ETHYL VANILLIN

Possibly Marketed Outside US

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 Search

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25344384 | https://www.ncbi.nlm.nih.gov/pubmed/22146718 | https://www.ncbi.nlm.nih.gov/pubmed/21201206 | https://www.ncbi.nlm.nih.gov/pubmed/20195833

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 Target	Pharmacology	Condition	Potency
Transient receptor potential cation channel subfamily A member 1 38 Target ID: CHEMBL1075310 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28620120	Agonist 2678
Transient receptor potential cation channel subfamily V member 3 12 Target ID: CHEMBL5522 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28620120 \| https://www.ncbi.nlm.nih.gov/pubmed/26843581	Agonist 2678
Voltage-gated L-type calcium channel 92 Target ID: CHEMBL2095229 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25344384	Blocker 537
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22146718	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20195833	Primary		Preclinical	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20195833	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Identification of impurities and statistical classification of methamphetamine tablets (Ya-Ba) seized in Thailand.	2002 Apr 18	12084485
The effect of a glucocorticoid on olfactory response of isolated mouse olfactory cells.	2003 Jul-Aug	12929589
Synthesis and non-aqueous medium titrations of some new 4-benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives.	2005 Aug 31	18007364
Oregano, thyme and clove-derived flavors and skin sensitizers activate specific TRP channels.	2006 May	16617338
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.	2006 Nov	16497524
Rapid sample screening method for authenticity controlling vanilla flavors using a CE microchip approach with electrochemical detection.	2007 Nov	17941116
Rapid method for the determination of coumarin, vanillin, and ethyl vanillin in vanilla extract by reversed-phase liquid chromatography with ultraviolet detection.	2008 Mar-Apr	18476352
3-Eth-oxy-4-hydroxy-benzaldehyde.	2008 Sep 24	21201206
2-Eth-oxy-4-[2-(3-nitro-phen-yl)-hydrazono-meth-yl]phenol.	2009 Sep 26	21577980
2-Eth-oxy-4-{[(2-nitro-phen-yl)hydrazono]meth-yl}phenol.	2009 Sep 30	21578012
[Studies on the chemical constituents of marine sponge Iotrochota sp].	2010 Apr	20845780

Patents

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 Created by `admin` on `Fri Dec 15 14:58:43 GMT 2023` Edited by `admin` on `Fri Dec 15 14:58:43 GMT 2023`
Record UNII	YC9ST449YJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHYL VANILLIN

Official Name

English

3-Ethoxy-4-hydroxybenzaldehyde

Systematic Name

English

ETHYL PROTOCATECHUIC ALDEHYDE

Common Name

English

ETHYL VANILLIN [USP-RS]

Common Name

English

FEMA NO. 2464

Code

English

AROVANILLON

Common Name

English

RHODIAROME

Common Name

English

ETHYL VANILLIN [MI]

Common Name

English

VANILLAL

Common Name

English

NSC-1803

Code

English

ETHYL VANILLIN [FHFI]

Common Name

English

ETHYL VANILLIN [II]

Common Name

English

BENZALDEHYDE, 3-ETHOXY-4-HYDROXY-

Systematic Name

English

ETHYL VANILLIN [HSDB]

Common Name

English

ETHYL VANILLIN [FCC]

Common Name

English

ETHYLVANILLIN

Systematic Name

English

J2.006K

Code

English

PROTOCATECHUIC ALDEHYDE ETHYL ETHER

Common Name

English

ETHYL VANILLIN [INCI]

Common Name

English

NSC-67240

Code

English

ETHYL VANILLIN [MART.]

Common Name

English

VANILLIN,ETHYL [VANDF]

Common Name

English

4-HYDROXY-3-ETHOXYBENZALDEHYDE

Systematic Name

English

Ethyl vanillin [WHO-DD]

Common Name

English

Classification Tree Code System Code

JECFA EVALUATION

ETHYL VANILLIN