Sonochemical oxidation of vanillyl alcohol to vanillin in the presence of a cobalt oxide catalyst under mild conditions
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Cobalt oxide
Abstract A gas-liquid chromatographic method for vanillin and ethyl vanillin in foods has been devised. Vanillin and ethyl vanillin are extracted into methylene chloride, and the extract is purified, concentrated, and then chromatographed on an EGSS-X column. Recovery of vanillin and ethyl vanillin averaged 99.54 and 98.05%, respectively.
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This chapter contains sections titled: Introduction Biosynthesis of vanillin Production of vanillin by biotechnology Use of physical and mild chemistry Synthetic vanillin Vanillin from vanilla beans Regulations Conclusions and future outlook References
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Abstract To better control the quality of synthetic vanillin obtained by using the guaiacol synthesis method, the olfactory impacts of byproducts on the aroma of the synthetic vanillin samples were evaluated and their optimum concentration ranges were determined. Four byproducts (guaiacol, ortho‐vanillin, 5‐methyl‐vanillin, and 5‐formyl‐vanillin) were identified by gas chromatography–mass spectrometry (GC–MS) and quantified by gas chromatography–flame ionization detection (GC–FID) in the synthetic vanillin samples with different degrees of purity. The aroma intensities (AIs) of the four byproducts obtained by gas chromatography–olfactometry (GC–O) were: guaiacol (AI: 3.5–4.0, smoke), ortho‐vanillin (AI: 1.6–2.5, almond), 5‐methyl‐vanillin (AI: 2.5–3.3, aldehyde), and 5‐formyl‐vanillin (AI: 3.2–3.8, green). The aroma perceptual interactions of the four byproducts and the vanillin in the synthetic vanillin samples were determined by S‐curve analysis. Guaiacol and 5‐methyl‐vanillin showed synergistic effects by Feller's additive model. Combined with the results of an addition experiment, when the contents of guaiacol, ortho‐vanillin, 5‐methyl‐vanillin, and 5‐formyl‐vanillin were within 50, 10, 400, and 1,000 mg/kg respectively, the byproducts had no effects on the aroma quality of the synthetic vanillin samples. Practical Application Synthetic vanillin is one of the most commonly used food additives. Currently, the purity of synthetic vanillin can reach 99.9%, but trace byproducts are still present. Continuing to improve the purity of synthetic vanillin will significantly increase its production costs. Therefore, it is necessary to determine whether the presence of these byproducts affects the aroma quality of the synthetic vanillin samples or not. If they have a negative effect on its aroma, it will be important to reduce their content. If they have no influence or positive role, there is no need to control the content of these byproducts to very low levels. This study determined the content of the byproducts produced during the synthesis of vanillin by guaiacol glyoxylic acid method, judged the perceptual interaction between the byproducts and the vanillin in the synthetic vanillin samples, and determined the optimum range within which the byproducts had no effects on the aroma quality. This study provides a theoretical basis for improving the aroma quality of synthetic vanillin while controlling the production costs.
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Natural vanillin is of high interest to the flavor and fragrance industry. The present work describes that microbial strain Streptomyces L1936 isolated from microorganisms,capable of growing on ferulic acid or vanillin as the sole carbon source.Strain L1936 can produce high amounts of vanillin when grown in the presence of ferulic acid. Ferulic acid was found to be an excellent precursor for the conversion to vanillin,as doses of several 4.38g/L could be fed .This strain could transform 6g/L ferulic acid to produce 2.02g/L vanillin with a molar yield of 42.97%. A completely different metabolic flux was observed with Streptomyces L1936.During the metabolism of ferulic acid ,this strain accumulated vanillin acid only to a level of around 200mg/L and then started to accumulated vanillin as the principal metabolic product.After ferulic acid was sequentially added into the medium for two times, the concentration of vanillin reached 4.38g/L with a molar yield of 44.58%.
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Abstract Previous methods for estimating vanillin and ethyl vanillin in mixtures were long and complicated. However, this paper presents a simple chromatographic separation and quantitative determination of these aromatics, using Mitchell equipment for paper chromatography and 8 × 8” papers. Development for 2 hours separates the compounds adequately; they are then extracted and measured by absorbances at 348 mμ in alkaline solution. Recoveries of added vanillin and ethyl vanillin to vanilla extract are excellent. Aside from normal manipulative errors, the only significant inaccuracy is caused by the small amount of natural p-hy-droxybenzaldehyde in vanilla (usually equivalent to about 5% of the vanillin content). The method does not separate p-hydroxybenzaldehyde and vanillin. Total errors in the method do not exceed 0.01%. Comparison of the method with the two AOAC methods for vanillin shows that the paper chromatographic method gives results close to those by the ultraviolet absorption method, in most cases, and significantly lower results than the photometric method, which is known to give erroneously high results.
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A high performance liquid chromatographic method was developed for the simultaneous separation and determination of vanillin and o-vanillin.Influences of mobile phase composition and column temperature on the separation were investigated.Under the condition of 5% acetic acid-acetonitrile(60∶40,by volume) as mobile phase at a flow rate of 1.0 mL/min and 25 ℃,the vanillin and o-vanillin were separated in less than 5 min.The calibration curves of vanillin and o-vanillin showed good linearities in the range of 10-240 mg/L with both correlation coefficients of 0.999 7.The limits of detection(S/N=3) for vanillin and o-vanillin were 0.06 mg/L and 0.02 mg/L,respectively.The average recoveries at three spiked levels were in the range of 99%-102% with relative standard deviations of 0.2%-0.6%.The method was successfully used for the determination of vanillin and o-vanillin in real samples with satisfactory results.
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A comparison of the results of analyses of alcoholic beverage samples for vanillin by the AOAC spectrophotometric method and a GLC method are presented for 25 samples. Overall, the results were in good agreement. The GLC method distinguishes between vanillin and ethyl vanillin and eliminates interferences associated with the spectrophotometric method. The average of 12 determinations indicated a 97% recovery for added ethyl vanillin and 90% recovery for added vanillin. A mass spectrometer confirmation of ethyl vanillin and vanillin separated by the GLC was carried out.
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An ultra performance liquid chromatography(UPLC) method was developed for the simultaneous determination of vanillin, methyl vanillin and ethyl vanillin in milk powder. Samples were dissolved with water, purified with solid phase extraction column, separated with C18 column, and determined with ultra performance liquid chromatography. The results showed that there were good linear relationships between peak areas and concentrations of vanillin, methyl vanillin and ethyl vanillin in the range of 0.5~20 mg/L, with limits of detection of0.20 mg/L、0.25mg/L and 0.25 mg/L, respectively. The mean recoveries at spiked levels of 2.5~10.0 mg/L were in the range of 79.2%~102.7%, with the relative standard deviations(RSDs, n=6) of 1.85%- 4.11%. This method is sensitive and reliable, and could meet the requirements for simultaneous of vanillin, methyl vanillin and ethyl vanillin in milk powder.
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