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Details

Stereochemistry ACHIRAL
Molecular Formula C9H10O3
Molecular Weight 166.1739
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ETHYL VANILLIN

SMILES

CCOC1=C(O)C=CC(C=O)=C1

InChI

InChIKey=CBOQJANXLMLOSS-UHFFFAOYSA-N
InChI=1S/C9H10O3/c1-2-12-9-5-7(6-10)3-4-8(9)11/h3-6,11H,2H2,1H3

HIDE SMILES / InChI

Molecular Formula C9H10O3
Molecular Weight 166.1739
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

Ethyl vanillin is an important food additive and flavouring agent approved by FAO/WHO, has a vanilla odor four times that of vanillin and shows anti-mutagenic activity. It is used as flavoring agent and/or as an additive by the food, cosmetic, or pharmaceutic industries. Ethyl vanillin possesses antioxidant and anti-inflammatory properties. The antioxidant activity of ethyl vanillin was much stronger than that of vanillin in the oxidative hemolysis inhibition assay, but was the same as that of vanillin in the ORAC assay. Oral administration of ethyl vanillin to mice increased the concentration of ethyl vanillic acid, and effectively raised antioxidant activity in the plasma as compared to the effect of vanillin. The antioxidant activity of ethyl vanillin might be more beneficial than has been thought in daily health practice. The anti-angiogenic, anti-inflammatory and anti-nociceptive properties of EVA are based on its suppressive effect on the production of nitric oxide possibly via decreasing the reactive oxygen species level.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Mice were given 32.7 mg/kg of ethyl vanillin orally.
Route of Administration: Oral
In Vitro Use Guide
Authors transfected clonal COS-7 cells with full-length mouse TRPA1 C-terminally fused to GFP (TRPA1-GFP) and exposed them to EVA (3 mM) and AITC (300 uM). EVA and AITC only activated transfected (GFP+) cells, showing that wild type COS-7 cells lack endogenous TRPA1 and other potential EVA-induced calcium influx pathways such as TRPV3.
Substance Class Chemical
Record UNII
YC9ST449YJ
Record Status Validated (UNII)
Record Version