U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of ESTRAGOLE

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

HIDE SMILES / InChI

Molecular Formula C10H12O
Molecular Weight 148.2017
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.337 µM [IC50]
3.2 mM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
In the peritonitis model, Estragole (500 and 750 mg/kg) decreased the infiltration of peritoneal exudate leukocytes.
Route of Administration: Oral
In Vitro Use Guide
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
Record UNII
9NIW07V3ET
Record Status Validated (UNII)
Record Version