1-Hydroxy-2-naphthoic acid
(Synonyms: 1-羟基-2-萘甲酸) 目录号 : GC38271
1-Hydroxy-2-naphthoic acid is a xenobiotic metabolite produced by the biodegradation of phenanthrene by microorganisms.
Cas No.:86-48-6
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
1-Hydroxy-2-naphthoic acid is a xenobiotic metabolite produced by the biodegradation of phenanthrene by microorganisms.
| Cas No. | 86-48-6 | SDF | |
| 别名 | 1-羟基-2-萘甲酸 | ||
| Canonical SMILES | O=C(O)C1=CC=C2C=CC=CC2=C1O | ||
| 分子式 | C11H8O3 | 分子量 | 188.18 |
| 溶解度 | Soluble in DMSO | 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 | 5.3141 mL | 26.5703 mL | 53.1406 mL |
| 5 mM | 1.0628 mL | 5.3141 mL | 10.6281 mL |
| 10 mM | 0.5314 mL | 2.657 mL | 5.3141 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。
Non-bioavailability of extracellular 1-Hydroxy-2-naphthoic acid restricts the mineralization of phenanthrene by Rhodococcus sp. WB9
Sci Total Environ 2020 Feb 20;704:135331.PMID:31831232DOI:10.1016/j.scitotenv.2019.135331.
Rhodococcus sp. WB9, a strain isolated from polycyclic aromatic hydrocarbons contaminated soil, degraded phenanthrene (PHE, 100 mg L-1) completely within 4 days. 18 metabolites were identified during PHE degradation, including 5 different hydroxyphenanthrene compounds resulted from multiple routes of initial monooxygenase attack. Initial dioxygenation dominantly occurred on 3,4-C positions, followed by meta-cleavage to form 1-Hydroxy-2-naphthoic acid (1H2N). More than 95.2% of 1H2N was transported to and kept in extracellular solution without further degradation. However, intracellular 1H2N was converted to 1,2-naphthalenediol that was branched to produce salicylate and phthalate. Furthermore, 131 genes in strain WB9 genome were related to aromatic hydrocarbons catabolism, including the gene coding for salicylate 1-monooxygenase that catalyzed the oxidation of 1H2N to 1,2-naphthalenediol, and complete gene sets for the transformation of salicylate and phthalate toward tricarboxylic acid (TCA) cycle. Metabolic and genomic analyses reveal that strain WB9 has the ability to metabolize intracellular 1H2N to TCA cycle intermediates, but the extracellular 1H2N can't enter the cells, restricting 1H2N bioavailability and PHE mineralization.
Prototropic forms of hydroxy derivatives of naphthoic acid within deep eutectic solvents
Phys Chem Chem Phys 2021 Apr 22;23(15):9096-9108.PMID:33885096DOI:10.1039/d1cp00845e.
Deep eutectic solvents (DESs) are not only recognized as benign and inexpensive alternatives to ionic liquids, they offer a unique solvation milieu due to the varying H-bonding capabilities of their constituents. Proton-transfer involving a probe and its prototropic forms strongly depend on the H-bonding nature of the solubilizing media. The presence of prototropic forms of three probes, 1-Hydroxy-2-naphthoic acid (1,2-HNA), 3-hydroxy-2-naphthoic acid (3,2-HNA), and 6-hydroxy-2-naphthoic acid (6,2-HNA) is investigated in two DESs, named ChCl:urea and ChCl:glycerol, constituted of H-bond acceptor choline chloride and different H-bond donors, urea and glycerol, respectively, in a 1 : 2 mole ratio under ambient conditions. While 1,2-HNA and 3,2-HNA exhibit an intramolecular H-bonding ability, 6,2-HNA does not. In contrast to common polar solvents, where the monoanionic emitting form of 1,2-HNA is also supported along with the neutral one, in both the DESs only the neutral emitting form exists. Addition of acid to the two DESs, respectively, fail to generate the monocationic form of the probe. Addition of a base to ChCl:urea results in the generation of the monoanionic form; even a very high strength of the base fails to generate the monoanionic emitting form in ChCl:glycerol. Relatively higher H-bond donating acidity of ChCl:glycerol results in added hydroxyl getting involved in H-bonding with alcohol functionalities of ChCl:glycerol leading to the absence of proton extraction to create the monoanionic form of the probe. Only the monoanionic emitting form of 3,2-HNA is present in ChCl:urea; in ChCl:glycerol, due to its higher H-bond donor acidity, the neutral emitting form is also detected. Addition of high strength of acid to ChCl:urea does result in formation of the neutral emitting form. Addition of an aqueous base results in the formation of the dianionic form of 3,2-HNA in ChCl:urea; however, in ChCl:glycerol, the added base fails to convert the neutral form of this probe to the monoanionic form as efficiently as that in ChCl:urea. The monoanionic (carboxylate) form of 6,2-HNA exits in ChCl:urea, whereas the neutral form is present in ChCl:glycerol due to its higher H-bond donating acidity. Addition of an acid can induce a shift in prototropic equilibrium towards the neutral form of 6,2-HNA in ChCl:urea; no change is observed in the behavior of this probe in ChCl:glycerol as the acid is added. Both the DESs support the dianionic form of 6,2-HNA in the presence of the base; the added base helps extract both -OH and -COOH protons of this probe. The H-bond donor component of the DES is clearly established to play a critical role in the prototropic behavior of the probe.
Biodegradation of phenanthrene by Pseudomonas sp. strain PPD: purification and characterization of 1-Hydroxy-2-naphthoic acid dioxygenase
Microbiology (Reading) 2009 Sep;155(Pt 9):3083-3091.PMID:19574301DOI:10.1099/mic.0.030460-0.
Pseudomonas sp. strain PPD can metabolize phenanthrene as the sole source of carbon and energy via the 'phthalic acid' route. The key enzyme, 1-Hydroxy-2-naphthoic acid dioxygenase (1-HNDO, EC 1.13.11.38), was purified to homogeneity using a 3-hydroxy-2-naphthoic acid (3-H2NA)-affinity matrix. The enzyme was a homotetramer with a native molecular mass of 160 kDa and subunit molecular mass of approximately 39 kDa. It required Fe(II) as the cofactor and was specific for 1-Hydroxy-2-naphthoic acid (1-H2NA), with K(m) 13.5 microM and V(max) 114 micromol min(-1) mg(-1). 1-HNDO failed to show activity with gentisic acid, salicylic acid and other hydroxynaphthoic acids tested. Interestingly, the enzyme showed substrate inhibition with a K(i) of 116 microM. 1-HNDO was found to be competitively inhibited by 3-H2NA with a K(i) of 24 microM. Based on the pH-dependent spectral changes, the enzyme reaction product was identified as 2-carboxybenzalpyruvic acid. Under anaerobic conditions, the enzyme failed to convert 1-H2NA to 2-carboxybenzalpyruvic acid. Stoichiometric studies showed the incorporation of 1 mol O(2) into the substrate to yield 1 mol product. These results suggest that 1-HNDO from Pseudomonas sp. strain PPD is an extradiol-type ring-cleaving dioxygenase.
Biodegradation of phenanthrene by Alcaligenes sp. strain PPH: partial purification and characterization of 1-Hydroxy-2-naphthoic acid hydroxylase
FEMS Microbiol Lett 2010 Oct;311(1):93-101.PMID:20727010DOI:10.1111/j.1574-6968.2010.02079.x.
Alcaligenes sp. strain PPH degrades phenanthrene via 1-Hydroxy-2-naphthoic acid (1-H2NA), 1,2-dihydroxynaphthalene (1,2-DHN), salicylic acid and catechol. Enzyme activity versus growth profile and heat stability studies suggested the presence of two distinct hydroxylases, namely 1-Hydroxy-2-naphthoic acid hydroxylase and salicylate hydroxylase. 1-Hydroxy-2-naphthoic acid hydroxylase was partially purified (yield 48%, fold 81) and found to be a homodimer with a subunit molecular weight of ∼34 kDa. The enzyme was yellow in color, showed UV-visible absorption maxima at 274, 375 and 445 nm, and fluorescence emission maxima at 527 nm suggested it to be a flavoprotein. The apoenzyme prepared by the acid-ammonium sulfate (2 M) dialysis method was colorless, inactive and lost the characteristic flavin absorption spectra but regained ∼90% activity when reconstituted with FAD. Extraction of the prosthetic group and its analysis by HPLC suggests that the holoenzyme contained FAD. The enzyme was specific for 1-H2NA and failed to show activity with any other hydroxynaphthoic acid analogs or salicylic acid. The K(m) for 1-H2NA in the presence of either NADPH or NADH remained unaltered (72 and 75 μM, respectively), suggesting dual specificity for the coenzyme. The K(m) for FAD was determined to be 4.7 μM. The enzyme catalyzed the conversion of 1-H2NA to 1,2-DHN only under aerobic conditions. These results suggested that 1-Hydroxy-2-naphthoic acid hydroxylase is a flavoprotein monooxygenase specific for 1-H2NA and different from salicylate-1-hydroxylase.
Phenanthrene degradation in Arthrobacter sp. P1-1: initial 1,2-, 3,4- and 9,10-dioxygenation, and meta- and ortho-cleavages of naphthalene-1,2-diol after its formation from naphthalene-1,2-dicarboxylic acid and hydroxyl naphthoic acids
Chemosphere 2006 Dec;65(11):2388-94.PMID:16777186DOI:10.1016/j.chemosphere.2006.04.067.
Arthrobacter sp. P1-1, isolated from a polycyclic aromatic hydrocarbon (PAH)-contaminated site in Hilo, HI, USA, can decompose phenanthrene (40 mg l(-1)) completely within 7 days. A detailed phenanthrene metabolism map was constructed based on metabolite analysis and replacement cultures. Initial dioxygenation occurs on 1,2-, 3,4-, and 9,10-C of phenanthrene, dominantly on 3,4-C positions. Rapid accumulation of 5,6- and 7,8-benzocoumarin suggests that phenanthrene-1,2- and -3,4-diols mainly undergo meta-cleavage. However, a trace amount of o-carboxyvinylnaphthoates and diphenic acid indicates a limited extent of ortho-cleavage of the diols. Naphthalene-1,2-diol, as a common and converged metabolite, was formed from 1-[(E)-2-carboxyvinyl]-2-naphthoic acid, naphthalene-1,2-dicarboxylic acid, and 1-Hydroxy-2-naphthoic acid in separate culture tests. Naphthalene-1,2-diol is then degraded in a dominant phthalic acid pathway and a minor salicylic acid pathway. Several metabolites of phthalic acid were found, while no salicylic acid metabolites were detected. The strain P1-1 likely has a very diverse set of PAH-degrading enzymes or the enzymes having relaxed substrate-specificity.