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=CC(CO)=CC=C1O
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 |
|---|---|---|
| The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket. | 2011-02-08 |
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| Improved vanillin production in baker's yeast through in silico design. | 2010-11-08 |
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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. | 2010-10-06 |
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| Effects of capsinoid ingestion on energy expenditure and lipid oxidation at rest and during exercise. | 2010-08-03 |
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| Novel phenolic glycosides, adenophorasides A-E, from Adenophora roots. | 2010-07 |
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| Production of recombinant cholesterol oxidase containing covalently bound FAD in Escherichia coli. | 2010-04-21 |
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| Studies of the toxicological potential of capsinoids, XII: pharmacokinetic study of capsinoid-containing CH-19 Sweet extract in rats. | 2010-03 |
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| Studies of the toxicological potential of capsinoids, XI: pharmacokinetic and tissue distribution study of 14C-dihydrocapsiate and metabolites in rats. | 2010-03 |
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| Methyl 3,5-bis-[(4-hydroxy-methyl-2-methoxy-phen-oxy)meth-yl]benzoate. | 2010-02-27 |
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| Anti-asthmatic activity of phenolic compounds from the roots of Gastrodia elata Bl. | 2010-02 |
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| 4-Hydroxy-meth-yl-2-methoxy-phenol. | 2009-10-23 |
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| Cellulosic hydrolysate toxicity and tolerance mechanisms in Escherichia coli. | 2009-10-15 |
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| Functional loss of pAMT results in biosynthesis of capsinoids, capsaicinoid analogs, in Capsicum annuum cv. CH-19 Sweet. | 2009-09 |
|
| Export of functional Streptomyces coelicolor alditol oxidase to the periplasm or cell surface of Escherichia coli and its application in whole-cell biocatalysis. | 2009-06 |
|
| Vanillin suppresses metastatic potential of human cancer cells through PI3K inhibition and decreases angiogenesis in vivo. | 2009-04-22 |
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| New oxidase from Bjerkandera arthroconidial anamorph that oxidizes both phenolic and nonphenolic benzyl alcohols. | 2009-04 |
|
| Identification of a gatekeeper residue that prevents dehydrogenases from acting as oxidases. | 2009-02-13 |
|
| EMMA 2--a MAGE-compliant system for the collaborative analysis and integration of microarray data. | 2009-02-06 |
|
| Anti-angiogenic, anti-inflammatory and anti-nociceptive activities of vanillyl alcohol. | 2008-10 |
|
| Covalent flavinylation of vanillyl-alcohol oxidase is an autocatalytic process. | 2008-10 |
|
| A ternary complex of hydroxycinnamoyl-CoA hydratase-lyase (HCHL) with acetyl-CoA and vanillin gives insights into substrate specificity and mechanism. | 2008-09-01 |
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| The growing VAO flavoprotein family. | 2008-06-15 |
|
| Protective effect of vanilloids against tert-butyl hydroperoxide-induced oxidative stress in vero cells culture. | 2008-05-28 |
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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. | 2008-04-15 |
|
| Discovery and characterization of a putrescine oxidase from Rhodococcus erythropolis NCIMB 11540. | 2008-03 |
|
| Evaluation of the extraction efficiency of thermally labile bioactive compounds in Gastrodia elata Blume by pressurized hot water extraction and microwave-assisted extraction. | 2008-02-22 |
|
| Structural analysis of the catalytic mechanism and stereoselectivity in Streptomyces coelicolor alditol oxidase. | 2008-01-22 |
|
| 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 |
|
| A constructed alkaline consortium and its dynamics in treating alkaline black liquor with very high pollution load. | 2008 |
|
| CoryneRegNet 4.0 - A reference database for corynebacterial gene regulatory networks. | 2007-11-06 |
|
| Protective effects of several components of Gastrodia elata on lipid peroxidation in gerbil brain homogenates. | 2007-10 |
|
| Studies on the antioxidant activities of natural vanilla extract and its constituent compounds through in vitro models. | 2007-09-19 |
|
| Determination of gastrodin and vanillyl alcohol in Gastrodia elata Blume by pressurized liquid extraction at room temperature. | 2007-08 |
|
| Discovery of a eugenol oxidase from Rhodococcus sp. strain RHA1. | 2007-05 |
|
| Multisensor system for determination of polyoxometalates containing vanadium at its different oxidation states. | 2007-04-30 |
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| Vanillin production using metabolically engineered Escherichia coli under non-growing conditions. | 2007-04-16 |
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| Chemiluminometric determination of vanillin in commercial vanillin products. | 2007-01-15 |
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| Reduction of carboxylic acids by Nocardia aldehyde oxidoreductase requires a phosphopantetheinylated enzyme. | 2007-01-05 |
|
| Development and validation of an RP-HPLC method for quantitative determination of vanillin and related phenolic compounds in Vanilla planifolia. | 2007-01 |
|
| Under the influence of the active deodorant ingredient 4-hydroxy-3-methoxybenzyl alcohol, the skin bacterium Corynebacterium jeikeium moderately responds with differential gene expression. | 2006-12-15 |
|
| Improving the performance of a quadrupole time-of-flight instrument for macromolecular mass spectrometry. | 2006-11-01 |
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| Phenols and lignans from Chenopodium album. | 2006-10-06 |
|
| Anti-inflammatory action of phenolic compounds from Gastrodia elata root. | 2006-10 |
|
| Potential of Rhodococcus strains for biotechnological vanillin production from ferulic acid and eugenol. | 2006-10 |
|
| Harnessing eugenol as a substrate for production of aromatic compounds with recombinant strains of Amycolatopsis sp. HR167. | 2006-09-18 |
|
| Characterization of four Rhodococcus alcohol dehydrogenase genes responsible for the oxidation of aromatic alcohols. | 2006-08 |
|
| Capsinoid is biosynthesized from phenylalanine and valine in a non-pungent pepper, Capsicum annuum L. cv. CH-19 sweet. | 2006-06 |
|
| Colorimetric evaluation of phenolic content and GC-MS characterization of phenolic composition of alimentary and cosmetic argan oil and press cake. | 2005-11-16 |
|
| Protective effect of capsinoid on lipid peroxidation in rat tissues induced by Fe-NTA. | 2005-11 |
|
| Crystal structures and inhibitor binding in the octameric flavoenzyme vanillyl-alcohol oxidase: the shape of the active-site cavity controls substrate specificity. | 1997-07-15 |
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
Mon Mar 31 18:55:35 GMT 2025
by
admin
on
Mon Mar 31 18:55:35 GMT 2025
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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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