2007 Aug |
|
| 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 Jul |
|
| Human cytochrome p450 enzyme specificity for the bioactivation of estragole and related alkenylbenzenes. | 2007 May |
|
| Herbal medicines: can we do without pharmacologist? | 2007 Sep |
|
| 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 Sep 1 |
|
| Effects of anethole and structural analogues on the contractility of rat isolated aorta: Involvement of voltage-dependent Ca2+-channels. | 2007 Sep 8 |
|
| 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 |
|
| Mountain pine beetle attack associated with low levels of 4-allylanisole in ponderosa pine. | 2008 Aug |
|
| Chemical composition and antimicrobial activities of the essential oil from the seeds of Enterolobium contortisiliquum (leguminosae). | 2008 Aug |
|
| Yield and oil composition of 38 basil (Ocimum basilicum L.) accessions grown in Mississippi. | 2008 Jan 9 |
|
| Activity of essential oils and individual components against acetyl- and butyrylcholinesterase. | 2008 Jul-Aug |
|
| Antifungal activity of essential oils of Croton species from the Brazilian Caatinga biome. | 2008 May |
|
| Identification of the chemotypes of Ocimum forskolei and Ocimum basilicum by NMR spectroscopy. | 2008 Nov |
|
| Chemical constituents and larvicidal property of the essential oil of Blumea mollis (D. Don) Merr. against Culex quinquefasciatus. | 2008 Sep |
|
| A physiologically based biokinetic (PBBK) model for estragole bioactivation and detoxification in rat. | 2008 Sep 1 |
|
| 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 Apr |
|
| Use of physiologically based biokinetic (PBBK) modeling to study estragole bioactivation and detoxification in humans as compared with male rats. | 2009 Aug |
|
| Study of the metabolism of estragole in humans consuming fennel tea. | 2009 Dec |
|
| Insecticidal activity of basil oil, trans-anethole, estragole, and linalool to adult fruit flies of Ceratitis capitata, Bactrocera dorsalis, and Bactrocera cucurbitae. | 2009 Feb |
|
| Characterization of volatile substances in apples from Rosaceae family by headspace solid-phase microextraction followed by GC-qMS. | 2009 Jun |
|
| Determination of alkenylbenzenes and related flavour compounds in food samples by on-column preconcentration-capillary liquid chromatography. | 2009 Oct 23 |
|
| QCM-arrays for sensing terpenes in fresh and dried herbs via bio-mimetic MIP layers. | 2010 |
|
| Volatile compounds from Tagetes pusilla (Asteraceae) collected from the Venezuela Andes. | 2010 Aug |
|
| Ocimum sanctum essential oil and its active principles exert their antifungal activity by disrupting ergosterol biosynthesis and membrane integrity. | 2010 Dec |
|
| Volatile constituents and biological activities of Pycnostachys abyssinica and Pycnostachys eminii extracts. | 2010 Dec |
|
| Foeniculum vulgare essential oils: chemical composition, antioxidant and antimicrobial activities. | 2010 Feb |
|
| Risk assessment of consumption of methylchavicol and tarragon: the genotoxic potential in vivo and in vitro. | 2010 Feb |
|
| Ocimum sanctum Linn. A reservoir plant for therapeutic applications: An overview. | 2010 Jan |
|
| Predicting the hepatocarcinogenic potential of alkenylbenzene flavoring agents using toxicogenomics and machine learning. | 2010 Mar 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 Mar-Apr |
|
| Chemical composition of the essential oil of Feronia elephantum Correa. | 2010 Nov |
|
| Sphaeranthus indicus Linn.: A phytopharmacological review. | 2010 Oct |
|
| Enhancement of the Norfloxacin Antibiotic Activity by Gaseous Contact with the Essential Oil of Croton zehntneri. | 2010 Oct |
|
| Toxicology and carcinogenesis studies of isoeugenol (CAS No. 97-54-1) in F344/N rats and B6C3F1 mice (gavage studies). | 2010 Sep |
|
| Volatile fraction of lavender and bitter fennel infusion extracts. | 2010 Sep |
|
| Possible involvement of genotoxic mechanisms in estragole-induced hepatocarcinogenesis in rats. | 2012 Oct |
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
on
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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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DTXSID0020575
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140-67-0
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404113
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PARENT -> CONSTITUENT MAY BE PRESENT |
ASSAY (GC)
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PARENT -> CONSTITUENT ALWAYS PRESENT |
ASSAY (GC)
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PARENT -> CONSTITUENT MAY BE PRESENT |
ASSAY (GC)
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