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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=CC(C=O)=CC=C1O

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

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

CNS Active
4002
Curator's Comment: A high oral dose caused central nervous system effects and coma in rats and rabbits

Originator

Hallman, M.|Twyman, G.
1
Curator's Comment: Ethyl vanillin was successfully synthetized by German Dr. M. Hallman and Dr. G. Twyman in 1874.

Approval Year

1961
146
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Agonist
2752
Blocker
555
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Conformational equilibria in vanillin and ethylvanillin.
2010-10-21
[Studies on the chemical constituents of marine sponge Iotrochota sp].
2010-04
Assessment of the anti-angiogenic, anti-inflammatory and antinociceptive properties of ethyl vanillin.
2010-02
Microencapsulation of flavors in carnauba wax.
2010
Compound-specific delta18O analyses of neutral sugars in soils using gas chromatography-pyrolysis-isotope ratio mass spectrometry: problems, possible solutions and a first application.
2009-11
Fast single run of vanilla fingerprint markers on microfluidic-electrochemistry chip for confirmation of common frauds.
2009-10
2-Eth-oxy-4-{[(2-nitro-phen-yl)hydrazono]meth-yl}phenol.
2009-09-30
2-Eth-oxy-4-[2-(3-nitro-phen-yl)-hydrazono-meth-yl]phenol.
2009-09-26
Methyl 4-(3-eth-oxy-4-hydroxy-phen-yl)-6-methyl-2-oxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate monohydrate.
2009-07-18
4-Hex-yloxy-3-methoxy-benzaldehyde.
2009-05-14
Intragastric administration of TRPV1, TRPV3, TRPM8, and TRPA1 agonists modulates autonomic thermoregulation in different manners in mice.
2009-05
4-(3-Eth-oxy-4-hydroxy-styr-yl)-1-methyl-pyridinium tosyl-ate monohydrate.
2008-12-10
3-Eth-oxy-4-hydroxy-benzaldehyde.
2008-09-24
Determination of phenolic compounds and hydroxymethylfurfural in meads using high performance liquid chromatography with coulometric-array and UV detection.
2008-08-15
Dihydroagarofuranoid sesquiterpenes, a lignan derivative, a benzenoid, and antitubercular constituents from the stem of Microtropis japonica.
2008-06
Rapid method for the determination of coumarin, vanillin, and ethyl vanillin in vanilla extract by reversed-phase liquid chromatography with ultraviolet detection.
2008-05-15
Competitive and noncompetitive odorant interactions in the early neural coding of odorant mixtures.
2008-03-05
Rapid sample screening method for authenticity controlling vanilla flavors using a CE microchip approach with electrochemical detection.
2007-11
Optimization of phenolic compounds analysis by capillary electrophoresis.
2007-06-15
Optical recording of the intrinsic signal from the human olfactory cleft.
2007-05
Determination of coumarin, vanillin, and ethyl vanillin in vanilla extract products: liquid chromatography mass spectrometry method development and validation studies.
2007-03-23
Chemiluminometric determination of vanillin in commercial vanillin products.
2007-01-15
Determination of vanillin and related flavor compounds in cocoa drink by capillary electrophoresis.
2007-01-05
Effect of flavors on the viscosity and gelling point of aqueous poloxamer solution.
2006-12
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006-11
Oregano, thyme and clove-derived flavors and skin sensitizers activate specific TRP channels.
2006-05
Electrophysiological and behavioral responses to chocolate volatiles in both sexes of the pyralid moths Ephestia cautella and Plodia interpunctella.
2005-12
Synthesis and non-aqueous medium titrations of some new 4-benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives.
2005-08-31
Improved malonaldehyde assay using headspace solid-phase microextraction and its application to the measurement of the antioxidant activity of phytochemicals.
2005-06-15
Structural basis for a broad but selective ligand spectrum of a mouse olfactory receptor: mapping the odorant-binding site.
2005-02-16
The effect of a glucocorticoid on olfactory response of isolated mouse olfactory cells.
2003-08-22
Qualitative determination of false-positive effects in the acetylcholinesterase assay using thin layer chromatography.
2003-06-10
Optimum methamphetamine profiling with sample preparation by solid-phase microextraction.
2002-09
Identification of impurities and statistical classification of methamphetamine tablets (Ya-Ba) seized in Thailand.
2002-04-18
Steroid hormone activity of flavonoids and related compounds.
2000-07
Patents

Patents

06924292
11
07674804
2
08034945
1
08349833
1
JP2002541123A
10
JPH07163380A
1

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 Mon Mar 31 17:33:44 GMT 2025
Edited
by admin
on Mon Mar 31 17:33:44 GMT 2025
Record UNII
YC9ST449YJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FEMA NO. 2464
Preferred Name English
ETHYL VANILLIN
FCC   FHFI   HSDB   II   INCI   MART.   MI   USP-RS   WHO-DD  
INCI  
Official Name English
3-Ethoxy-4-hydroxybenzaldehyde
Systematic Name English
ETHYL PROTOCATECHUIC ALDEHYDE
Common Name English
ETHYL VANILLIN [USP-RS]
Common Name 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
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
Created by admin on Mon Mar 31 17:33:44 GMT 2025 , Edited by admin on Mon Mar 31 17:33:44 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
204-464-7
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PRIMARY
HSDB
945
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PRIMARY
CHEBI
48408
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PRIMARY
RS_ITEM_NUM
1267500
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PRIMARY
ChEMBL
CHEMBL508676
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PRIMARY
DAILYMED
YC9ST449YJ
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PRIMARY
SMS_ID
100000079015
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PRIMARY
CAS
121-32-4
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PRIMARY
NCI_THESAURUS
C45678
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CONCEPT Industrial Aid
MESH
C045941
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PRIMARY
EVMPD
SUB13751MIG
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PRIMARY
NSC
1803
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PRIMARY
FDA UNII
YC9ST449YJ
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PRIMARY
EPA CompTox
DTXSID5021968
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PRIMARY
PUBCHEM
8467
Created by admin on Mon Mar 31 17:33:44 GMT 2025 , Edited by admin on Mon Mar 31 17:33:44 GMT 2025
PRIMARY
NCI_THESAURUS
C76709
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PRIMARY
RXCUI
1311571
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PRIMARY RxNorm
WIKIPEDIA
ETHYLVANILLIN
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PRIMARY
JECFA MONOGRAPH
776
Created by admin on Mon Mar 31 17:33:44 GMT 2025 , Edited by admin on Mon Mar 31 17:33:44 GMT 2025
PRIMARY
NSC
67240
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PRIMARY
MERCK INDEX
m5178
Created by admin on Mon Mar 31 17:33:44 GMT 2025 , Edited by admin on Mon Mar 31 17:33:44 GMT 2025
PRIMARY Merck Index
Related Record Type Details
Structure of 3-ETHOXY-4-HYDROXYBENZOIC ACID
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URINE
NIH
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