o-Vanillin
(Synonyms: 2-Vanillin) 目录号 : GC67746o-Vanillin (2-Vanillin) 是一种天然产物，可从 Vanilla planifolia， Pinus koraiensis 的果实中提取。o-Vanillin 是一种有效的抗真菌剂。o-Vanillin 通过破坏细胞壁和细胞膜的完整性来抑制菌丝的生长。o-Vanillin 抑制 Doxorubicin 和 4-氢过氧环磷酰胺诱导的 NF-κB 激活。
Cas No.:148-53-8
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
o-Vanillin (2-Vanillin) is a nature product, could be extracted from Vanilla planifolia, Pinus koraiensis fruit. o-Vanillin is a potent antifungal agent. o-Vanillin inhibits the growth of mycelia by disrupting the integrity of cell walls and cell membranes. o-Vanillin inhibits Doxorubicin - and 4-hydroperoxycyclophosphamide-induced NF-κB activation[1][2].
o-Vanillin (2-Vanillin; 0-125 μg/mL; 24-72 h) inhibits the mycelial growth of A. flavus in a dose-dependent manner[1].
o-Vanillin (0-100 μg/mL; 48 h; A. flavus) changes the morphology of mycelia and induces irregular shrinkage of the mycelia[1].
o-Vanillin (0-100 μg/mL; A. flavus) decreases the protein content of the cell wall surface and the content of β-1,3-glucan[1].
o-Vanillin (0-100 μg/mL; A. flavus) destroys cell membrane integrity. o-Vanillin releases cell constituents and decreases extracellular pH value[1].
o-Vanillin (0-100 μg/mL) could effectively inhibit the growth of A. flavus on corn kernels[1].
o-Vanillin (0-250 μM) inhibits doxorubicin-mediated induction of NF?B activity by 65% in A375/NF?B-Luc cells. o-Vanillin suppresses 4-HC-induced activity by 43%[2].
o-Vanillin (2-Vanillin; 60 mg/kg; p.o.; daily, for 5 d) inhibits tumor growth in mice bearing A375 human melanoma xenografts[2].
| Animal Model: | Male NSG mice with A375 human melanoma xenografts (12-16 weeks of age)[2] |
| Dosage: | 60 mg/kg |
| Administration: | Oral administration; daily, for 5 days |
| Result: | Delayed the growth of A375 human melanoma xenografts in immunodeficient NSG mice. |
[1]. Li Q, et, al. o-Vanillin, a promising antifungal agent, inhibits Aspergillus flavus by disrupting the integrity of cell walls and cell membranes. Appl Microbiol Biotechnol. 2021 Jun;105(12):5147-5158.
[2]. Marton A, et, al. Vanillin Analogues o-Vanillin and 2,4,6-Trihydroxybenzaldehyde Inhibit NF?B Activation and Suppress Growth of A375 Human Melanoma. Anticancer Res. 2016 Nov;36(11):5743-5750.
| Cas No. | 148-53-8 | SDF | Download SDF |
| 别名 | 2-Vanillin | ||
| 分子式 | C8H8O3 | 分子量 | 152.15 |
| 溶解度 | DMSO : 100 mg/mL (657.25 mM; Need ultrasonic) | 储存条件 | 4°C, stored under nitrogen |
| 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 | 6.5725 mL | 32.8623 mL | 65.7246 mL |
| 5 mM | 1.3145 mL | 6.5725 mL | 13.1449 mL |
| 10 mM | 0.6572 mL | 3.2862 mL | 6.5725 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。
o-Vanillin Modulates Cell Phenotype and Extracellular Vesicles of Human Mesenchymal Stem Cells and Intervertebral Disc Cells
Cells 2022 Nov 13;11(22):3589.PMID:36429018DOI:10.3390/cells11223589.
Human mesenchymal stem cell (hMSC) and extracellular vesicle (EV) therapy is a promising treatment for discogenic low back pain (LBP). Although promising, major obstacles remain to be overcome. Cellular senescence reduces self-renewal and multipotent potentials, and the senescence-associated secretory phenotype creates an inflammatory environment negatively affecting tissue homeostasis. Reducing senescence could therefore improve regenerative approaches. Ortho-Vanillin (o-Vanillin) has senolytic activity and anti-inflammatory properties and could be a valuable supplement to MSC and EV therapy. Here, we used direct co-culture experiments to evaluate proteoglycan synthesis, inflammatory mediators, and senescent cells in the presence or absence of o-Vanillin. EV release and transfer between hMSCs and intervertebral disc cells (DCs) was examined, and the effect on hMSC differentiation and DC phenotype was evaluated in the presence and absence of o-Vanillin. This study demonstrates that o-Vanillin affects cell communication, enhances hMSC differentiation and improves DC phenotype. Co-cultures of DCs and hMSCs resulted in increased proteoglycan synthesis, a decreased number of senescent cells and decreased release of the cytokines IL6 and 8. Effects that were further enhanced by o-Vanillin. o-Vanillin profoundly increased EV release and/or uptake by hMSCs and DCs. DC markers were significantly upregulated in both cell types in response to conditioned media of o-Vanillin treated donor cells. Collectively, this study demonstrates that o-Vanillin affects hMSC and DC crosstalk and suggests that combining hMSCs and senolytic compounds may improve the outcome of cell supplementation and EV therapy for LBP.
o-Vanillin Attenuates the TLR2 Mediated Tumor-Promoting Phenotype of Microglia
Int J Mol Sci 2020 Apr 22;21(8):2959.PMID:32331440DOI:10.3390/ijms21082959.
Malignant gliomas are primary brain tumors with poor prognoses. These tumors are infiltrated by brain intrinsic microglia and peripheral monocytes which promote glioma cell invasion. In our previous studies, we discovered that the activation of Toll-like receptor 2 (TLR2) on microglia/brain macrophages converts them into a protumorigenic phenotype through the induction of matrix metalloproteinases (MMP) 9 and 14. In the present study, we used in vitro and in situ microglia-glioma interaction experimental models to test the impact of a novel inhibitor of TLR 2, ortho vanillin (o-Vanillin) to block TLR2 mediated microglia protumorigenic phenotype. We demonstrate that o-Vanillin inhibits the TLR2 mediated upregulation of MMP 9, MMP 14, IL 6 and iNOS expression. Similarly, the glioma supernatant induced MMP 9 and MMP 14 expression in murine and human microglia is abrogated by o-Vanillin treatment. o-Vanillin is not toxic for microglia, astrocytes or oligodendrocytes. Glioma growth in murine brain slice cultures is significantly reduced after treatment with o-Vanillin, and this reduced glioma growth depends on the presence of microglia. In addition, we also found that o-Vanillin inhibited the glioma induced proliferation of murine primary microglia. In summary, o-Vanillin attenuates the pro-tumorigenic phenotype of microglia/brain macrophages and thus qualifies as a candidate for glioma therapy.
o-Vanillin, a promising antifungal agent, inhibits Aspergillus flavus by disrupting the integrity of cell walls and cell membranes
Appl Microbiol Biotechnol 2021 Jun;105(12):5147-5158.PMID:34086115DOI:10.1007/s00253-021-11371-2.
o-Vanillin is a natural product that has been widely applied in the food and pharmaceutical industries. In this study, we determined that o-Vanillin can strongly inhibit the growth of Aspergillus flavus mycelia. However, the inhibition mechanism of o-Vanillin is still elusive. The ultrastructural morphology of mycelia was injured, and the cell walls were destroyed. The OH functional groups on cell walls were altered, and the content of protein in mycelial cell walls was reduced by o-Vanillin. The content of β-1,3-glucan in cell walls was significantly (P < 0.05) reduced by o-Vanillin in a dose-dependent manner, while chitin was not markedly affected. Moreover, o-Vanillin led to an increase in the permeability of cell membranes. o-Vanillin also exhibited a promising antifungal effect on contaminated corn kernels. Therefore, o-Vanillin inhibited the growth of mycelia by disrupting the integrity of cell walls and cell membranes. This study not only sheds light on the antifungal mechanism of o-Vanillin but also indicates that it is a promising agent for the control of A. flavus infection. KEY POINTS: • o-Vanillin has strong inhibitory effects on A. flavus. • o-Vanillin destroyed the integrity of cell walls and cell membranes. • o-Vanillin could effectively inhibit the growth of A. flavus on corn kernels.
2-Hy-droxy-3-meth-oxy-benzaldehyde (o-Vanillin) revisited
Acta Crystallogr Sect E Struct Rep Online 2012 Aug 1;68(Pt 8):o2336-7.PMID:22904806DOI:10.1107/S1600536812029571.
The structure of ortho-vanillin, C(8)H(8)O(3), has been revisited with modern methods and at low temperature (100 K). The previous structure [Iwasaki et al. (1976 ▶). Acta Cryst. B32, 1264-1266] is confirmed, but geometric precision is improved by an order of magnitude. The C atom of the meth-oxy group lies close to the benzene ring plane, which is the most common geometry for -OMe groups lying ortho to -OH groups on an aromatic ring. The crystal structure displays one intra-molecular O-H⋯O and three weak inter-molecular C-H⋯O hydrogen bonds.
Vanillin Analogues o-Vanillin and 2,4,6-Trihydroxybenzaldehyde Inhibit NFĸB Activation and Suppress Growth of A375 Human Melanoma
Anticancer Res 2016 Nov;36(11):5743-5750.PMID:27793895DOI:10.21873/anticanres.11157.
Background/aim: Constitutive activation of nuclear factor kappa-B (NFĸB) is a hallmark of various cancer types, including melanoma. Chemotherapy may further increase tumour NFĸB activity, a phenomenon that, in turn, exacerbates drug resistance. This study aimed at preliminary screening of a panel of aromatic aldehydes, including vanillin, for cytotoxicity and suppression of tumour cell NFĸB activity. Materials and methods: The cytotoxic and NFĸB-inhibitory effects of 10 aromatic aldehydes, including vanillin, were investigated in cultured A375 human melanoma cells. Each compound was assayed alone and in combination with the model NFĸB-activating drug doxorubicin. The most promising analogues were then tested alone and in combination with 4-hydroperoxycyclophosphamide in vitro, and with cyclophosphamide in mice bearing A375 xenografts. Results: The vanillin analogues o-Vanillin and 2,4,6-trihydroxybenzaldehyde exhibited cytotoxicity against cultured A375 cells, and inhibited doxorubicin- and 4-hydroperoxycyclophosphamide-induced NFĸB activation. They also suppressed A375 cell growth in mice. Conclusion: o-Vanillin and 2,4,6-trihydroxybenzaldehyde deserve further evaluation as potential anticancer drugs.