Under anaerobic conditions, the enzyme is easily reduced by vanillyl alcohol to the twoelectron reduced form. Vanillyl alcohol, also known as 3methoxy4hydroxybenzyl alcohol, comes from vanillin and is used to flavor food. Vanillin is a member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. Recommendation for orthovanillyl alcohol flavor usage levels up to. Vanillyl alcohol definition is a crystalline phenolic alcohol ch3oohc6h3ch2 obtained by reducing vanillin. Vanillyl alcohol 498000 buy and find out price and availability, msds, properties of tcis high quality specialty chemicals. Vanillyl alcohol c8h10o3 cid 62348 structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities. Preparation of vanillyl alcohol by sodium borohydride reduction introduction the purpose of this experiment is to prepare vanillylalcohol by means of a sodium borohydride reduction. Sonochemical oxidation of vanillyl alcohol to vanillin in. A0433vanillyl acetate the information in this msds was obtained from current and reliable sources.
Use water spray, alcoholresistant foam, dry chemical or carbon dioxide special hazards arising from the substance or mixture. Safety data sheet creation date 09jul2009 revision date 18jan2018 revision number 4 1. Hcl oh ho h 3co vanillin, 1 vanillyl alcohol, 2 4 3 either lialh4 and nabh4 could be used for this reduction, but sodium borohydride is the reagent of choice. In early organic chemistry reductions of ketones to alcohols were tough. These type of reactions were regularly performed with metallic sodium or with the process of catalytic hydrogenation over a platinum.
Predicted data is generated using the us environmental protection agencys episuite. The chromatographic conditions were optimized by means of computerassisted method development. However, the data is provided without any warranty, expressed or implied, regarding its correctness or accuracy. In this work, vanillyl alcohol was utilized as a promising ligninbased building block for the synthesis of epoxy monomers and resins. Box 697, osprey, florida, 342290697 941 3779935 fax 941 3779539 cas number 67630. Specifically, diglycyl ether of vanillyl alcohol dgeva was synthesized and its chemical structure was confirmed by 1 hnmr, cnmr, ftir, and gpc. Vanillylalcohol oxidase from byssochlamys fulva v107 was purified to apparent homogeneity as shown by sdspage and gelpermeation hplc. We provide cas 498000 msds, certificate of analysis references. Vanillyl alcohol, food and flavor ingredient, flavis no. Anticonvulsive and free radical scavenging activities of vanillyl alcohol in ferric chlorideinduced epileptic seizures in spraguedawley rats. A reduction is used in order to produce a variety of functional groups, such as, alcohols. It has a role as a plant metabolite, a flavouring agent, an antioxidant and an anticonvulsant.
First aid measures description of first aid measures. Vanillyl alcohol is a monomethoxybenzene that is 2methoxyphenol substituted by a hydroxymethyl group at position 4. Pdf vanillin, a promising biobased buildingblock for. First aid measures general advice consult a physician. The visible absorption spectrum of the oxidized enzyme shows maxima at 354 nm and 439 nm, and shoulders at 370, 417 and 461 nm. It is a member of phenols, a monomethoxybenzene and a member of benzaldehydes. One reagent lane fair lawn, nj 07410 for information in north america, call. If medical advice is needed, have product container or label at hand keep out of reach of children read label.
Parchem is open and ready to supply materials 18002823982 read more. Identification product name ethanol, anhydrous histological cat no. The oxidoreductases need cofactors that must be regenerated. Vanillyl alcohol definition of vanillyl alcohol by. Uses advised against not for food, drug, pesticide or biocidal product use. Microsoft powerpoint borohydride reduction of vanillin. Bimodal resin blends of diglycidyl ether of bisphenol a. Practical experience shows that this is most readily achieved by using living cells of microorganisms. Borohydride reduction of vanillin to vanillyl alcohol 28. Hold eyelids apart and flush eyes with plenty of water for at least 15 minutes. Ungraded products supplied by spectrum are indicative of a grade suitable for general industrial use or research purposes and typically are not suitable for. Inversion of stereospecificity of vanillylalcohol oxidase. Sds of vanillin acetate, safety data sheets, cas 881685.
It is a member of guaiacols and a member of benzyl alcohols. Safety data sheet according to 29cfr19101200 and ghs rev. Asp170 is crucial for the redox properties of vanillylalcohol oxidase. Borohydride reduction of vanillin to vanillyl alcohol. Preparation of vanillyl alcohol by sodium borohydride. Vanillyl alcohol 498000 tokyo chemical industry co.
One of the next challenges in the use of biocatalysts enzyme or microbial cells is the upgrading of biological reactions of oxidoreduction. India hazel mercantile limited for information in the india, call. Sigmaaldrich 3050 spruce street saint louis mo 63103 usa telephone. Use water spray, alcohol resistant foam, dry chemical or carbon dioxide special hazards arising from the substance or mixture. Vanillin is fully biodegradable and the products of degradation are less toxic than the product itself. Show this safety data sheet to the doctor in attendance. Vanillin, a promising biobased buildingblock for monomer synthesis article pdf available in green chemistry 164. In synthetic exercises, you are expected to know the formulas and structures of the reactants and products. Vanillyl alcohol analytical standard vanillyl alcohol sigmaaldrich. The information in this msds was obtained from current and reliable sources. It is also present in cosmetics and personal care products as a fragrance ingredient, oral care agent, hair conditioning agent, and warming or cooling agent. Firefighting measures suitable extinguishing media. Thus, the two substrates of this enzyme are vanillyl alcohol and o 2, whereas its two products are vanillin and h 2 o 2 this enzyme belongs to the family of oxidoreductases, specifically those acting on the choh group of donor with oxygen as acceptor.
Vanillyl alcohol has been used in trials studying the treatment of smoking. Cinnamyl alcohol is a strong competitive inhibitor of vanillylalcohol oxidation. Vanillyl alcohol conversion was influenced by various experimental conditions such as reaction time, temperature, molar ratio of reactants, catalyst loading, nature of solvent and reaction medium. Formation and degradation of furfuryl alcohol, 5methylfurfuryl alcohol, vanillyl alcohol, and their ethyl ethers in barrelaged wines. Physical and chemical properties physical state powder solid appearance offwhite odor sweet odor threshold no information available ph 4. Oh o h och3 nabh4 h2o oh och3 oh naoh h3bo4 vanillin m. Preparation of vanillyl alcohol by sodium borohydride reduction introduction the reduction of the carbonyl group is a versatile method for producing a multitude of other functional groups. Living cells ofsaccharomyces cerevisiae are able to bioconvert vanillin to vanillyl. It catalyzes the dehydrogenation of different 4hydroxybenzylic structures, including the conversion of 4hydroxybenzyl alcohols such. In this experiment, sodium borohydride will be used to perform the reduction.
The enzyme is a homodimeric flavoenzyme consisting of two 58 kda subunits. Buy 4hydroxy3methoxybenzyl alcohol cas 498000, a biochemical for. Bioconversion of vanillin to vanillyl alcohol in a two. After isolating the product, you will determine its melting point, determine the isolated yield of the reaction and discuss how nmr may be used to verify the reaction. Determination of gastrodin, phydroxybenzyl alcohol. Purification and characterization of vanillylalcohol. Vanillyl butyl ether is an ether of monohydroxybenzoic acid.
Indofine chemical company supplies vanillyl alcohol for pharmaceutical, agricultural and life science industries. Since the conditions for use, handling, storage and disposal of. A highperformance liquid chromatographic method for the separation and determination of gastrodin,phydroxybenzyl alcohol, vanillyl alcohol,phydroxylbenzaldehyde and vanillin in extract of chinese herbal medicine tall gastrodia tuber chinese name. Wear selfcontained breathing apparatus for firefighting if necessary. Learn vocabulary, terms, and more with flashcards, games, and other study tools. Inhibition of oxidation of human lowdensity lipoproteins by phenolic substances in different essential oils varieties. Experiment 7 preparation of vanillyl alcohol by sodium. Search results for vanillyl alcohol at sigmaaldrich. Have eyes examined and tested by medical personnel.