4-Hydroxybenzoic acidCAS# 99-96-7 |
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| Cas No. | 99-96-7 | SDF | Download SDF |
| PubChem ID | 135 | Appearance | White powder |
| Formula | C7H6O3 | M.Wt | 138.1 |
| Type of Compound | Phenols | Storage | Desiccate at -20°C |
| Synonyms | 4-Carboxyphenol; 4-Hydroxybenzoic acid; p-Salicylic acid | ||
| Solubility | Soluble in acetone, diethyl ether, ethanol and methanol; slightly soluble in chloroform and water | ||
| Chemical Name | 4-hydroxybenzoic acid | ||
| SMILES | C1=CC(=CC=C1C(=O)O)O | ||
| Standard InChIKey | FJKROLUGYXJWQN-UHFFFAOYSA-N | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 4-Hydroxybenzoic acid, also known as p-hydroxybenzoic acid (PHBA), is a phenolic derivative of benzoic acid and widely used in organic synthesis. 4-Hydroxybenzoic acid derivatives has potential to as pan-HDAC inhibitors with anticancer properties. 4-Hydroxybenzoic acid positively regulates the expression of gum cluster to promote EPS production in PXO99A; it can inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. |
| Targets | HDAC | Antifection |
| In vitro | Antimicrobial activity of 4-hydroxybenzoic acid and trans 4-hydroxycinnamic acid isolated and identified from rice hull.[Pubmed: 9972252 ]Biosci Biotechnol Biochem. 1998 Nov;62(11):2273-6.
A Comprehensive Review on Biological activities of p-hydroxy benzoic acid and its derivatives.[Reference: WebLink]Int. J.Pharmaceut. Sci. Rev. Res., 2013, 22(2): 109-15.p-hydroxy benzoic acid (PHBA) is an organic chemical which can be obtained naturally as well as synthetically. The literature survey reveals its various biological properties viz. antimicrobial, antialgal, antimutagenic, antiestrogenic, hypoglycemic, anti-inflammatory, anti-platelet aggregating, nematicidal, antiviral, antioxidant etc. It is also reported to be used as preservative in many drugs, cosmetic products, pharmaceuticals, food and beverages. Some derivatives of 4-Hydroxybenzoic acid are found to possess direct action on Hbs molecules, inhibit acetic acid induced oedema and used in management of sickle cell disease. |
| Kinase Assay | The rice bacterial pathogen Xanthomonas oryzae pv. oryzae produces 3-hydroxybenzoic acid and 4-hydroxybenzoic acid via XanB2 for use in xanthomonadin, ubiquinone, and exopolysaccharide biosynthesis.[Pubmed: 23718125]Antiproliferative and proapoptotic activities of 4-hydroxybenzoic acid-based inhibitors of histone deacetylases.[Pubmed: 24080339]Cancer Lett. 2014 Feb 1;343(1):134-46.Histone acetyltransferases (HATs) and histone deacetylases (HDACs) regulate cellular processes by modifying the acetylation status of many proteins. Pathologically altered HDAC activity contributes to cancer development and thus characterization of novel acetylation modulators is important for future anti-cancer therapies.
Mol Plant Microbe Interact. 2013 Oct;26(10):1239-48.Xanthomonas oryzae pv. oryzae, the causal agent of rice bacterial blight, produces membrane-bound yellow pigments, referred to as xanthomonadins. Xanthomonadins protect the pathogen from photodamage and host-induced perioxidation damage. They are also required for epiphytic survival and successful host plant infection. |
4-Hydroxybenzoic acid Dilution Calculator
4-Hydroxybenzoic acid Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 7.2411 mL | 36.2056 mL | 72.4113 mL | 144.8226 mL | 181.0282 mL |
| 5 mM | 1.4482 mL | 7.2411 mL | 14.4823 mL | 28.9645 mL | 36.2056 mL |
| 10 mM | 0.7241 mL | 3.6206 mL | 7.2411 mL | 14.4823 mL | 18.1028 mL |
| 50 mM | 0.1448 mL | 0.7241 mL | 1.4482 mL | 2.8965 mL | 3.6206 mL |
| 100 mM | 0.0724 mL | 0.3621 mL | 0.7241 mL | 1.4482 mL | 1.8103 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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The rice bacterial pathogen Xanthomonas oryzae pv. oryzae produces 3-hydroxybenzoic acid and 4-hydroxybenzoic acid via XanB2 for use in xanthomonadin, ubiquinone, and exopolysaccharide biosynthesis.[Pubmed:23718125]
Mol Plant Microbe Interact. 2013 Oct;26(10):1239-48.
Xanthomonas oryzae pv. oryzae, the causal agent of rice bacterial blight, produces membrane-bound yellow pigments, referred to as xanthomonadins. Xanthomonadins protect the pathogen from photodamage and host-induced perioxidation damage. They are also required for epiphytic survival and successful host plant infection. Here, we show that XanB2 encoded by PXO_3739 plays a key role in xanthomonadin and coenzyme Q8 biosynthesis in X. oryzae pv. oryzae PXO99A. A xanB2 deletion mutant exhibits a pleiotropic phenotype, including xanthomonadin deficiency, producing less exopolysaccharide (EPS), lower viability and H2O2 resistance, and lower virulence. We further demonstrate that X. oryzae pv. oryzae produces 3-hydroxybenzoic acid (3-HBA) and 4-Hydroxybenzoic acid (4-HBA) via XanB2. 3-HBA is associated with xanthomonadin biosynthesis while 4-HBA is mainly used as a precursor for coenzyme Q (CoQ)8 biosynthesis. XanB2 is the alternative source of 4-HBA for CoQ8 biosynthesis in PXO99A. These findings suggest that the roles of XanB2 in PXO99A are generally consistent with those in X. campestris pv. campestris. The present study also demonstrated that X. oryzae pv. oryzae PXO99A has evolved several specific features in 3-HBA and 4-HBA signaling. First, our results showed that PXO99A produces less 3-HBA and 4-HBA than X. campestris pv. campestris and this is partially due to a degenerated 4-HBA efflux pump. Second, PXO99A has evolved unique xanthomonadin induction patterns via 3-HBA and 4-HBA. Third, our results showed that 3-HBA or 4-HBA positively regulates the expression of gum cluster to promote EPS production in PXO99A. Taken together, the results of this study indicate that XanB2 is a key metabolic enzyme linking xanthomonadin, CoQ, and EPS biosynthesis, which are collectively essential for X. oryzae pv. oryzae pathogenesis.
Antimicrobial activity of 4-hydroxybenzoic acid and trans 4-hydroxycinnamic acid isolated and identified from rice hull.[Pubmed:9972252]
Biosci Biotechnol Biochem. 1998 Nov;62(11):2273-6.
Two antimicrobial substances in rice hull were isolated and identified as 4-Hydroxybenzoic acid and trans 4-hydroxycinnamic acid by LC-MS, and 1H- and 13C-NMR. An evaluation of 50% inhibition of growth (IC50) revealed that the two substances had different inhibition profiles against various microorganisms. Most of the gram-positive and some gram-negative bacteria were sensitive to trans 4-hydroxycinnamic acid and 4-Hydroxybenzoic acid at IC50 concentrations of 100-170 and 160 micrograms/ml, respectively.
Antiproliferative and proapoptotic activities of 4-hydroxybenzoic acid-based inhibitors of histone deacetylases.[Pubmed:24080339]
Cancer Lett. 2014 Feb 1;343(1):134-46.
Histone acetyltransferases (HATs) and histone deacetylases (HDACs) regulate cellular processes by modifying the acetylation status of many proteins. Pathologically altered HDAC activity contributes to cancer development and thus characterization of novel acetylation modulators is important for future anti-cancer therapies. In this study, we identified three novel 4-Hydroxybenzoic acid derivatives as pan-HDAC inhibitors that increased protein acetylation levels, arrested cell cycle progression and triggered apoptotic cell death, without affecting viability of normal cells. Our data support the potential of 4-Hydroxybenzoic acid derivatives as pan-HDAC inhibitors with anticancer properties.
