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498-00-0,MFCD00004659
Catalog No.:AA003LF4

498-00-0 | 4-Hydroxy-3-methoxybenzyl alcohol

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  • Technical Information
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Technical Information
Catalog Number:
AA003LF4
Chemical Name:
4-Hydroxy-3-methoxybenzyl alcohol
CAS Number:
498-00-0
Molecular Formula:
C8H10O3
Molecular Weight:
154.1632
MDL Number:
MFCD00004659
SMILES:
COc1cc(CO)ccc1O
NSC Number:
3993
FEMA Number:
3737
Properties
Properties
 
BP:
313.1°C at 760 mmHg  
Form:
Solid  
MP:
110-117 °C(lit.)  
Refractive Index:
1.4620 (estimate)  
Storage:
Inert atmosphere;Room Temperature;  

Computed Properties
 
Complexity:
116  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
11  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
2  

Literature

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Journal: Current microbiology 20121201

Title: Novel glycoside of vanillyl alcohol, 4-hydroxy-3-methoxybenzyl-α-D-glucopyranoside: study of enzymatic synthesis, in vitro digestion and antioxidant activity.

Journal: Bioprocess and biosystems engineering 20120901

Title: Hot or not? Discovery and characterization of a thermostable alditol oxidase from Acidothermus cellulolyticus 11B.

Journal: Applied microbiology and biotechnology 20120701

Title: Two decades of studying non-covalent biomolecular assemblies by means of electrospray ionization mass spectrometry.

Journal: Journal of the Royal Society, Interface 20120507

Title: Glycosylation of vanillin and 8-nordihydrocapsaicin by cultured Eucalyptus perriniana cells.

Journal: Molecules (Basel, Switzerland) 20120502

Title: Decarboxylation of ferulic acid to 4-vinyl guaiacol by Streptomyces setonii.

Journal: Applied biochemistry and biotechnology 20120101

Title: Essential oils in food preservation: mode of action, synergies, and interactions with food matrix components.

Journal: Frontiers in microbiology 20120101

Title: Effects of acidic polysaccharides from gastrodia rhizome on systolic blood pressure and serum lipid concentrations in spontaneously hypertensive rats fed a high-fat diet.

Journal: International journal of molecular sciences 20120101

Title: Acidic polysaccharide extracts from Gastrodia Rhizomes suppress the atherosclerosis risk index through inhibition of the serum cholesterol composition in Sprague Dawley rats fed a high-fat diet.

Journal: International journal of molecular sciences 20120101

Title: The genome of Ganoderma lucidum provides insights into triterpenes biosynthesis and wood degradation [corrected].

Journal: PloS one 20120101

Title: Effects of alcohol compounds on the growth and lipid accumulation of oleaginous yeast Trichosporon fermentans.

Journal: PloS one 20120101

Title: Ethnobotanical survey, chemical composition, and antioxidant capacity of methanolic extract of the root bark of Annona cuneata Oliv.

Journal: Journal of medicinal food 20111101

Title: Environmental effects on the lignin model monomer, vanillyl alcohol, studied by Raman spectroscopy.

Journal: The journal of physical chemistry. B 20111006

Title: Shorter and modular synthesis of hemicryptophane-tren derivatives.

Journal: Organic letters 20110715

Title: Enzymatic synthesis of lipophilic rutin and vanillyl esters from fish byproducts.

Journal: Journal of agricultural and food chemistry 20110713

Title: The crystal structure and mechanism of an unusual oxidoreductase, GilR, involved in gilvocarcin V biosynthesis.

Journal: The Journal of biological chemistry 20110701

Title: Neuroprotective effects of vanillyl alcohol in Gastrodia elata Blume through suppression of oxidative stress and anti-apoptotic activity in toxin-induced dopaminergic MN9D cells.

Journal: Molecules (Basel, Switzerland) 20110624

Title: Galactonolactone oxidoreductase from Trypanosoma cruzi employs a FAD cofactor for the synthesis of vitamin C.

Journal: Biochimica et biophysica acta 20110501

Title: Gastrodia Elata Bl Attenuates Cocaine-Induced Conditioned Place Preference and Convulsion, but not Behavioral Sensitization in Mice: Importance of GABA(A) Receptors.

Journal: Current neuropharmacology 20110301

Title: Gastrodia elata bl attenuates methamphetamine-induced dopaminergic toxicity via inhibiting oxidative burdens.

Journal: Current neuropharmacology 20110301

Title: Effects of gastrodia elata bl on phencyclidine-induced schizophrenia-like psychosis in mice.

Journal: Current neuropharmacology 20110301

Title: The mouse eugenol odorant receptor: structural and functional plasticity of a broadly tuned odorant binding pocket.

Journal: Biochemistry 20110208

Title: Evaluation of the antioxidant activity of capsiate analogues in polar, nonpolar, and micellar media.

Journal: Journal of agricultural and food chemistry 20110126

Title: Phenylpropanoid glycoside analogues: enzymatic synthesis, antioxidant activity and theoretical study of their free radical scavenger mechanism.

Journal: PloS one 20110101

Title: Synthesis of stable isotope-labeled precursors for the biosyntheses of capsaicinoids, capsinoids, and capsiconinoids.

Journal: Bioscience, biotechnology, and biochemistry 20110101

Title: Isolation and characterization of novel bacterial strains exhibiting ligninolytic potential.

Journal: BMC biotechnology 20110101

Title: Chemical and transcriptional responses of Norway spruce genotypes with different susceptibility to Heterobasidion spp. infection.

Journal: BMC plant biology 20110101

Title: Antioxidant properties of ethyl vanillin in vitro and in vivo.

Journal: Bioscience, biotechnology, and biochemistry 20110101

Title: Novel phenolic glycosides, adenophorasides A-E, from Adenophora roots.

Journal: Journal of natural medicines 20100701

Title: Studies of the toxicological potential of capsinoids, XI: pharmacokinetic and tissue distribution study of 14C-dihydrocapsiate and metabolites in rats.

Journal: International journal of toxicology 20100301

Title: Studies of the toxicological potential of capsinoids, XII: pharmacokinetic study of capsinoid-containing CH-19 Sweet extract in rats.

Journal: International journal of toxicology 20100301

Title: Methyl 3,5-bis-[(4-hydroxy-methyl-2-methoxy-phen-oxy)meth-yl]benzoate.

Journal: Acta crystallographica. Section E, Structure reports online 20100301

Title: Anti-asthmatic activity of phenolic compounds from the roots of Gastrodia elata Bl.

Journal: International immunopharmacology 20100201

Title: Production of recombinant cholesterol oxidase containing covalently bound FAD in Escherichia coli.

Journal: BMC biotechnology 20100101

Title: Effects of capsinoid ingestion on energy expenditure and lipid oxidation at rest and during exercise.

Journal: Nutrition & metabolism 20100101

Title: Effects of dihydrocapsiate on adaptive and diet-induced thermogenesis with a high protein very low calorie diet: a randomized control trial.

Journal: Nutrition & metabolism 20100101

Title: Improved vanillin production in baker's yeast through in silico design.

Journal: Microbial cell factories 20100101

Title: 4-Hydroxy-meth-yl-2-methoxy-phenol.

Journal: Acta crystallographica. Section E, Structure reports online 20091101

Title: Functional loss of pAMT results in biosynthesis of capsinoids, capsaicinoid analogs, in Capsicum annuum cv. CH-19 Sweet.

Journal: The Plant journal : for cell and molecular biology 20090901

Title: Export of functional Streptomyces coelicolor alditol oxidase to the periplasm or cell surface of Escherichia coli and its application in whole-cell biocatalysis.

Journal: Applied microbiology and biotechnology 20090601

Title: Vanillin suppresses metastatic potential of human cancer cells through PI3K inhibition and decreases angiogenesis in vivo.

Journal: Journal of agricultural and food chemistry 20090422

Title: New oxidase from Bjerkandera arthroconidial anamorph that oxidizes both phenolic and nonphenolic benzyl alcohols.

Journal: Biochimica et biophysica acta 20090401

Title: Identification of a gatekeeper residue that prevents dehydrogenases from acting as oxidases.

Journal: The Journal of biological chemistry 20090213

Title: EMMA 2--a MAGE-compliant system for the collaborative analysis and integration of microarray data.

Journal: BMC bioinformatics 20090101

Title: Cellulosic hydrolysate toxicity and tolerance mechanisms in Escherichia coli.

Journal: Biotechnology for biofuels 20090101

Title: Covalent flavinylation of vanillyl-alcohol oxidase is an autocatalytic process.

Journal: The FEBS journal 20081001

Title: Anti-angiogenic, anti-inflammatory and anti-nociceptive activities of vanillyl alcohol.

Journal: Archives of pharmacal research 20081001

Title: A ternary complex of hydroxycinnamoyl-CoA hydratase-lyase (HCHL) with acetyl-CoA and vanillin gives insights into substrate specificity and mechanism.

Journal: The Biochemical journal 20080901

Title: The growing VAO flavoprotein family.

Journal: Archives of biochemistry and biophysics 20080615

Title: Protective effect of vanilloids against tert-butyl hydroperoxide-induced oxidative stress in vero cells culture.

Journal: Journal of agricultural and food chemistry 20080528

Title: Discovery and characterization of a putrescine oxidase from Rhodococcus erythropolis NCIMB 11540.

Journal: Applied microbiology and biotechnology 20080301

Title: Evaluation of the extraction efficiency of thermally labile bioactive compounds in Gastrodia elata Blume by pressurized hot water extraction and microwave-assisted extraction.

Journal: Journal of chromatography. A 20080222

Title: Structural analysis of the catalytic mechanism and stereoselectivity in Streptomyces coelicolor alditol oxidase.

Journal: Biochemistry 20080122

Title: Genome-wide screening of the genes required for tolerance to vanillin, which is a potential inhibitor of bioethanol fermentation, in Saccharomyces cerevisiae.

Journal: Biotechnology for biofuels 20080101

Title: A constructed alkaline consortium and its dynamics in treating alkaline black liquor with very high pollution load.

Journal: PloS one 20080101

Title: 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.

Journal: International journal of toxicology 20080101

Title: Protective effects of several components of Gastrodia elata on lipid peroxidation in gerbil brain homogenates.

Journal: Phytotherapy research : PTR 20071001

Title: Studies on the antioxidant activities of natural vanilla extract and its constituent compounds through in vitro models.

Journal: Journal of agricultural and food chemistry 20070919

Title: Determination of gastrodin and vanillyl alcohol in Gastrodia elata Blume by pressurized liquid extraction at room temperature.

Journal: Journal of separation science 20070801

Title: Discovery of a eugenol oxidase from Rhodococcus sp. strain RHA1.

Journal: The FEBS journal 20070501

Title: Multisensor system for determination of polyoxometalates containing vanadium at its different oxidation states.

Journal: Talanta 20070430

Title: Chemiluminometric determination of vanillin in commercial vanillin products.

Journal: Talanta 20070115

Title: Reduction of carboxylic acids by Nocardia aldehyde oxidoreductase requires a phosphopantetheinylated enzyme.

Journal: The Journal of biological chemistry 20070105

Title: Development and validation of an RP-HPLC method for quantitative determination of vanillin and related phenolic compounds in Vanilla planifolia.

Journal: Journal of separation science 20070101

Title: Vanillin production using metabolically engineered Escherichia coli under non-growing conditions.

Journal: Microbial cell factories 20070101

Title: CoryneRegNet 4.0 - A reference database for corynebacterial gene regulatory networks.

Journal: BMC bioinformatics 20070101

Title: Under the influence of the active deodorant ingredient 4-hydroxy-3-methoxybenzyl alcohol, the skin bacterium Corynebacterium jeikeium moderately responds with differential gene expression.

Journal: Journal of biotechnology 20061215

Title: Improving the performance of a quadrupole time-of-flight instrument for macromolecular mass spectrometry.

Journal: Analytical chemistry 20061101

Title: Potential of Rhodococcus strains for biotechnological vanillin production from ferulic acid and eugenol.

Journal: Applied microbiology and biotechnology 20061001

Title: Anti-inflammatory action of phenolic compounds from Gastrodia elata root.

Journal: Archives of pharmacal research 20061001

Title: Harnessing eugenol as a substrate for production of aromatic compounds with recombinant strains of Amycolatopsis sp. HR167.

Journal: Journal of biotechnology 20060918

Title: Characterization of four Rhodococcus alcohol dehydrogenase genes responsible for the oxidation of aromatic alcohols.

Journal: Applied microbiology and biotechnology 20060801

Title: Capsinoid is biosynthesized from phenylalanine and valine in a non-pungent pepper, Capsicum annuum L. cv. CH-19 sweet.

Journal: Bioscience, biotechnology, and biochemistry 20060601

Title: Phenols and lignans from Chenopodium album.

Journal: Phytochemical analysis : PCA 20060101

Title: Colorimetric evaluation of phenolic content and GC-MS characterization of phenolic composition of alimentary and cosmetic argan oil and press cake.

Journal: Journal of agricultural and food chemistry 20051116

Title: Protective effect of capsinoid on lipid peroxidation in rat tissues induced by Fe-NTA.

Journal: Free radical research 20051101

Title: Transportation mechanism for vanillin uptake through fungal plasma membrane.

Journal: Applied microbiology and biotechnology 20050901

Title: Electrooxidation of vanillyl alcohol in acidic aqueous solution using rotating ring-disk electrode voltammetry.

Journal: Analytical sciences : the international journal of the Japan Society for Analytical Chemistry 20050401

Title: Synomone or kairomone?--Bulbophyllum apertum flower releases raspberry ketone to attract Bactrocera fruit flies.

Journal: Journal of chemical ecology 20050301

Title: Posttraumatic epilepsy with special emphasis on prophylaxis and prevention.

Journal: Acta neurochirurgica. Supplement 20050101

Title: Inhibitory actions of several natural products on proliferation of rat vascular smooth muscle cells induced by Hsp60 from Chlamydia pneumoniae J138.

Journal: Journal of agricultural and food chemistry 20041006

Title: Structures of Michaelis and product complexes of plant cytokinin dehydrogenase: implications for flavoenzyme catalysis.

Journal: Journal of molecular biology 20040827

Title: Laboratory-evolved vanillyl-alcohol oxidase produces natural vanillin.

Journal: The Journal of biological chemistry 20040806

Title: Signal quenching, detoxification and mineralization of vir gene-inducing phenolics by the VirH2 protein of Agrobacterium tumefaciens.

Journal: Molecular microbiology 20040201

Title: On the mechanism of the laccase-mediator system in the oxidation of lignin.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20031107

Title: Analysis of the inhibition of food spoilage yeasts by vanillin.

Journal: International journal of food microbiology 20030901

Title: Non-pungent capsaicinoids from sweet pepper synthesis and evaluation of the chemopreventive and anticancer potential.

Journal: European journal of nutrition 20030101

Title: Characterization of an extracellular salicyl alcohol oxidase from larval defensive secretions of Chrysomela populi and Phratora vitellinae (Chrysomelina).

Journal: Insect biochemistry and molecular biology 20021101

Title: Cofactor-dependent assembly of the flavoenzyme vanillyl-alcohol oxidase.

Journal: The Journal of biological chemistry 20020927

Title: Cytotoxic terpenoid and immunosuppressive phenolic glycosides from the root bark of Dictamnus dasycarpus.

Journal: Planta medica 20020501

Title: Enzymatic synthesis of a capsinoid by the acylation of vanillyl alcohol with fatty acid derivatives catalyzed by lipases.

Journal: Bioscience, biotechnology, and biochemistry 20020201

Title: Redox properties of vanillyl-alcohol oxidase.

Journal: Methods in enzymology 20020101

Title: Determination of the active ingredients in Gastrodia rhizoma by capillary electrophoresis with electrochemical detection.

Journal: The Analyst 20010901

Title: Tuning of the product spectrum of vanillyl-alcohol oxidase by medium engineering.

Journal: FEBS letters 20010817

Title: Rerouting the plant phenylpropanoid pathway by expression of a novel bacterial enoyl-CoA hydratase/lyase enzyme function.

Journal: The Plant cell 20010701

Title: Enzymatic synthesis of vanillin.

Journal: Journal of agricultural and food chemistry 20010601

Title: Phenyl propenoic side chain degradation of ferulic acid by Pycnoporus cinnabarinus - elucidation of metabolic pathways using [5-2H]-ferulic acid.

Journal: Journal of biotechnology 20010223

Title: Crystal structures and inhibitor binding in the octameric flavoenzyme vanillyl-alcohol oxidase: the shape of the active-site cavity controls substrate specificity.

Journal: Structure (London, England : 1993) 19970715

Title: Chen Z, et al. Establishing an Artificial Pathway for De Novo Biosynthesis of Vanillyl Alcohol in Escherichia coli. ACS Synth Biol. 2017 Sep 15;6(9):1784-1792.

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Tags:498-00-0 Molecular Formula|498-00-0 MDL|498-00-0 SMILES|498-00-0 4-Hydroxy-3-methoxybenzyl alcohol