2-Hydroxy-4-methoxybenzaldehyde
(Synonyms: 2-羟基-4-甲氧基苯甲醛) 目录号 : GC30564
A phenol with diverse biological activities
Cas No.:673-22-3
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
2-Hydroxy-4-methoxybenzaldehyde is a phenol found in the root bark essential oil of P. sepium that has diverse biological activities, including antibacterial, antifungal, fungicidal, antioxidant, anti-virulence, and metal chelating properties.1,2,3 It is active against Gram-positive (MICs = 100-200 ?g/ml) and Gram-negative bacteria (MICs = 125-200 ?g/ml), as well as the fungus C. albicans and the phytopathogenic fungus M. oryzae (MICs = 150 and 300 ?g/ml, respectively). 2-Hydroxy-4-methoxybenzaldehyde scavenges 2,2-diphenyl-1-picrylhydrazyl (DPPH) radicals in a cell-free assay (IC50 = 9.04 mg/ml) and acts as a metal chelator, inhibiting ferrozine-Fe2+ complex formation with an IC50 value of 2.31 mg/ml. It reduces the production of the virulence factor staphyloxanthin in clinical isolates of methicillin-resistant S. aureus (MRSA) when used at a concentration of 200 ?g/ml and decreases the expression of the MRSA virulence regulatory genes saeS, geh, crtM, and sigB.2 2-Hydroxy-4-methoxybenzaldehyde, when used in combination with the antibiotics amikacin , gentamicin, cefotaxime , vancomycin , or tetracycline , increases MRSA antibiotic sensitivity. It is also an intermediate in the synthesis of Schiff base-metal complexes with antiproliferative activity.3
1.Wang, J., Liu, H., Zhao, J., et al.Antimicrobial and antioxidant activites of the root bark essential oil of Periploca sepium and its main component 2-hydroxy-4-methoxybenzaldehydeMolecules15(8)5807-5817(2010) 2.Kannappan, A., Srinivasan, R., Nivetha, A., et al.Anti-virulence potential of 2-hydroxy-4-methoxybenzaldehyde against methicillin-resistant Staphylococcus aureus and its clinical isolatesAppl. Microbiol. Biotechnol.103(16)6747-6758(2019) 3.Tyagi, P., Tyagi, M., Agrawal, S., et al.Synthesis, characterization of 1,2,4-triazole Schiff base derived 3d-metal complexes: Induces cytotoxicity in HepG2, MCF-7 cell line, BSA binding fluorescence and DFT studySpectrochim. Acta. A. Mol. Biomol. Spectrosc.171246-257(2017)
| Cas No. | 673-22-3 | SDF | |
| 别名 | 2-羟基-4-甲氧基苯甲醛 | ||
| Canonical SMILES | O=CC1=CC=C(OC)C=C1O | ||
| 分子式 | C8H8O3 | 分子量 | 152.15 |
| 溶解度 | DMSO : ≥ 50 mg/mL (328.62 mM);Water : 2 mg/mL (13.14 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 | 6.5725 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。
Scientific opinion on flavouring group evaluation 414 (FGE.414): 2-hydroxy-4-methoxybenzaldehyde
The EFSA Panel on Food Additives and Flavourings (FAF) was requested to evaluate the safety of the substance 2-hydroxy-4-methoxybenzaldehyde [FL-no: 05.229] as a new flavouring substance, in accordance with Regulation (EC) No 1331/2008. 2-Hydroxy-4-methoxybenzaldehyde belongs to chemical group 23 (Commission Regulation (EC) No 1565/2000) and is structurally related to the hydroxy- and alkoxy-ring substituted benzyl derivatives evaluated in FGE.52 and in FGE.20Rev4. The Panel considered the structural/metabolic similarity sufficient to evaluate the candidate substance following a group-based approach according to the EFSA Guidance on the data required for the risk assessment of flavourings to be used in or on foods. The information provided on the manufacturing process, the composition and the stability of [FL-no: 05.229] was considered sufficient. From studies carried out with this substance, the Panel concluded that there is no concern with respect to genotoxicity. Based on QSAR evaluation of possible metabolism, and based on information from structurally related substances, various metabolic routes can be anticipated, which only result in the formation of innocuous metabolites. The exposure estimates for [FL-no: 05.229] (24 and 60 μg/person per day for children and adults, respectively) were below the Threshold of Toxicological Concern (TTC) for its structural class (I). Accordingly, toxicity studies are not required and the Panel concluded at step A3 of the Procedure that 2-hydroxy-4-methoxybenzaldehyde is not of safety concern when used as a flavouring substance at the intended uses and use levels. Cumulative exposure estimates for 2-hydroxy-4-methoxybenzaldehyde and three structurally related substances (2.4 and 6.2 mg/kg body weight (bw) per day for adults and children, respectively) are above the TTC for structural class I, but below the ADI (acceptable daily intake) of 0-10 mg/kg bw per day for vanillin, which is one of these structurally related substances. Therefore, the cumulative exposure to these four substances [FL-no: 05.015, 05.018, 05.229 and 09.749] also does not raise a safety concern.
2-Hydroxy-4-methoxybenzaldehyde from Hemidesmus indicus is antagonistic to Staphylococcus epidermidis biofilm formation
Staphylococcus epidermidis (SE) is an opportunistic nosocomial pathogen that accounts for recalcitrant device-related infections worldwide. Owing to the growing interest in plants and their secondary metabolites targeting bacterial adhesion, this study was intended to uncover the anti-biofilm potential of Hemidesmus indicus and its major constituent 2-hydroxy-4-methoxybenzaldehyde (HMB) against SE. The minimum biofilm inhibitory concentration (MBIC) of H. indicus root extract and HMB were found to be 500 and 250 ?g ml-1, respectively. The results of time-dependent biofilm inhibition and mature biofilm disruption assays confirmed that HMB targets initial cell adhesion. Furthermore, interference by HMB in the expression of adhesin genes (icaA, aap and bhp) and biofilm components was associated with an increased susceptibility of SE to oxidative stress and antibiotics. To conclude, this study reports for the first time HMB as a potential drug against SE biofilms.
Adventitious root cultures of Decalepis salicifolia for the production of 2-hydroxy-4-methoxybenzaldehyde, a vanillin isomer flavor metabolite
Decalepis salicifolia (Bedd. ex. Hook.f.) Venter is a potential natural source of the vanillin isomer, 2-hydroxy-4-methoxybenzaldehyde (2H4MB), an aromatic compound. However, the utilization of the plant is hindered especially due to its critically endangered status and the root-specific accumulation of the compound. The use of in vitro culture techniques offers a sustainable means for the production of valuable metabolites. In this study, an efficient system was established for the production of 2H4MB in the adventitious root cultures of D. salicifolia. Leaf explants of in vitro grown plants produced on an average 4.33 ± 2.07 number of roots with root initiation frequency of 95.69 ± 3.74% in woody plant medium supplemented with 0.5 mg/L α-naphthalene acetic acid (NAA) and 1.0 mg/L kinetin (Kn). The adventitious root biomass accumulation of 10.61 ± 0.89 g fresh weight (FW) was obtained in woody plant liquid media containing 0.5 mg/L NAA and 0.3 mg/L indole-3-butyric acid (IBA) in 60 days of inoculation. Field-grown plants of the same age produced 0.30 ± 0.02 g FW, which was 35-fold lower than the adventitious root culture. The total production of 2H4MB in the same growth period was 4.9-fold higher in adventitious root culture (139.54 μg) as compared to field-grown plants (28.62 μg). Furthermore, sucrose concentration of 2% was favorable for biomass accumulation, whereas 5% was favorable for 2H4MB production. On the other hand, media pH 5.0 was suitable for biomass production and pH 7.0 was best suited for accumulation of 2H4MB. The adventitious roots also showed stable production of biomass and 2H4MB over 2 years. The established adventitious root culture system is suitable for further large-scale production of 2H4MB for flavor and fragrance industrial applications. KEY POINTS: ? Biomass accumulation was higher in adventitious root cultures than in field-grown plants. ? Manipulation of sucrose concentration and media pH led to increased 2H4MB production. ? Adventitious roots showed stable biomass and 2H4MB production over 2 years.
Anti-virulence potential of 2-hydroxy-4-methoxybenzaldehyde against methicillin-resistant Staphylococcus aureus and its clinical isolates
Burgeoning antibiotic resistance among bacterial pathogens necessitates the alternative treatment options to control the multidrug-resistant bacterial infections. Plant secondary metabolites, a significant source of structurally diverse compounds, posses several biological activities. The present study was designed to investigate the anti-virulence potential of least explored phytocompound 2-hydroxy-4-methoxybenzaldehyde (HMB) against methicillin-resistant Staphylococcus aureus (MRSA) and its clinical isolates. The minimum inhibitory concentration of HMB was found to be 1024 μg/ml. HMB at sub-MIC (200 μg/ml) exhibited a profound staphyloxanthin inhibitory activity against MRSA and its clinical isolates. Besides, growth curve analysis revealed the non-bactericidal activity of HMB at its sub-MIC. Other virulences of MRSA such as lipase, nuclease, and hemolysin were also significantly inhibited upon HMB treatment. The observations made out of blood and H2O2 sensitivity assay suggested that HMB treatment sensitized the test pathogens and aided the functions of host immune responses. Transcriptomic analysis revealed that HMB targets the virulence regulatory genes such as sigB and saeS to attenuate the production of virulence arsenal in MRSA. Further, the result of in vitro cytotoxicity assay using PBMC cells portrayed the non-toxic nature of HMB. To our knowledge, for the first time, the present study reported the virulence inhibitory property of HMB against MRSA along with plausible molecular mechanisms. Additional studies incorporating in vivo analysis and omics technologies are required to explore the anti-virulence potential of HMB and its mode of action during MRSA infections.
Explication of the Potential of 2-Hydroxy-4-Methoxybenzaldehyde in Hampering Uropathogenic Proteus mirabilis Crystalline Biofilm and Virulence
Proteus mirabilis is an important etiological agent of catheter-associated urinary tract infections (CAUTIs) owing to its efficient crystalline biofilm formation and virulence enzyme production. Hence, the present study explicated the antibiofilm and antivirulence efficacies of 2-hydroxy-4-methoxybenzaldehyde (HMB) against P. mirabilis in a non-bactericidal manner. HMB showed concentration-dependent biofilm inhibition, which was also evinced in light, confocal, and scanning electron microscopic (SEM) analyses. The other virulence factors such as urease, hemolysin, siderophores, and extracellular polymeric substances production as well as swimming and swarming motility were also inhibited by HMB treatment. Further, HMB treatment effectively reduced the struvite/apatite production as well as crystalline biofilm formation by P. mirabilis. Furthermore, the results of gene expression analysis unveiled the ability of HMB to impair the expression level of virulence genes such as flhB, flhD, rsbA, speA, ureR, hpmA, and hpmB, which was found to be in correlation with the results of in vitro bioassays. Additionally, the cytotoxicity analysis divulged the innocuous characteristic of HMB against human embryonic kidney cells. Thus, the present study reports the potency of HMB to act as a promising therapeutic remedy for P. mirabilis-instigated CAUTIs.