2,5-Dihydroxybenzoic acid
(Synonyms: 2,5-二羟基苯甲酸) 目录号 : GC33519
A benzoic acid with diverse biological activities
Cas No.:490-79-9
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
Gentisic acid is a benzoic acid that has been found in Gentiana and an active metabolite of aspirin with diverse biological activities.1,2,3,4,5 It decreases radiation-induced production of thiobarbituric acid reactive substances (TBARS), hydrogen peroxide, and protein carbonyls, increases superoxide dismutase activity, and prevents hemolysis in isolated human erythrocytes when used at concentrations ranging from 5 to 100 μM.1 Gentisic acid (1-10 μM) inhibits LDL oxidation and formation of cholesterol ester hydroperoxides in isolated human plasma.2 It induces relaxation of isolated guinea pig trachea (EC50 = 20 μM), an effect that is reduced by the large-conductance calcium-activated potassium channel blocker charybdotoxin .3 Gentisic acid (10 and 100 mg/kg) reduces cardiac hypertrophy and fibrosis and pulmonary remodeling, suppresses the renin-angiotensin-aldosterone system, and inhibits cardiac dysfunction in a mouse model of transverse aortic constriction-induced cardiac hypertrophy.4 It also prevents cardiovascular collapse and lactic acidemia in a canine model of P. aeruginosa-induced septic shock.5
1.Joshi, R.P., Gangabhagirathi, R., Venu, S., et al.Antioxidant activity and free radical scavenging reactions of gentisic acid: In-vitro and pulse radiolysis studiesFree Radic. Res.46(1)11-20(2012) 2.Ashidate, K., Kawamura, M., Mimura, D., et al.Gentisic acid, an aspirin metabolite, inhibits oxidation of low-density lipoprotein and the formation of cholesterol ester hydroperoxides in human plasmaEur. J. Pharmacol.513(3)173-179(2005) 3.Cunha, J.F., Campestrini, F.D., Calixto, J.B., et al.The mechanism of gentisic acid-induced relaxation of the guinea pig isolated trachea: The role of potassium channels and vasoactive intestinal peptide receptorsBraz. J. Med. Biol. Res.34(4)381-388(2001) 4.Sun, S., Kee, H.J., Ryu, Y.L., et al.Gentisic acid prevents the transition from pressure overload-induced cardiac hypertrophy to heart failureSci. Rep.9(1)3018(2019) 5.Mink, S., Roy Chowdhury, S.K., Gotes, J., et al.Gentisic acid sodium salt, a phenolic compound, is superior to norepinephrine in reversing cardiovascular collapse, hepatic mitochondrial dysfunction and lactic acidemia in Pseudomonas aeruginosa septic shock in dogsIntensive Care Med. Exp.4(1)24(2016)
| Cas No. | 490-79-9 | SDF | |
| 别名 | 2,5-二羟基苯甲酸 | ||
| Canonical SMILES | Oc1ccc(c(c1)C(=O)O)O | ||
| 分子式 | C7H6O4 | 分子量 | 154.12 |
| 溶解度 | DMSO : ≥ 100 mg/mL (648.85 mM); H2O : 7mg/mL (46.42 mM; ultrasonic and warming and heat to 60°C) | 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 | 6.4885 mL | 32.4423 mL | 64.8845 mL |
| 5 mM | 1.2977 mL | 6.4885 mL | 12.9769 mL |
| 10 mM | 0.6488 mL | 3.2442 mL | 6.4885 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。
2,5-Dihydroxybenzoic acid solution in MALDI-MS: ageing and use for mass calibration
J Mass Spectrom 2014 Oct;49(10):970-9.PMID:25303386DOI:10.1002/jms.3395.
2,5-Dihydroxybenzoic acid (DHB) is one of the most widely used and studied matrix compounds in matrix-assisted laser desorption/ionization (MALDI) mass spectrometry. However, the influence of ageing of the DHB solution on the MALDI mass spectra has not been yet systematically studied. In this work, the possible changes occurring in the acidified acetonitrile/water solution of the MALDI matrix compound DHB during 1-year usage period have been monitored with MALDI-Fourier transform ion cyclotron resonance mass spectrometer (MALDI-FT-ICR-MS) and attenuated total reflectance Fourier transform infrared (ATR-FT-IR) spectroscopy. No significant ageing products have been detected. The ability of the aged DHB solution to act as a MALDI matrix was tested with two materials widely used in art and conservation - bone glue (a proteinaceous material) and shellac resin (a resinous material) - and good results were obtained. A number of peaks in the mass spectra measured from the DHB solution were identified, which can be used for internal calibration of the mass axis.
Does decarboxylation make 2,5-Dihydroxybenzoic acid special in matrix-assisted laser desorption/ionization?
Rapid Commun Mass Spectrom 2014 May 30;28(10):1082-8.PMID:24711271DOI:10.1002/rcm.6885.
Rationale: Among the six positional isomers of dihydroxybenzoic acid (DHB), 2,5-DHB is a more favorable matrix for use in matrix-assisted laser desorption/ionization (MALDI) than the other isomers because of its high ion-generation efficiency at 337 and 355 nm. The generation of hydroquinone or p-benzoquinone through the decarboxylation of 2,5-DHB has been suggested to play a crucial role in the ion-generation efficiency of 2,5-DHB. Methods: The mass spectra of desorbed neutrals generated from MALDI were measured using electron impact ionization (70 eV) and a quadrupole mass spectrometer and vacuum ultraviolet (118 nm) photoionization and a time-of-flight mass spectrometer. The mass spectra of desorbed ions generated from MALDI were investigated using a time-of-flight mass spectrometer. The dissociation barrier height and dissociation rate of decarboxylation were calculated by an ab initio method and RRKM theory. Results: Decarboxylation of neutral 2,5-DHB and 2,5-DHB cations was not observed. Theoretical calculations indicated that decarboxylation of neutral 2,5-DHB and 2,5-DHB cations is too slow to occur. Conclusions: The high ion-generation efficiency of the 2,5-DHB matrix at 337 and 355 nm is not related to decarboxylation.
2,5-Dihydroxybenzoic acid butylamine and other ionic liquid matrixes for enhanced MALDI-MS analysis of biomolecules
Anal Chem 2004 May 15;76(10):2938-50.PMID:15144208DOI:10.1021/ac030354j.
The performance of the new ionic liquid MALDI-MS matrix 2,5-Dihydroxybenzoic acid butylamine (DHBB) was assessed and compared to results obtained with the ionic liquid MALDI-MS matrixes alpha-cyano-4-hydroxycinnamic acid butylamine (CHCAB), 3,5-dimethoxycinnamic acid triethylamine (SinTri), and the frequently used solid MALDI matrixes 2,5-Dihydroxybenzoic acid (DHB) and alpha-cyano-4-hydroxycinnamic acid (CHCA). The vacuum-stable, liquid consistency of ionic liquid matrix sample preparations considerably enhanced MALDI-MS analysis in terms of shot-to-shot reproducibility. Consequently, relative standard deviations serving as a measure for reproducibility of intensity-values acquired from 90 different spots on one MALDI-MS preparation were approximately one-half as high when solid DHB was replaced by the ionic liquid DHBB and eight times lower after exchange of solid CHCA by ionic liquid CHCAB. Interestingly, the ionic liquid MALDI matrix DHBB conserved the broad applicability of its solid analogue DHB, reduced MALDI induced fragmentation of monosialylated glycans and gangliosides, and was the superior ionic liquid matrix for MALDI-MS analysis of oligosaccharides and polymers, such as poly(ethylene glycol). It also worked well with glycoconjugates, peptides, and proteins; however, the tendency of DHBB to form multiple alkali adduct ions with peptides and proteins made CHCAB the ionic liquid matrix of choice for peptides. SinTri was the best ionic liquid matrix for proteins of high molecular weight, such as IgG. Furthermore, it was demonstrated for the first time that solvent properties and MALDI matrix properties of ionic liquids, such as DHBB, can be combined to enable fast, direct screening of an enzymatic reaction. This was proven by the desialylation of sialylactose with sialidase from Clostridium perfringens in the presence of diluted aqueous DHBB and subsequent direct MALDI-MS analysis of the reaction mixture.
Comparative acute nephrotoxicity of salicylic acid, 2,3-dihydroxybenzoic acid, and 2,5-Dihydroxybenzoic acid in young and middle aged Fischer 344 rats
Toxicology 1991 Mar 11;66(3):297-311.PMID:2011854DOI:10.1016/0300-483x(91)90201-b.
Experimental evidence suggests that the oxidative metabolites 2,3- and 2,5-Dihydroxybenzoic acid (DIOH) may be responsible for the nephrotoxicity of salicylic acid (SAL). In the present study, enzymuria in conjunction with glucose (GLU) and protein (PRO) excretion were used as endpoints to compare the relative nephrotoxicity of SAL with 2,3- and 2,5-DIOH. In addition, the effect of age on enzymuria and GLU and PRO excretion following treatment with SAL or 2,3- and 2,5-DIOH was investigated because the elderly are at greater risk for SAL-induced nephrotoxicity. Three and 12-month male Fischer 344 rats were administered either no treatment, vehicle, SAL, 2,3-DIOH, or 2,5-DIOH at 500 mg/kg p.o. in 5 ml/kg corn oil/DMSO (5:1). Effects of these treatments on functional integrity of renal tissue was assessed from 0--72 h after dosing by measurement of urinary creatinine, GLU, and PRO, as well as excretion of proximal and distal tubular renal enzymes. Enzymes measured as indicators of proximal tubular damage were N-acetyl-beta-glucosaminidase (NAG), gamma glutamyltransferase (GGT), alanine aminotransferase (ALT), and alkaline phosphatase (AP), while urinary lactate dehydrogenase (LD) and aspartate aminotransferase (AST) were measured as indicators of distal tubular damage. In comparison to 3-month vehicle-treated rats, 2,3- and 2,5-DIOH caused a significant increase between 0-8 h in excretion of urinary GLU and activities of AST, NAG, and LD, with peak effects occurring between 4-8 h. Toxic effects of either metabolite were not evident beyond 24 h, and toxicity of 2,5-DIOH was significantly greater in comparison to 2,3-DIOH. SAL treatment resulted in similar effects on enzymuria as well as GLU and PRO excretion, but peak effects did not occur until 16-24 h, and often persisted until 72 h after dosing. Maximal enzymuria in response to SAL treatment was significantly greater in 12- vs. 3-month rats for AST, NAG, and LD. In response to 2,3-DIOH treatment, the maximal response was significantly greater in 12- vs. 3-month rats for LD and AST, and for NAG in response to 2,5-DIOH treatment. The results of this study suggest that both 2,3- and 2,5-DIOH are nephrotoxic metabolites of SAL, but implicate 2,5-DIOH as the more potent nephrotoxic metabolite. The relative lack of an age effect for 2,3- and 2,5-DIOH vs. SAL supports the hypothesis [2] that age-related differences in biotransformation of SAL, and not increased tissue sensitivity to 2,3- or 2,5-DIOH, contribute to the age-related increase in susceptibility to SAL-induced nephrotoxicity.
A uniform 2,5-Dihydroxybenzoic acid layer as a matrix for MALDI-FTICR MS-based lipidomics
Analyst 2015 Feb 21;140(4):1298-305.PMID:25568898DOI:10.1039/c4an01964d.
A very uniform 2,5-Dihydroxybenzoic acid (DHB) layer was for the first time constructed and used as a matrix for matrix-assisted laser desorption ionization Fourier transform ion cyclotron resonance mass spectrometry (MALDI-FTICR MS) for quickly exploring the changes in lipids within biological systems. Lipid extracts from biological samples were dissolved in chloroform and deposited onto the DHB layer. Benefiting from the insolubility of DHB in chloroform, the uniform matrix crystals were still maintained, and more importantly, the lipid analytes were distributed homogeneously on the layer, which significantly increased the reproducibility of analysis using MALDI-FTICR MS. Taking advantage of the benefit of high resolution of FTICR MS and the fragment ions obtained by MS/MS, lots of lipids were identified. This method was used for exploring the changes of lipids in drug-resistant tumor cells compared with paired drug-sensitive tumor cells. The principal component analysis (PCA) and partial least-squares discriminant analysis (PLS-DA) were employed for discovery of the changed lipids. This method, characterized by the simplicity and the speediness, demonstrated a new and promising approach for lipidomics study.