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
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
| Molecular Formula | C8H10O3 |
| Molecular Weight | 154.1632 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
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| Phenyl propenoic side chain degradation of ferulic acid by Pycnoporus cinnabarinus - elucidation of metabolic pathways using [5-2H]-ferulic acid. | 2001 Feb 23 |
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| Rerouting the plant phenylpropanoid pathway by expression of a novel bacterial enoyl-CoA hydratase/lyase enzyme function. | 2001 Jul |
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| Enzymatic synthesis of vanillin. | 2001 Jun |
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| Redox properties of vanillyl-alcohol oxidase. | 2002 |
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| Inhibitory actions of several natural products on proliferation of rat vascular smooth muscle cells induced by Hsp60 from Chlamydia pneumoniae J138. | 2004 Oct 6 |
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| Posttraumatic epilepsy with special emphasis on prophylaxis and prevention. | 2005 |
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| Electrooxidation of vanillyl alcohol in acidic aqueous solution using rotating ring-disk electrode voltammetry. | 2005 Apr |
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| Synomone or kairomone?--Bulbophyllum apertum flower releases raspberry ketone to attract Bactrocera fruit flies. | 2005 Mar |
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| Transportation mechanism for vanillin uptake through fungal plasma membrane. | 2005 Sep |
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| Anti-inflammatory action of phenolic compounds from Gastrodia elata root. | 2006 Oct |
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| Multisensor system for determination of polyoxometalates containing vanadium at its different oxidation states. | 2007 Apr 30 |
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| Determination of gastrodin and vanillyl alcohol in Gastrodia elata Blume by pressurized liquid extraction at room temperature. | 2007 Aug |
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| Development and validation of an RP-HPLC method for quantitative determination of vanillin and related phenolic compounds in Vanilla planifolia. | 2007 Jan |
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| Chemiluminometric determination of vanillin in commercial vanillin products. | 2007 Jan 15 |
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| Reduction of carboxylic acids by Nocardia aldehyde oxidoreductase requires a phosphopantetheinylated enzyme. | 2007 Jan 5 |
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| Studies of the toxicological potential of capsinoids: X. Safety assessment and pharmacokinetics of capsinoids in healthy male volunteers after a single oral ingestion of CH-19 Sweet extract. | 2008 |
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| A constructed alkaline consortium and its dynamics in treating alkaline black liquor with very high pollution load. | 2008 |
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| 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 |
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| Evaluation of the extraction efficiency of thermally labile bioactive compounds in Gastrodia elata Blume by pressurized hot water extraction and microwave-assisted extraction. | 2008 Feb 22 |
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| The growing VAO flavoprotein family. | 2008 Jun 15 |
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| Discovery and characterization of a putrescine oxidase from Rhodococcus erythropolis NCIMB 11540. | 2008 Mar |
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| Protective effect of vanilloids against tert-butyl hydroperoxide-induced oxidative stress in vero cells culture. | 2008 May 28 |
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| Anti-angiogenic, anti-inflammatory and anti-nociceptive activities of vanillyl alcohol. | 2008 Oct |
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| Covalent flavinylation of vanillyl-alcohol oxidase is an autocatalytic process. | 2008 Oct |
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| A ternary complex of hydroxycinnamoyl-CoA hydratase-lyase (HCHL) with acetyl-CoA and vanillin gives insights into substrate specificity and mechanism. | 2008 Sep 1 |
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| New oxidase from Bjerkandera arthroconidial anamorph that oxidizes both phenolic and nonphenolic benzyl alcohols. | 2009 Apr |
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| Vanillin suppresses metastatic potential of human cancer cells through PI3K inhibition and decreases angiogenesis in vivo. | 2009 Apr 22 |
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| Identification of a gatekeeper residue that prevents dehydrogenases from acting as oxidases. | 2009 Feb 13 |
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| EMMA 2--a MAGE-compliant system for the collaborative analysis and integration of microarray data. | 2009 Feb 6 |
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| Export of functional Streptomyces coelicolor alditol oxidase to the periplasm or cell surface of Escherichia coli and its application in whole-cell biocatalysis. | 2009 Jun |
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| Cellulosic hydrolysate toxicity and tolerance mechanisms in Escherichia coli. | 2009 Oct 15 |
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| 4-Hydroxy-meth-yl-2-methoxy-phenol. | 2009 Oct 23 |
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| Functional loss of pAMT results in biosynthesis of capsinoids, capsaicinoid analogs, in Capsicum annuum cv. CH-19 Sweet. | 2009 Sep |
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| Production of recombinant cholesterol oxidase containing covalently bound FAD in Escherichia coli. | 2010 Apr 21 |
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| Effects of capsinoid ingestion on energy expenditure and lipid oxidation at rest and during exercise. | 2010 Aug 3 |
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| Anti-asthmatic activity of phenolic compounds from the roots of Gastrodia elata Bl. | 2010 Feb |
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| Methyl 3,5-bis-[(4-hydroxy-methyl-2-methoxy-phen-oxy)meth-yl]benzoate. | 2010 Feb 27 |
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| Novel phenolic glycosides, adenophorasides A-E, from Adenophora roots. | 2010 Jul |
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| Studies of the toxicological potential of capsinoids, XII: pharmacokinetic study of capsinoid-containing CH-19 Sweet extract in rats. | 2010 Mar |
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| Studies of the toxicological potential of capsinoids, XI: pharmacokinetic and tissue distribution study of 14C-dihydrocapsiate and metabolites in rats. | 2010 Mar |
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| Improved vanillin production in baker's yeast through in silico design. | 2010 Nov 8 |
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| Effects of dihydrocapsiate on adaptive and diet-induced thermogenesis with a high protein very low calorie diet: a randomized control trial. | 2010 Oct 6 |
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| The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket. | 2011 Feb 8 |
Sample Use Guides
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:51:58 GMT 2023
by
admin
on
Fri Dec 15 17:51:58 GMT 2023
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| Record UNII |
X7EA1JUA6M
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| Record Status |
Validated (UNII)
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| Record Version |
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JECFA EVALUATION |
VANILLYL ALCOHOL
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VANILLYL ALCOHOL
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