2-Hydroxyacetophenone
(Synonyms: 2-羟基苯乙酮) 目录号 : GC61674
2-Hydroxyacetophenone是Carissaedulis的主要根挥发物。2-Hydroxyacetophenone对HIV/SARS-CoVS假病毒的感染具有抑制作用，IC50为1.8mM。
Cas No.:582-24-1
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-Hydroxyacetophenone is a principal root volatile of the Carissa edulis[1]. 2-Hydroxyacetophenone shows inhibitory effects on infection of HIV/SARS-CoV S pseudovirus with an IC50 of 1.8 mM[2].
[1]. M D Bentley, et al. 2-Hydroxyacetophenone: principal root volatile of the East African medicinal plant, Carissa edulis. J Nat Prod. Nov-Dec 1984;47(6):1056-7. [2]. Min Zhuang, et al. Procyanidins and butanol extract of Cinnamomi Cortex inhibit SARS-CoV infection. Antiviral Res. 2009 Apr;82(1):73-81.
| Cas No. | 582-24-1 | SDF | |
| 别名 | 2-羟基苯乙酮 | ||
| Canonical SMILES | OCC(C1=CC=CC=C1)=O | ||
| 分子式 | C8H8O2 | 分子量 | 136.15 |
| 溶解度 | DMSO : 12.5 mg/mL (91.81 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 | 7.3448 mL | 36.7242 mL | 73.4484 mL |
| 5 mM | 1.469 mL | 7.3448 mL | 14.6897 mL |
| 10 mM | 0.7345 mL | 3.6724 mL | 7.3448 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。
Facile synthesis of 2-Hydroxyacetophenone from racemic styrene oxide catalyzed by engineered enzymes
Biotechnol Lett 2022 Aug;44(8):985-990.PMID:35731351DOI:10.1007/s10529-022-03271-w.
We describe a system that allows for biocatalyzed in vivo synthesis of α-hydroxy ketones from racemic epoxide starting material by in vivo co-expression of native and engineered epoxide hydrolase and alcohol dehydrogenases. The constructed expression system exploits the host cell metabolism for supply and regeneration of precious nicotinamide dinucleotide coenzyme. Racemic styrene oxide added to growth medium passively enters the cells and is hydrolyzed into (1R)-phenylethane-1,2-diol, which is subsequently oxidized to the acyloin 2-Hydroxyacetophenone. Produced 2-Hydroxyacetophenone escapes the cells via passive diffusion into the growth medium. Thus, co-expression of potato epoxide hydrolase and engineered alcohol dehydrogenase variants can be employed for robust and facile production of 2-Hydroxyacetophenone from racemic styrene oxide.
[Characterization of the affinity-tags-regulated (S)-carbonyl reductase 2 towards 2-Hydroxyacetophenone reduction]
Sheng Wu Gong Cheng Xue Bao 2021 Dec 25;37(12):4277-4292.PMID:34984874DOI:10.13345/j.cjb.210088.
The influence of different affinity tags on enzyme characteristics varies. The (S)-carbonyl reductase 2 (SCR2) from Candida parapsilosis can reduce 2-Hydroxyacetophenone, which is a valuable prochiral ketones. Different affinity tags, i.e. his-tag, strep-tag and MBP-tag, were attached to the N terminus of SCR2. These tagged SCR2 enzymes, i.e. his6-SCR2, strep-SCR2 and MBP-SCR2, were heterologously expressed in Escherichia coli and purified to study their characteristics towards 2-Hydroxyacetophenone reduction. Affinity tags did affect the characteristics of the recombinant SCR2 enzymes. Specifically, affinity tags affect the stability of recombinant SCR2 enzymes: 1) At pH 6.0, the remaining enzyme activities of his6-SCR2 and strep-SCR2 were only 95.2% and 90.0% of the untagged SCR2, while that of MBP-SCR2 was 1.2 times of the untagged SCR2 after incubating for 13 h at 30 °C. 2) The half-life of MBP-SCR2 at 50 °C was 26.6%-48.8% longer than those of strep-SCR2, his6-SCR2 and untagged SCR2. 3) The kcat of MBP-SCR2 was about 1.25-1.45 times of that of small affinity-tagged and untagged SCR2 after storing at -80 °C for 60 d. Structural informatics indicated that the α-helices at the C terminus of MBP-SCR2 contributed to the stability of the N terminus of fusion protein of SCR2. Data from circular dichroism showed that the MBP-tag has some influence on the secondary structure of SCR2, while melting temperature analysis demonstrated that the Tm of the recombinant MBP-SCR2 was about 5 °C higher than that of the untagged SCR2. This study obtained an efficient and stable recombinant SCR2, i.e. the MBP-SCR2. Moreover, this study could serve as a reference for other researchers to evaluate and select appropriate affinity tags for their research.
Photolysis, tautomerism and conformational analysis of dehydroacetic acid and a comparison with 2-Hydroxyacetophenone and 2-acetyl-1,3-cyclohexanodione
Heliyon 2020 Jul 22;6(7):e04457.PMID:32728640DOI:10.1016/j.heliyon.2020.e04457.
The purpose of this work was to determine the tautomerism, the conformational analysis and photoreactivity of dehydroacetic acid (DHAA, 1). For that reason, the photolysis of DHAA (1) was performed at 254 nm and compared with two structurally similar compounds: 2-Hydroxyacetophenone (HAP, 2) and 2-acetyl-1,3-cyclohexanodione (ACH, 3). We confirmed the degradation of 1 to acetic acid and we propose a mechanism on the assumption that a [2+2] cyclodimerization occurs (after UV light absorption) followed by some consecutive Norrish Type I cleavages, affording ketenes that end-up in acetic acid. The UV absorption study was conducted for all three compounds to gain insight about their electronic transitions, both experimentally and with computational simulations using TDDFT (B3LYP/6-31+G(d,p)) methods. A detailed analysis of the different tautomers and isomers that can be present in solution and the MOs involved in the electronic transitions was also achieved. The HOMO→LUMO transition was the least energetic optically active transition for 1 and 2, whereas 3 was recognized to have a HOMO-1→LUMO transition. These transitions were all of n→π∗ character.
Highly efficient bioreduction of 2-Hydroxyacetophenone to (S)- and (R)-1-phenyl-1,2-ethanediol by two substrate tolerance carbonyl reductases with cofactor regeneration
J Biotechnol 2017 Feb 10;243:1-9.PMID:28011130DOI:10.1016/j.jbiotec.2016.12.016.
Optically pure 1-phenyl-1,2-ethanediol is a very important chiral building block and intermediate in fine chemical and pharmaceutical industries. Reduction of 2-Hydroxyacetophenone provides a straightforward approach to access these important compounds. In this study, two enantiocomplementary carbonyl reductases, BDHA (2,3-butanediol dehydrogenase from Bacillus subtilis) and GoSCR (polyol dehydrogenase from Gluconobacter oxydans) were discovered for the first time to convert 2-Hydroxyacetophenone (2-HAP) to (R)-1-phenyl-1,2-ethanediol ((R)-PED) and (S)-1-phenyl-1,2-ethanediol ((S)-PED) with excellent stereochemical selectivity, respectively. The two enzymes were purified and characterized. In vitro bioreduction of 2-HAP catalyzed by BDHA and GoSCR coupled with glucose dehydrogenase (GDH) from Bacillus subtilis for cofactor regeneration were demonstrated, affording both (R)-PED and (S)-PED in>99% ee and 99% conversion. Recombinant Escherichia coli whole cells co-expressing both GDH and BDHA or GoSCR genes were used to asymmetric reduction of 2-HAP to (R)-PED or (S)-PED. Under the optimized conditions, the bioreduction of 400mM (54g/L) substrate was proceeded smoothly without the external addition of cofactor, and the product (R)-PED and (S)-PED were obtained with 99% yield, >99% ee and 18.0g/L/h volumetric productivity. These results offer a practical biocatalytic method for the preparation of both (R)-PED and (S)-PED with high volumetric productivity.
A New Schiff Base Based Fluorescent Sensor for Al(III) Based on 2-Hydroxyacetophenone and o-Phenylenediamine
J Fluoresc 2020 Jul;30(4):751-757.PMID:32410084DOI:10.1007/s10895-020-02527-w.
A simple Schiff base (L) based on 2-Hydroxyacetophenone and o-phenylenediamine was prepared which acts as an effective fluorescent sensor for Al3+ with ca. 9.0 fold enhancement in fluorescence intensity and detection limit 10-4.3 M. L can quite clearly distinguish Al3+ over other metal ions Zn2+, Hg2+, Cd2+, Pb2+, Mn2+, Mg2+, Co2+, Ni2+, Cu2+, Ca2+, K+, Li+, Na+ and Fe3+. Cyclic voltammogram and square wave voltammogram of L shows a significant change on interaction with Al3+. Spectroscopic data and DFT calculations confirm 1:1 interaction between L and Al3+ which is reversible with respect to Na2EDTA.