Vanillyl alcohol
(Synonyms: 香草醇,p-(Hydroxymethyl)guaiacol) 目录号 : GC37887
Vanillyl alcohol (4-Hydroxy-3-methoxybenzyl alcohol, Vanillin alcohol, Vanillic alcohol, 3-Methoxy-4-hydroxybenzyl alcohol), derived from vanillin, is used to flavor food.
Cas No.:498-00-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.50%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Vanillyl alcohol (4-Hydroxy-3-methoxybenzyl alcohol, Vanillin alcohol, Vanillic alcohol, 3-Methoxy-4-hydroxybenzyl alcohol), derived from vanillin, is used to flavor food.
Vanillyl alcohol (VA) attenuates the elevation of reactive oxygen species (ROS) levels, decreases in the Bax/Bcl-2 ratio and poly (ADP-ribose) polymerase proteolysis. It protects dopaminergic MN9D cells against MPP+-induced apoptosis by relieving oxidative stress and modulating the apoptotic process[2]. VA has a suppressive effect on ferric chloride-induced lipid peroxidation in rat brains in vitro[3].
vanillyl alcohol possesses anti-angiogenic, anti-inflammatory, and anti-nociceptive activities. Vanillyl alcohol contains both anticonvulsive and suppressive effects on seizures and lipid peroxidation induced by ferric chloride in rats[1].
[1] Jung HJ, et al. Arch Pharm Res. 2008, 31(10):1275-9. [2] Kim IS, et al. Molecules. 2011, 16(7):5349-61. [3] Hsieh CL, et al. Life Sci. 2000, 67(10):1185-95.
| Cas No. | 498-00-0 | SDF | |
| 别名 | 香草醇,p-(Hydroxymethyl)guaiacol | ||
| Canonical SMILES | OCC1=CC=C(O)C(OC)=C1 | ||
| 分子式 | C8H10O3 | 分子量 | 154.16 |
| 溶解度 | DMSO: 125 mg/mL (810.85 mM) | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 6.4868 mL | 32.4338 mL | 64.8677 mL |
| 5 mM | 1.2974 mL | 6.4868 mL | 12.9735 mL |
| 10 mM | 0.6487 mL | 3.2434 mL | 6.4868 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Vanillyl alcohol oxidase
Enzymes 2020;47:87-116.PMID:32951836DOI:10.1016/bs.enz.2020.05.003.
This review presents a historical outline of the research on Vanillyl alcohol oxidase (VAO) from Penicillium simplicissimum, one of the canonical members of the VAO/PCMH flavoprotein family. After describing its discovery and initial biochemical characterization, we discuss the physiological role, substrate scope, and catalytic mechanism of VAO, and review its three-dimensional structure and mechanism of covalent flavinylation. We also explain how protein engineering provided a deeper insight into the role of certain amino acid residues in determining the substrate specificity and enantioselectivity of the enzyme. Finally, we summarize recent computational studies about the migration of substrates and products through the enzyme's structure and the phylogenetic distribution of VAO and related enzymes.
Coculture engineering for efficient production of Vanillyl alcohol in Escherichia coli
aBIOTECH 2022 Sep 5;3(4):292-300.PMID:36533265DOI:10.1007/s42994-022-00079-0.
Vanillyl alcohol is a precursor of vanillin, which is one of the most widely used flavor compounds. Currently, Vanillyl alcohol biosynthesis still encounters the problem of low efficiency. In this study, coculture engineering was adopted to improve production efficiency of Vanillyl alcohol in E. coli. First, two pathways were compared for biosynthesis of the immediate precursor 3, 4-dihydroxybenzyl alcohol in monocultures, and the 3-dehydroshikimate-derived pathway showed higher efficiency than the 4-hydroxybenzoate-derived pathway. To enhance the efficiency of the last methylation step, two strategies were used, and strengthening S-adenosylmethionine (SAM) regeneration showed positive effect while strengthening SAM biosynthesis showed negative effect. Then, the optimized pathway was assembled in a single cell. However, the biosynthetic efficiency was still low, and was not significantly improved by modular optimization of pathway genes. Thus, coculturing engineering strategy was adopted. At the optimal inoculation ratio, the titer reached 328.9 mg/L. Further, gene aroE was knocked out to reduce cell growth and improve 3,4-DHBA biosynthesis of the upstream strain. As a result, the titer was improved to 559.4 mg/L in shake flasks and to 3.89 g/L in fed-batch fermentation. These are the highest reported titers of Vanillyl alcohol so far. This work provides an effective strategy for sustainable production of Vanillyl alcohol.
On the origin of Vanillyl alcohol oxidases
Fungal Genet Biol 2018 Jul;116:24-32.PMID:29626635DOI:10.1016/j.fgb.2018.04.003.
Vanillyl alcohol oxidase (VAO) is a fungal flavoenzyme that converts a wide range of para-substituted phenols. The products of these conversions, e.g. vanillin, coniferyl alcohol and chiral aryl alcohols, are of interest for several industries. VAO is the only known fungal member of the 4-phenol oxidising (4PO) subgroup of the VAO/PCMH flavoprotein family. While the enzyme has been biochemically characterised in great detail, little is known about its physiological role and distribution in fungi. We have identified and analysed novel, fungal candidate VAOs and found them to be mostly present in Pezizomycotina and Agaricomycotina. The VAOs group into three clades, of which two clades do not have any characterised member. Interestingly, bacterial relatives of VAO do not form a single outgroup, but rather split up into two separate clades. We have analysed the distribution of candidate VAOs in fungi, as well as their genomic environment. VAOs are present in low frequency in species of varying degrees of relatedness and in regions of low synteny. These findings suggest that fungal VAOs may have originated from bacterial ancestors, obtained by fungi through horizontal gene transfer. Because the overall conservation of fungal VAOs varies between 60 and 30% sequence identity, we argue for a more reliable functional prediction using critical amino acid residues. We have defined a sequence motif P-x-x-x-x-S-x-G-[RK]-N-x-G-Y-G-[GS] that specifically recognizes 4PO enzymes of the VAO/PCMH family, as well as additional motifs that can help to further narrow down putative functions. We also provide an overview of fingerprint residues that are specific to VAOs.
Specificity of maltase to maltose in three different directions of reaction: hydrolytic, Vanillyl alcohol glucoside and Vanillyl alcohol isomaltoside synthesis
Biotechnol Prog 2012 Nov-Dec;28(6):1450-6.PMID:22927369DOI:10.1002/btpr.1628.
Vanillyl alcohol glucoside is very attractive molecule due to its very powerful physiological activity. In this article, a detailed kinetic study of transglucosylation of Vanillyl alcohol was performed. It was demonstrated that this reaction is very efficient (selectivity factor is 149) and occurred by a ping-pong mechanism with inhibition by glucose acceptor. At low concentration of Vanillyl alcohol one additional transglucosylation product was detected. Its structure was determined to be α-isomaltoside of Vanillyl alcohol, indicating that Vanillyl alcohol glucoside is a product of the first transglucosylation reaction and a substrate for second, so the whole reaction mechanism was proposed. It was demonstrated that the rate of isomaltoside synthesis is two orders of magnitude smaller than glucoside synthesis, and that maltase has interestingly high K(m) value to maltose when Vanillyl alcohol glucoside is second transglucosylation substrate.
Formation and Degradation of Furfuryl Alcohol, 5-Methylfurfuryl Alcohol, Vanillyl alcohol, and Their Ethyl Ethers in Barrel-Aged Wines
J Agric Food Chem 1998 Feb 16;46(2):657-663.PMID:10554294DOI:10.1021/jf970559r.
Furfural, 5-methylfurfural, and vanillin co-occurred in 64 barrel-aged red, white, and model wines with the reduction products, furfuryl alcohol, 5-methylfurfuryl alcohol, and Vanillyl alcohol, and with the corresponding ethyl ethers of these alcohols. Hydrolytic studies in a model wine have shown that 5-methylfurfuryl ethyl ether is formed rapidly from 5-methylfurfuryl alcohol, but both decomposed quickly under the conditions. Vanillyl ethyl ether was also formed relatively rapidly, and both this ether and Vanillyl alcohol were stable in the model wine. The formation of furfuryl ethyl ether from furfuryl alcohol and the subsequent decomposition of these two compounds were comparatively slow. The relative concentration of these aromatic alcohols and ethers in the barrel-aged wines was consistent with the observed stability of the furan derivatives, but low concentrations of Vanillyl alcohol and vanillyl ethyl ether observed in all samples showed that factors other than solvolytic degradation were responsible for reducing the concentration of these compounds in wine. Furfuryl ethyl ether, which had an aroma threshold of 430 µg/L in a white wine, was found at approximate concentrations of up to 230 µg/L in the wines.