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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
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
3913
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
2678
Agonist
2678
Blocker
537
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Steroid hormone activity of flavonoids and related compounds.
2000 Jul
Optimum methamphetamine profiling with sample preparation by solid-phase microextraction.
2002 Sep
The effect of a glucocorticoid on olfactory response of isolated mouse olfactory cells.
2003 Jul-Aug
Qualitative determination of false-positive effects in the acetylcholinesterase assay using thin layer chromatography.
2003 May-Jun
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
Structural basis for a broad but selective ligand spectrum of a mouse olfactory receptor: mapping the odorant-binding site.
2005 Feb 16
Improved malonaldehyde assay using headspace solid-phase microextraction and its application to the measurement of the antioxidant activity of phytochemicals.
2005 Jun 15
Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods.
2006 Nov
Chemiluminometric determination of vanillin in commercial vanillin products.
2007 Jan 15
Optimization of phenolic compounds analysis by capillary electrophoresis.
2007 Jun 15
Determination of coumarin, vanillin, and ethyl vanillin in vanilla extract products: liquid chromatography mass spectrometry method development and validation studies.
2007 Mar 23
Optical recording of the intrinsic signal from the human olfactory cleft.
2007 May
Rapid sample screening method for authenticity controlling vanilla flavors using a CE microchip approach with electrochemical detection.
2007 Nov
Determination of phenolic compounds and hydroxymethylfurfural in meads using high performance liquid chromatography with coulometric-array and UV detection.
2008 Aug 15
4-(3-Eth-oxy-4-hydroxy-styr-yl)-1-methyl-pyridinium tosyl-ate monohydrate.
2008 Dec 10
Dihydroagarofuranoid sesquiterpenes, a lignan derivative, a benzenoid, and antitubercular constituents from the stem of Microtropis japonica.
2008 Jun
Competitive and noncompetitive odorant interactions in the early neural coding of odorant mixtures.
2008 Mar 5
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
3-Eth-oxy-4-hydroxy-benzaldehyde.
2008 Sep 24
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 Jul 18
Intragastric administration of TRPV1, TRPV3, TRPM8, and TRPA1 agonists modulates autonomic thermoregulation in different manners in mice.
2009 May
4-Hex-yloxy-3-methoxy-benzaldehyde.
2009 May 14
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 Nov
Fast single run of vanilla fingerprint markers on microfluidic-electrochemistry chip for confirmation of common frauds.
2009 Oct
2-Eth-oxy-4-[2-(3-nitro-phen-yl)-hydrazono-meth-yl]phenol.
2009 Sep 26
2-Eth-oxy-4-{[(2-nitro-phen-yl)hydrazono]meth-yl}phenol.
2009 Sep 30
Microencapsulation of flavors in carnauba wax.
2010
[Studies on the chemical constituents of marine sponge Iotrochota sp].
2010 Apr
Assessment of the anti-angiogenic, anti-inflammatory and antinociceptive properties of ethyl vanillin.
2010 Feb
Conformational equilibria in vanillin and ethylvanillin.
2010 Oct 21
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 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
  • Download
Name Type Language
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
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
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
204-464-7
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
HSDB
945
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
CHEBI
48408
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PRIMARY
RS_ITEM_NUM
1267500
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
ChEMBL
CHEMBL508676
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
DAILYMED
YC9ST449YJ
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
SMS_ID
100000079015
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
CAS
121-32-4
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
NCI_THESAURUS
C45678
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
CONCEPT Industrial Aid
MESH
C045941
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
EVMPD
SUB13751MIG
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
NSC
1803
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
FDA UNII
YC9ST449YJ
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID5021968
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
PUBCHEM
8467
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
NCI_THESAURUS
C76709
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
RXCUI
1311571
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY RxNorm
WIKIPEDIA
ETHYLVANILLIN
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
JECFA MONOGRAPH
776
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
NSC
67240
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY
MERCK INDEX
m5178
Created by admin on Fri Dec 15 14:58:43 GMT 2023 , Edited by admin on Fri Dec 15 14:58:43 GMT 2023
PRIMARY Merck Index
Related Record Type Details
Structure of 3-ETHOXY-4-HYDROXYBENZOIC ACID
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URINE
NIH
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