Glucovanillin
(Synonyms: 葡萄糖香草醛) 目录号 : GC36154
A vanillin precursor
Cas No.:494-08-6
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
Vanillin 4-O-β-D-glucoside is a vanillin precursor.1 It is the main storage form of vanillin in green vanilla beans.
1.Paradío, V.T., Flores, A., López, K.M., et al.Effect of endogenous and exogenous enzymatic treatment of green vanilla beans on extraction of vanillin and main aromatic compoundsJ. Food Sci. Technol.55(6)2059-2067(2018)
| Cas No. | 494-08-6 | SDF | |
| 别名 | 葡萄糖香草醛 | ||
| Canonical SMILES | O[C@H]1[C@H](O)[C@@H](O)[C@H](OC2=CC=C(C=O)C=C2OC)O[C@@H]1CO | ||
| 分子式 | C14H18O8 | 分子量 | 314.29 |
| 溶解度 | Soluble in DMSO | 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 | 3.1818 mL | 15.9089 mL | 31.8177 mL |
| 5 mM | 0.6364 mL | 3.1818 mL | 6.3635 mL |
| 10 mM | 0.3182 mL | 1.5909 mL | 3.1818 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。
Nature-inspired synthesis of antibacterial Glucovanillin derivatives
Fitoterapia 2023 Mar 20;167:105475.PMID:36940919DOI:10.1016/j.fitote.2023.105475.
The ongoing threat of Antimicrobial Resistance (AMR) complicated by the rise of Multidrug-Resistant (MDR) pathogens calls for increased efforts in the search for novel treatment options. While deriving inspiration from antibacterial natural compounds, this study aimed at using synthetic approaches to generate a series of Glucovanillin derivatives and explore their antibacterial potentials. Among the synthesized derivatives, optimum antibacterial activities were exhibited by those containing 2,4- and 3,5-dichlorophenylamino group coupled to a Glucovanillin moiety (compounds 6h and 8d respectively). In those compounds, the Minimum Inhibitory Concentrations (MIC) of 128-256 μg/mL were observed against reference and MDR strains of Klebsiella pneumoniae, Methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus faecium (VRE). Moreover, these findings emphasize the claims from previous reports on the essence of smaller molecular size, the presence of protonatable amino groups and halogens in potential antibacterial agents. The observed moderate and broad-spectrum activities of the stated derivatives point to their suitability as potential leads towards further efforts to improve their antibacterial activities.
Involvement of Colonizing Bacillus Isolates in Glucovanillin Hydrolysis during the Curing of Vanilla planifolia Andrews
Appl Environ Microbiol 2015 Aug;81(15):4947-54.PMID:25979899DOI:10.1128/AEM.00458-15.
Vanilla beans were analyzed using biochemical methods, which revealed that Glucovanillin disperses from the inner part to the outer part of the vanilla bean during the curing process and is simultaneously hydrolyzed by β-d-glucosidase. Enzymatic hydrolysis was found to occur on the surface of the vanilla beans. Transcripts of the β-d-glucosidase gene (bgl) of colonizing microorganisms were detected. The results directly indicate that colonizing microorganisms are involved in Glucovanillin hydrolysis. Phylogenetic analysis based on 16S rRNA gene sequences showed that the colonizing microorganisms mainly belonged to the Bacillus genus. bgl was detected in all the isolates and presented clustering similar to that of the isolate taxonomy. Furthermore, inoculation of green fluorescent protein-tagged isolates showed that the Bacillus isolates can colonize vanilla beans. Glucovanillin was metabolized as the sole source of carbon in a culture of the isolates within 24 h. These isolates presented unique Glucovanillin degradation capabilities. Vanillin was the major volatile compound in the culture. Other compounds, such as α-cubebene, β-pinene, and guaiacol, were detected in some isolate cultures. Colonizing Bacillus isolates were found to hydrolyze Glucovanillin in culture, indirectly demonstrating the involvement of colonizing Bacillus isolates in Glucovanillin hydrolysis during the vanilla curing process. Based on these results, we conclude that colonizing Bacillus isolates produce β-d-glucosidase, which mediates Glucovanillin hydrolysis and influences flavor formation.
Localization of beta-D-glucosidase activity and Glucovanillin in vanilla bean (Vanilla planifolia Andrews)
Ann Bot 2003 Sep;92(3):437-44.PMID:12871846DOI:10.1093/aob/mcg150.
The morphology, anatomy and histology of mature green vanilla beans were examined by light and transmission electron microscopy. Beans have a triangular cross-section with a central cavity containing seeds. Each angle is lined with tubular cells, or papillae, while the cavity sides consist of placental laminae. The epicarp and endocarp are formed by one or two layers of very small cells, while the mesocarp contains large, highly vacuolarized cells, the cytoplasm being restricted to a thin layer along the cell walls. The radial distributions of Glucovanillin and beta-glucosidase activity, measured on p-nitrophenyl-beta-glucopyranoside and Glucovanillin, are superimposable and show how beta-glucosidase activity increases from the epicarp towards the placental zone, whereas Glucovanillin is exclusively located in the placentae and papillae. Subcellular localization of beta-glucosidase activity was achieved by incubating sections of vanilla beans in a buffer containing 5-bromo-4-chloro-3-indolyl-beta-d-glucopyranoside as a substrate. Activity was observed in the cytoplasm (and/or the periplasm) of mesocarp and endocarp cells, with a more diffuse pattern observed in the papillae. A possible mechanism for the hydrolysis of Glucovanillin and release of the aromatic aglycon vanillin involves the decompartmentation of cytoplasmic (and/or periplasmic) beta-glucosidase and vacuolar Glucovanillin.
Enzymatic extraction and transformation of Glucovanillin to vanillin from vanilla green pods
J Agric Food Chem 2001 Nov;49(11):5207-9.PMID:11714304DOI:10.1021/jf010723h.
Glucovanillin was extracted from green pods and simultaneously transformed to vanillin by a combination of enzyme activities involving cell wall degradation and Glucovanillin hydrolysis. The reaction is best carried out with 47.5% v/v aqueous ethanol solution during 8 h at 70 degrees C, in a two-step enzymatic reaction using Viscozyme followed by Celluclast, two commercial enzymatic products containing mainly pectinase and cellulase activities, respectively. The extractive reaction proceeded with high efficiency with an amount of extracted vanillin 3.13 times higher than the one obtained with the Soxhlet method. The classical curing/extraction process results in 1.1-1.8 g of vanillin/100 g of dry pods. It is concluded that the enzymatic reaction may substitute the microbial process involved in tissue fermentation previous to vanillin extraction with the simultaneous hydrolysis of Glucovanillin.
Biosynthesis of vanillin via ferulic acid in Vanilla planifolia
J Agric Food Chem 2009 Nov 11;57(21):9956-61.PMID:19817415DOI:10.1021/jf901204m.
(14)C-Labeled phenylalanine, 4-coumaric acid, 4-hydroxybenzaldehyde, 4-hydroxybenzyl alcohol, ferulic acid, and methionine were applied to disks of green vanilla pods 3 and 6 months after pollination (immature and mature pods), and the conversion of these compounds to vanillin or Glucovanillin was investigated. In mature green vanilla pods, radioactivities of 11, 15, 29, and 24% from (14)C-labeled phenylalanine, 4-coumaric acid, ferulic acid, and methionine, respectively, were incorporated into Glucovanillin within 24 h. In the incorporation processes of methionine and phenylalanine into Glucovanillin, some of the (14)C labels were also trapped by the unlabeled ferulic acid. However, (14)C-labeled 4-hydroxybenzaldehyde and 4-hydroxybenzyl alcohol were not converted to Glucovanillin. On the other hand, in immature green vanilla pods radioactivities of the above six compounds were not incorporated into Glucovanillin. Although 4-coumaric acid, ferulic acid, 4-hydroxybenzaldehyde, and 4-hydroxybenzyl alcohol were converted to the respective glucose esters or glucosides and vanillin was converted to Glucovanillin, their conversions were believed to be from the detoxication of the aglycones. These results suggest that the biosynthetic pathway for vanillin is 4-coumaric acid --> --> ferulic acid --> --> vanillin --> Glucovanillin in mature vanilla pods.