2,5-Dihydroxybenzaldehyde
(Synonyms: 2,5-二羟基苯甲醛,Gentisaldehyde) 目录号 : GC60464
A building block
Cas No.:1194-98-5
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >97.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
2,5-Dihydroxybenzaldehyde is a building block.1,2 It has been used in the synthesis of 2,4-dimethylbenzoylhydrazones with antileishmanial and antioxidant activity.
1.Taha, M., Baharudin, M.S., Ismail, N.H., et al.Synthesis of 2-methoxybenzoylhydrazone and evaluation of their antileishmanial activityBioorg. Med. Chem. Lett.23(11)3463-3466(2013) 2.Taha, M., Ismail, N.H., Jamil, W., et al.Synthesis, evaluation of antioxidant activity and crystal structure of 2,4-dimethylbenzoylhydrazonesMolecules18(9)10912-10929(2013)
| Cas No. | 1194-98-5 | SDF | |
| 别名 | 2,5-二羟基苯甲醛,Gentisaldehyde | ||
| Canonical SMILES | O=CC1=CC(O)=CC=C1O | ||
| 分子式 | C7H6O3 | 分子量 | 138.12 |
| 溶解度 | DMF: 15mg/mL,DMSO: 15mg/mL,Ethanol: 5mg/mL,PBS (pH 7.2): 2mg/mL | 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 | 7.2401 mL | 36.2004 mL | 72.4008 mL |
| 5 mM | 1.448 mL | 7.2401 mL | 14.4802 mL |
| 10 mM | 0.724 mL | 3.62 mL | 7.2401 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。
Mechanisms of Antimicrobial Action of Cinnamon and Oregano Oils, Cinnamaldehyde, Carvacrol, 2,5-Dihydroxybenzaldehyde, and 2-Hydroxy-5-Methoxybenzaldehyde against Mycobacterium avium subsp. paratuberculosis (Map)
Foods 2017 Aug 24;6(9):72.PMID:28837070DOI:10.3390/foods6090072.
The antimicrobial modes of action of six naturally occurring compounds, cinnamon oil, cinnamaldehyde, oregano oil, carvacrol, 2,5-Dihydroxybenzaldehyde, and 2-hydroxy-5-methoxybenzaldehyde, previously found to inhibit the growth of Mycobacterium avium subsp. paratuberculosis (Map) reported to infect food animals and humans and to be present in milk, cheese, and meat, were investigated. The incubation of Map cultures in the presence of all six compounds caused phosphate ions to leak into the extracellular environment in a time- and concentration-dependent manner. Cinnamon oil and cinnamaldehyde decreased the intracellular adenosine triphosphate (ATP) concentration of Map cells, whereas oregano oil and carvacrol caused an initial decrease of intracellular ATP concentration that was restored gradually after incubation at 37 °C for 2 h. Neither 2,5-Dihydroxybenzaldehyde nor 2-hydroxy-5-methoxybenzaldehyde had a significant effect on intracellular ATP concentration. None of the compounds tested were found to cause leakage of ATP to the extracellular environment. Monolayer studies involving a Langmuir trough apparatus revealed that all anti-Map compounds, especially the essential oil compounds, altered the molecular packing characteristics of phospholipid molecules of model membranes, causing fluidization. The results of the physicochemical model microbial membrane studies suggest that the destruction of the pathogenic bacteria might be associated with the disruption of the bacterial cell membrane.
Sequential C-N and C-O bond formation in a single pot: synthesis of 2H-benzo[b][1,4]oxazines from 2,5-Dihydroxybenzaldehyde and amino acid precursors
Org Lett 2012 Jan 20;14(2):552-5.PMID:22216942DOI:10.1021/ol2031747.
Functionalized β-aryl alanine ester derivatives were found to undergo rapid C-N and C-O bond formation with quinol carbonyl compounds to afford 2H-benzo[b][1,4]oxazines in good to excellent yields. This unprecedented finding reported herein offers a straightforward, highly efficient, and rapid method for the synthesis of 2H-benzo[b][1,4]oxazines.
Gentisaldehyde and Its Derivative 2,3-Dihydroxybenzaldehyde Show Antimicrobial Activities Against Bovine Mastitis Staphylococcus aureus
Front Vet Sci 2018 Jul 11;5:148.PMID:30050910DOI:10.3389/fvets.2018.00148.
Bovine mastitis is a worldwide disease of dairy cattle associated with significant economic losses for the dairy industry. One of the most common pathogens responsible for mastitis is Staphylococcus (S.) aureus. Due to the development and spreading of antibiotic resistance, the search for novel antimicrobial substances against S. aureus is of great importance. The aim of this study was to evaluate two dihydroxybenzaldehydes for the prevention of bovine mastitis. Therefore we determined the minimal inhibitory concentration (MICs) of gentisaldehyde (2,5-Dihydroxybenzaldehyde) and 2,3-dihydroxybenzaldehyde of a diverse set of 172 bovine mastitis S. aureus isolates using an automated robot-based microdilution method. To characterize the bovine isolates we determined the genotype by spa-typing, the antimicrobial resistance to eight antibiotic classes using the disk diffusion method and the MICs of three commonly used antiseptics (benzalkonium chloride, chlorhexidine, and iodine). Further we investigated the cytotoxicity of gentisaldehyde and 2,3-dihydroxybenzaldehyde in bovine mammary epithelial MAC-T cells using the XTT assay. The S. aureus strains showed a high genetic diversity with 52 different spa-types, including five novel types. Antibiotic susceptibility testing revealed that 24% of isolates were resistant to one antimicrobial agent and 3% of isolates were multi-resistant. The occurrence of antibiotic resistance strongly correlated with the spa-type. Both dihydroxybenzaldehydes showed antimicrobial activities with a MIC50 of 500 mg/L. The MIC of gentisaldehyde significantly correlated with that of 2,3-dihydroxybenzaldehyde, whereas no correlation was observed with the MIC of the three antiseptics. Cytotoxicity testing using bovine mammary epithelial MAC-T cells revealed that gentisaldehyde and 2,3-dihydroxybenzaldehyde show low toxicity at MIC50 and MIC90 concentrations. In conclusion, gentisaldehyde and 2,3-dihydroxybenzaldehyde exhibited antimicrobial activities against a diverse range of bovine mastitis S. aureus strains at low-cytotoxic concentrations. Therefore, both compounds are potential candidates as antiseptics to prevent bovine mastitis and to reduce the use of antibiotics in dairy cows.
A bioanode based on MWCNT/protein-assisted co-immobilization of glucose oxidase and 2,5-Dihydroxybenzaldehyde for glucose fuel cells
Biosens Bioelectron 2010 Jul 15;25(11):2515-21.PMID:20472420DOI:10.1016/j.bios.2010.04.016.
This paper describes an easy-to-prepare, robust bioanode constructed on a polyester-supported screen-printed carbon paste electrode (SPCE) for glucose biofuel cells. To prepare the bioanode, carboxylated multi-walled carbon nanotubes (MWCNTs) were drop-coated on the SPCE first, and then a crosslinked matrix composed of glucose oxidase (GOx), 2,5-Dihydroxybenzaldehyde (DHB), bovine serum albumin (BSA) and glutaraldehyde was coated atop the MWCNTs. It was found that the MWCNTs assisted the immobilization of the crosslinked matrix, enhanced the electron-shuttling process, and showed electrocatalytic effect to gluconic acid, which allowed squeeze more electrons out of a glucose molecule. Inside the matrix, DHB mediators could couple to GOx and BSA via the Schiff base reaction, and GOx and BSA could crosslink to each other with glutaraldehyde. From cyclic voltammetry, it was estimated that 3.63 nmol cm(-2) of DHB was anchored on the bioanode, and no mediator leaching was observed. The bioanode also attained reproducible flow-injection analysis (FIA) signals for glucose sensing (RSD=4.99%) and retained 84% of the initial response after keeping in a buffer at 4 degrees C for a week. In addition, the bioanode obeyed the Michaelis-Menten kinetics. Finally, we demonstrated that a glucose biofuel cell assembled with an optimal bioanode and a laccase/ABTS cathode generated an electric power of 45 microW cm(-2) from 1M glucose at 37 degrees C.
Concise Syntheses of Violaceoids A and C
Chem Pharm Bull (Tokyo) 2021 Feb 1;69(2):232-235.PMID:33239487DOI:10.1248/cpb.c20-00816.
The concise syntheses of two alkylated hydroquinone natural products, violaceoids A and C, were accomplished by a protecting-group-free method employing the commercially available 2,5-Dihydroxybenzaldehyde as the starting material. The key strategy of the syntheses is the utilization of alkenylboronic acid as both the coupling and temporary protective reagents to efficiently introduce the requisite alkenyl side chain of violaceoid A. Moreover, the synthesis of violaceoid C is reported here for the first time.