Piperonyl alcohol
(Synonyms: 胡椒醇) 目录号 : GC63600
Piperonyl alcohol 是一种苯并二恶英衍生物。它具有生物相容性，可作为引发剂用于化学合成。
Cas No.:495-76-1
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
Piperonyl alcohol is a benzodioxole derivative. It is biocompatible and can be used in chemical synthesis as an initiator[1].
[1]. Lima GDS, et al. Long-term bonding efficacy of adhesives containing benzodioxioles as alternative co-initiators. Braz Oral Res. 2018;32:e104. Published 2018 Oct 11.
| Cas No. | 495-76-1 | SDF | |
| 别名 | 胡椒醇 | ||
| 分子式 | C8H8O3 | 分子量 | 152.15 |
| 溶解度 | DMSO : 100 mg/mL (657.25 mM; Need ultrasonic) | 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 | 6.5725 mL | 32.8623 mL | 65.7246 mL |
| 5 mM | 1.3145 mL | 6.5725 mL | 13.1449 mL |
| 10 mM | 0.6572 mL | 3.2862 mL | 6.5725 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。
Thermodynamic study of sesamol, Piperonyl alcohol, piperonylic acid and homopiperonylic acid: a combined experimental and theoretical investigation
Org Biomol Chem 2004 Mar 21;2(6):908-14.PMID:15007421DOI:10.1039/b400107a.
The standard (p(o)= 0.1 MPa) molar energies of combustion in oxygen, at T= 298.15 K, of four 1,3-benzodioxole derivatives (sesamol, Piperonyl alcohol, piperonylic acid and homopiperonylic acid) were measured by static bomb calorimetry. The values of the standard molar enthalpies of sublimation, at T= 298.15 K, were derived from vapour pressure-temperature measurements using the Knudsen effusion technique. Combining these results the standard molar enthalpies of formation of the compounds, in the gas phase, at T= 298.15 K, have been calculated: sesamol (-325.7 +/- 1.9) kJ mol(-1); Piperonyl alcohol (-329.0 +/- 2.0) kJ mol(-1); piperonylic acid (-528.9 +/- 2.6) kJ mol(-1) and homopiperonylic acid (-544.5 +/- 2.9) kJ mol(-1). The most stable geometries of all the compounds were obtained using the density functional theory with the B3LYP functional and two basis sets: 6-31G** and 6-311G**. The nonplanarity of the molecules was analyzed in terms of the anomeric effect, which is believed to arise from the interaction between a nonbonded oxygen p orbital and the empty orbital sigma*(CO) involving the other oxygen atom. Calculations were performed to obtain estimates of the enthalpies of formation of all the benzodioxoles using appropriate isodesmic reactions. There is a perfect agreement between theoretical and experimental results.
High-level expression of aryl-alcohol oxidase 2 from Pleurotus eryngii in Pichia pastoris for production of fragrances and bioactive precursors
Appl Microbiol Biotechnol 2020 Nov;104(21):9205-9218.PMID:32949280DOI:10.1007/s00253-020-10878-4.
The fungal secretome comprises various oxidative enzymes participating in the degradation of lignocellulosic biomass as a central step in carbon recycling. Among the secreted enzymes, aryl-alcohol oxidases (AAOs) are of interest for biotechnological applications including production of bio-based precursors for plastics, bioactive compounds, and flavors and fragrances. Aryl-alcohol oxidase 2 (PeAAO2) from the fungus Pleurotus eryngii was heterologously expressed and secreted at one of the highest yields reported so far of 315 mg/l using the methylotrophic yeast Pichia pastoris (recently reclassified as Komagataella phaffii). The glycosylated PeAAO2 exhibited a high stability in a broad pH range between pH 3.0 and 9.0 and high thermal stability up to 55 °C. Substrate screening with 41 compounds revealed that PeAAO2 oxidized typical AAO substrates like p-anisyl alcohol, veratryl alcohol, and trans,trans-2,4-hexadienol with up to 8-fold higher activity than benzyl alcohol. Several compounds not yet reported as substrates for AAOs were oxidized by PeAAO2 as well. Among them, cumic alcohol and Piperonyl alcohol were oxidized to cuminaldehyde and piperonal with high catalytic efficiencies of 84.1 and 600.2 mM-1 s-1, respectively. While the fragrance and flavor compound piperonal also serves as starting material for agrochemical and pharmaceutical building blocks, various positive health effects have been attributed to cuminaldehyde including anticancer, antidiabetic, and neuroprotective effects. PeAAO2 is thus a promising biocatalyst for biotechnological applications. KEY POINTS: • Aryl-alcohol oxidase PeAAO2 from P. eryngii was produced in P. pastoris at 315 mg/l. • Purified enzyme exhibited stability over a broad pH and temperature range. • Oxidation products cuminaldehyde and piperonal are of biotechnological interest. Graphical abstract.
Benzodioxole derivative as coinitiator for dental resin
Acta Odontol Scand 2007 Nov;65(6):313-8.PMID:18071954DOI:10.1080/00016350701742349.
Objective: The aim of this work was to examine whether it was possible to substitute benzodioxole derivatives for amine as coinitiators for dental application. Material and methods: A mixture of urethane dimethacrylate (UDMA)/triethylene glycol dimethacrylate (TEGDMA) (70/30 wt%), camphorquinone (CQ) and coinitiators was photocured. Real time Fourier Transform Infrared Spectroscopy with a horizontal sample holder was used to monitor the extent of polymerization. Dynamic mechanical analysis was performed over a temperature range from -50 degrees C to 200(o)C, with a ramping rate of 5(o)C per minute, using extension mode. Results: Benzodioxole derivatives as coinitiator improved the rate of polymerization and final double bond conversion of the dental resin. The cured samples showed similar properties, e.g. modulus, glass transition temperature, water sorption and solubility. Conclusion: The results indicate that two benzodioxole derivatives, Piperonyl alcohol (PAL) and benzodioxole (BDO), are viable alternatives to conventional amines as coinitiator. The biocompatibility of benzodioxole derivatives makes them more promising than amine in dental resin formulations.
Alternative co-initiators for photocurable dental resins: Polymerisation, quantum yield of conversion and cytotoxicity
Dent Mater 2022 Aug;38(8):1330-1343.PMID:35738952DOI:10.1016/j.dental.2022.06.001.
Objective: Cyclic acetals such as are naturally occurring compounds capable of acting as co-initiators during free-radical polymerisation, and potentially serve to offer non-allergic and biologically less toxic alternatives to conventional (tertiary) amines. The current study aimed to evaluate the polymerisation efficiency and potential toxicity of cyclic acetals compared with conventional photoinitiator systems in photocurable dental resins. Methods: Both, 1,3 benzodioxole (BZD) and Piperonyl alcohol (PA) were used in 0.5, 1.0, 1.5, 2.0, 3.0, 4.0 and 6.0 mol% concentrations. Whereas, N-phenyl glycine (NPG) was utilised in 0.5, 1.0, 1.5, 2.0, 3.0, 4.0 mol% concentrations for photopolymerisation of an unfilled model resin system, BisGMA and TEGDMA (1:1 mass %), involving three separate camphorquinone (CQ) concentrations of 0.5 (Low), 1.0 (Intermediate) and 1.5 (High) mol%. Conventional tertiary amines; ethyl-4-dimethyamino benzoate (EDMAB) and dimethylaminoethyl methacrylate (DMAEMA) were utilised for comparison. Real-time degree of conversion (DC, %) was evaluated using Fourier transform near-infra-red spectroscopy and quantum yield of conversion of CQ was calculated using UV-Vis spectroscopy. Cytotoxicity of NPG and cyclic acetals were assessed using MTT to determine metabolic activity of human dental pulp cells (HDPCs). Results: The cyclic acetals were capable of facilitating free radical polymerisation as co-initiators at all three CQ concentrations. Furthermore, the use of NPG as a co-initiator resulted in post-irradiation DC (%) that were comparable to both EDMAB and DMAEMA for all CQ concentrations. Alternative compounds facilitated the hydrogen abstraction process, which provided high conversion of CQ molecules. Quantum yield increased from 0.009 ± 0.0001 (0.5 mol%) to 0.03 ± 0.006 (6.0 mol%), and 0.01 ± 0.0003 (0.5 mol%) to 0.04 ± 0.001 (6.0 mol%), for respective BZD and PA formulations involving 1.0 mol% CQ. The use of NPG led to relatively higher quantum yield values (Up to 0.09 ± 0.007 at 4.0 mol%), though it exhibited competitive effects in absorbing blue light, which might be attributed to the photolytic degradation of NPG and the formation of N-methylaniline. MTT assay indicated alternative co-initiators to be comparatively less cytotoxic than EDMAB and CQ. Relative metablic activity of HDPCs treated with BZD, PA, and NPG eluates were 58.3 ± 15.7, 57.5 ± 17.4 and 64.6 ± 12.2 %, when compared with untreated HDPCs group (Control), respectively. Exposure to DMAEMA-based eluate led to relative metabolic activity (60.0 ± 0.5 %) that was comparable to that of cyclic acetals. Treatment with neat model resin eluate displayed the highest relative reduction in metabolic activity (28.9 ± 22.4) (P < 0.05), suggesting bisGMA and TEGDMA monomers played significant role in the overall cytotoxicity of photocurable systems involving HDPCs. Significance: Cyclic acetals were capable of facilitating photo-induced free radical polymerisation reactions with relatively less cytotoxicity compared with their amine counterparts, which might realise reduced cytotoxicity of photocurable materials used for dentistry and biomaterial applications.
Evaluation of alternative photoinitiator systems in two-step self-etch adhesive systems
Dent Mater 2020 Feb;36(2):e29-e37.PMID:31831181DOI:10.1016/j.dental.2019.11.008.
Objective: The aim of this study was to evaluate the effect of different photoinitiator systems on the cell viability and physico-chemical properties of an experimental adhesive resin of a two-step self-etch adhesive system. Methods: Eight photoinitiators and coinitiators were evaluated, camphorquinone (CQ); ethyl-dimethylamino benzoate (EDAB); diphenyliodonium hexafluorophosphate (DPIHFP); 1,3-benzodioxole (BDO); Piperonyl alcohol (AP); 1,3-diethyl-2-thiobarbituric acid (TBA); bisphenyl phosphinic oxide (BAPO); and diphenyl phosphinic oxide (TPO). Seven experimental adhesive resins (Bis-GMA:TEGDMA - 1:1 by wt%) were formulated by varying the initiation systems: RCQ+EDAB (control), RCQ+EDAB+DPHFP, RCQ+BDO, RCQ+AP, RCQ+TBA, RBAPO and RTPO. The cell viability of the different photoinitiators in their isolated form and after being incorporated into the adhesive resins was evaluated using the MTT assay. The degree of conversion within the hybrid layer (DC in situ) was evaluated by micro-Raman spectroscopy; the polymerization kinetics, by FTIR spectroscopy. The water sorption (Wsp) and solubility (Wsl) were calculated by using percentage of gain and loss of mass. Data were analyzed using One-way ANOVA and Kruskal-Wallis tests (α=0.05). Results: When evaluated in their isolated form, the DPIHFP was considered cytotoxic in all concentrations evaluated. When incorporated into and adhesive resin, RCQ+TBA presented higher cell viability values than control and the highest values of DC in situ (p<0.05). Additionally, the use of CQ+TBA showed a higher cell viability when compared with the conventional CQ+EDAB system. Significance: The pair CQ+TBA could be potentially useful in the development of materials with improved biocompatibility.