Estragole

Estragole (4-Allylanisole) is a relatively nontoxic volatile terpenoid ether and major component of the essential oil from many plants. Estragole significantly triggers Apoptosis, suppresses LPS-induced intracellular ROS production. Estragole activats Nrf-2 and regulates NF-κB. Estragole has anti-toxoplasma, anti-inflammatory, anti-edema, antioxidant and immunomodulatory properties. Estragole blocks DRG neuron excitability. Estragole has improves gastric ulcer activity[1][2][3][4][5][6][7][8][9][10][11][12][13].

Product Specifications

CAS Number

[140-67-0]

Product Name Alternative

4-Allylanisole

UNSPSC

12352005

Hazard Statement

H227, H302, H315, H317, H319, H341, H351, H402, H412

Target

Apoptosis; Keap1-Nrf2; NF-κB; Parasite; Reactive Oxygen Species (ROS)

Type

Natural Products

Related Pathways

Anti-infection; Apoptosis; Immunology/Inflammation; Metabolic Enzyme/Protease; NF-κB

Applications

Neuroscience-Neuromodulation

Field of Research

Infection; Inflammation/Immunology; Neurological Disease

Assay Protocol

https://www.medchemexpress.com/estragole.html

Purity

99.90

Solubility

DMSO : 100 mg/mL (ultrasonic)

Smiles

C=CCC1=CC=C(OC)C=C1

Molecular Formula

C10H12O

Molecular Weight

148.20

Precautions

H227, H302, H315, H317, H319, H341, H351, H402, H412

References & Citations

[1]Leal-Cardoso JH, et al. Effects of estragole on the compound action potential of the rat sciatic nerve. Braz J Med Biol Res. 2004 Aug;37 (8) :1193-8.|[2]Oliveira CB, et al. Anti-Toxoplasma Activity of Estragole and Thymol in Murine Models of Congenital and Noncongenital Toxoplasmosis. J Parasitol. 2016 Jun;102 (3) :369-76.|[3]Lashkari A, et al. Evaluating the In vitro anti-cancer potential of estragole from the essential oil of Agastache foeniculum [Pursh.] Kuntze. Biocatalysis and Agricultural Biotechnology, 2020, 27: 101727.|[4]Martins C, et al. Estragole: a weak direct-acting food-borne genotoxin and potential carcinogen. Mutat Res. 2012 Aug 30;747 (1) :86-92.|[5]Roy A, et al. Estragole exhibits anti-inflammatory activity with the regulation of NF-κB and Nrf-2 signaling pathways in LPS-induced RAW 264.7 cells. Natural Product Sciences, 2018, 24 (1) : 13-20.|[6]Schulte-Hubbert R, et al. Estragole: DNA adduct formation in primary rat hepatocytes and genotoxic potential in HepG2-CYP1A2 cells. Toxicology. 2020 Nov;444:152566.|[7]Coêlho ML, et al. Cytotoxic and Antioxidant Properties of Natural Bioactive Monoterpenes Nerol, Estragole, and 3,7-Dimethyl-1-Octanol. Adv Pharmacol Pharm Sci. 2022 Nov 23;2022:8002766.|[8]Silva-Comar FM, et al. Effect of estragole on leukocyte behavior and phagocytic activity of macrophages. Evid Based Complement Alternat Med. 2014;2014:784689.|[9]Silva-Alves KS, et al. Estragole blocks neuronal excitability by direct inhibition of Na+ channels. Braz J Med Biol Res. 2013 Dec;46 (12) :1056-1063.|[10]Rodrigues LB, et al. Anti-inflammatory and antiedematogenic activity of the Ocimum basilicum essential oil and its main compound estragole: In vivo mouse models. Chem Biol Interact. 2016 Sep 25;257:14-25.|[11]Alves Júnior EB, et al. Estragole prevents gastric ulcers via cytoprotective, antioxidant and immunoregulatory mechanisms in animal models. Biomed Pharmacother. 2020 Oct;130:110578.|[12]Oliveira CB, et al. Anti-Toxoplasma Activity of Estragole and Thymol in Murine Models of Congenital and Noncongenital Toxoplasmosis. J Parasitol. 2016 Jun;102 (3) :369-76.|[13]Kaledin VI, et al. 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. Biofizika. 2010 Mar-Apr;55 (2) :326-35. Russian.