VANILLYL ALCOHOL

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C8H10O3
Molecular Weight	154.1632
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(O)C=CC(CO)=C1

InChI

InChIKey=ZENOXNGFMSCLLL-UHFFFAOYSA-N

InChI=1S/C8H10O3/c1-11-8-4-6(5-9)2-3-7(8)10/h2-4,9-10H,5H2,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:18353 | https://www.ncbi.nlm.nih.gov/pubmed/28586214 | https://www.ncbi.nlm.nih.gov/pubmed/21705974

Vanillyl alcohol is a monomethoxybenzene that is 2-methoxyphenol substituted by a hydroxymethyl group at position 4. It has a role as a plant metabolite. It is a member of guaiacols and a member of benzyl alcohols. Vanillyl alcohol is a phenolic alcohol and is used as a flavoring agent in foods and beverages. Vanillyl alcohol effectively inhibited the cytotoxicity and improved cell viability in MPP+-induced MN9D dopaminergic cells. Vanillyl alcohol attenuated the elevation of reactive oxygen species (ROS) levels, decreased in the Bax/Bcl-2 ratio and poly (ADP-ribose) polymerase proteolysis. These results indicate that vanillyl alcohol protected dopaminergic MN9D cells against MPP+-induced apoptosis by relieving oxidative stress and modulating the apoptotic process and is therefore a potential candidate for treatment of neurodegenerative diseases such as Parkinson's disease.

Approval Year

PubMed

Title	Date	PubMed
Crystal structures and inhibitor binding in the octameric flavoenzyme vanillyl-alcohol oxidase: the shape of the active-site cavity controls substrate specificity.	1997 Jul 15	9261083
Tuning of the product spectrum of vanillyl-alcohol oxidase by medium engineering.	2001 Aug 17	11513884
Phenyl propenoic side chain degradation of ferulic acid by Pycnoporus cinnabarinus - elucidation of metabolic pathways using [5-2H]-ferulic acid.	2001 Feb 23	11173097
Determination of the active ingredients in Gastrodia rhizoma by capillary electrophoresis with electrochemical detection.	2001 Sep	11592643
Redox properties of vanillyl-alcohol oxidase.	2002	12078493
Enzymatic synthesis of a capsinoid by the acylation of vanillyl alcohol with fatty acid derivatives catalyzed by lipases.	2002 Feb	11999404
Cytotoxic terpenoid and immunosuppressive phenolic glycosides from the root bark of Dictamnus dasycarpus.	2002 May	12058319
Characterization of an extracellular salicyl alcohol oxidase from larval defensive secretions of Chrysomela populi and Phratora vitellinae (Chrysomelina).	2002 Nov	12530219
Cofactor-dependent assembly of the flavoenzyme vanillyl-alcohol oxidase.	2002 Sep 27	12107187
Non-pungent capsaicinoids from sweet pepper synthesis and evaluation of the chemopreventive and anticancer potential.	2003 Jan	12594536
On the mechanism of the laccase-mediator system in the oxidation of lignin.	2003 Nov 7	14613147
Analysis of the inhibition of food spoilage yeasts by vanillin.	2003 Sep 1	12892926
Structures of Michaelis and product complexes of plant cytokinin dehydrogenase: implications for flavoenzyme catalysis.	2004 Aug 27	15321719
Laboratory-evolved vanillyl-alcohol oxidase produces natural vanillin.	2004 Aug 6	15169773
Signal quenching, detoxification and mineralization of vir gene-inducing phenolics by the VirH2 protein of Agrobacterium tumefaciens.	2004 Feb	14763983
Inhibitory actions of several natural products on proliferation of rat vascular smooth muscle cells induced by Hsp60 from Chlamydia pneumoniae J138.	2004 Oct 6	15453708
Posttraumatic epilepsy with special emphasis on prophylaxis and prevention.	2005	15986723
Electrooxidation of vanillyl alcohol in acidic aqueous solution using rotating ring-disk electrode voltammetry.	2005 Apr	15844340
Synomone or kairomone?--Bulbophyllum apertum flower releases raspberry ketone to attract Bactrocera fruit flies.	2005 Mar	15898497
Protective effect of capsinoid on lipid peroxidation in rat tissues induced by Fe-NTA.	2005 Nov	16298741
Colorimetric evaluation of phenolic content and GC-MS characterization of phenolic composition of alimentary and cosmetic argan oil and press cake.	2005 Nov 16	16277411
Transportation mechanism for vanillin uptake through fungal plasma membrane.	2005 Sep	15868144
Characterization of four Rhodococcus alcohol dehydrogenase genes responsible for the oxidation of aromatic alcohols.	2006 Aug	16292529
Under the influence of the active deodorant ingredient 4-hydroxy-3-methoxybenzyl alcohol, the skin bacterium Corynebacterium jeikeium moderately responds with differential gene expression.	2006 Dec 15	16890319
Capsinoid is biosynthesized from phenylalanine and valine in a non-pungent pepper, Capsicum annuum L. cv. CH-19 sweet.	2006 Jun	16794338
Improving the performance of a quadrupole time-of-flight instrument for macromolecular mass spectrometry.	2006 Nov 1	17073415
Anti-inflammatory action of phenolic compounds from Gastrodia elata root.	2006 Oct	17121179
Potential of Rhodococcus strains for biotechnological vanillin production from ferulic acid and eugenol.	2006 Oct	16421716
Harnessing eugenol as a substrate for production of aromatic compounds with recombinant strains of Amycolatopsis sp. HR167.	2006 Sep 18	16677732
Phenols and lignans from Chenopodium album.	2006 Sep-Oct	17019936
Vanillin production using metabolically engineered Escherichia coli under non-growing conditions.	2007 Apr 16	17437627
Development and validation of an RP-HPLC method for quantitative determination of vanillin and related phenolic compounds in Vanilla planifolia.	2007 Jan	17313136
Reduction of carboxylic acids by Nocardia aldehyde oxidoreductase requires a phosphopantetheinylated enzyme.	2007 Jan 5	17102130
Discovery of a eugenol oxidase from Rhodococcus sp. strain RHA1.	2007 May	17419730
Genome-wide screening of the genes required for tolerance to vanillin, which is a potential inhibitor of bioethanol fermentation, in Saccharomyces cerevisiae.	2008 Apr 15	18471310
Protective effect of vanilloids against tert-butyl hydroperoxide-induced oxidative stress in vero cells culture.	2008 May 28	18439017
Covalent flavinylation of vanillyl-alcohol oxidase is an autocatalytic process.	2008 Oct	18793324
Vanillin suppresses metastatic potential of human cancer cells through PI3K inhibition and decreases angiogenesis in vivo.	2009 Apr 22	19368348
Anti-asthmatic activity of phenolic compounds from the roots of Gastrodia elata Bl.	2010 Feb	19874915
Improved vanillin production in baker's yeast through in silico design.	2010 Nov 8	21059201
The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.	2011 Feb 8	21142015

Patents

Sample Use Guides

In Vitro Use Guide

Vanillyl alcohol effectively inhibited the loss of cell viability in a dose-dependent manner according to the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay in MN9D dopaminergic cells. The viability of cells was increased to 51.5 ± 1.4%, 57.5 ± 2.8%, and 69.1 ± 3.1% when cells were pretreated with vanillyl alcohol at 1,10, and 20 uM, respectively. The DPPH radical scavenging activities of vanillyl alcohol at various concentrations (0.03, 0.06, 0.12, 0.25, 0.5 and 1 mg/mL) were 38.42, 76.08, 77.95, 78.16, 80.29, and 81.10%, respectively, with an IC50 value of 0.04 mg/mL. The alkyl radical scavenging activities of vanillyl alcohol (0.001, 0.003, 0.007, 0.015, 0.031 and 0.062 mg/mL) were 25.66, 41.25, 53.81, 78.88, 83.15, and 90.72%, respectively, with an IC50 value of 0.006 mg/mL.

Name

Type

Language

VANILLYL ALCOHOL

Systematic Name

English

NSC-3993

Code

English

VANILLIC ALCOHOL

Common Name

English

VANILLYL ALCOHOL [FHFI]

Common Name

English

4-HYDROXY-3-METHOXYBENZENEMETHANOL

Systematic Name

English

FEMA NO. 3737

Code

English

V0018

Code

English

4-HYDROXY-3-METHOXYBENZYL ALCOHOL

Systematic Name

English

V-0018

Code

English

Classification Tree Code System Code

JECFA EVALUATION

VANILLYL ALCOHOL