Isophorone
(Synonyms: 异佛尔酮) 目录号 : GC60951
Isophorone (IPHO), an α,β-unsaturated cyclic ketone, is a clear liquid with a camphor-like odor. Isophorone is used as a precursor to polymers.
Cas No.:78-59-1
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
Isophorone (IPHO), an α,β-unsaturated cyclic ketone, is a clear liquid with a camphor-like odor. Isophorone is used as a precursor to polymers.
[1] Shaghayegh Dezvarei, et al. Enzyme Microb Technol. 2018 Apr;111:29-37.
| Cas No. | 78-59-1 | SDF | |
| 别名 | 异佛尔酮 | ||
| Canonical SMILES | O=C1C=C(C)CC(C)(C)C1 | ||
| 分子式 | C9H14O | 分子量 | 138.21 |
| 溶解度 | 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 | 7.2354 mL | 36.1768 mL | 72.3537 mL |
| 5 mM | 1.4471 mL | 7.2354 mL | 14.4707 mL |
| 10 mM | 0.7235 mL | 3.6177 mL | 7.2354 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。
Study on the selective hydrogenation of Isophorone
RSC Adv 2021 Jan 22;11(8):4465-4471.PMID:35424410DOI:10.1039/d0ra08107h.
3,3,5-Trimethylcyclohexanone (TMCH) is an important pharmaceutical intermediate and organic solvent, which has important industrial significance. The selective hydrogenation of Isophorone was studied over noble metal (Pd/C, Pt/C, Ir/C, Ru/C, Pd/SiO2, Pt/SiO2, Ir/SiO2, Ru/SiO2), and non-noble metal (RANEY® Ni, RANEY® Co, RANEY® Cu, RANEY® Fe, Ni/SiO2, Co/SiO2, Cu/SiO2, Fe/SiO2) catalysts and using solvent-free and solvent based synthesis. The results show that the solvent has an important effect on the selectivity of TMCH. The selective hydrogenation of Isophorone to TMCH can be influenced by the tetrahydrofuran solvent. The conversion of Isophorone is 100%, and the yield of 3,3,5-trimethylcyclohexanone is 98.1% under RANEY® Ni and THF. The method was applied to the selective hydrogenation of isopropylidene acetone, benzylidene acetone and 6-methyl-5-ene-2-heptanone. The structures of the hydrogenation product target (4-methylpentan-2-one, 4-benzylbutan-2-one and 6-methyl-heptane-2-one) were characterized using 1H-NMR and 13C-NMR. The yields of 4-methylpentan-2-one, 4-benzylbutan-2-one and 6-methyl-heptane-2-one were 97.2%, 98.5% and 98.2%, respectively. The production cost can be reduced by using RANEY® metal instead of noble metal palladium. This method has good application prospects.
Polyethylene Glycol-Isophorone Diisocyanate Polyurethane Prepolymers Tailored Using MALDI MS
Materials (Basel) 2023 Jan 14;16(2):821.PMID:36676558DOI:10.3390/ma16020821.
The reaction of diols with isocyanates, leading to mono-functional and di-functional prepolymers may be investigated using various characterization methods which show the overall conversion of isocyanate monomers. On the other hand, matrix-assisted laser desorption ionization mass spectrometry (MALDI MS) polymer characterization can be employed to identify the monomer units, the end-group functionalities, molecular weight averages, and to determine the copolymer sequence. Herein, we focus on prepolymer synthesis using Isophorone diisocyanate (IPDI), a widely used diisocyanate for prepolymers preparation, especially in waterborne polyurethane materials. Thus, the reaction between polyethylene glycol diol and IPDI was in-depth investigated by mass spectrometry to determine the influence of the reaction parameters on the prepolymer's structure. The relative content of the different functional oligomer species at given reaction times was determined in the reaction mixture. More specifically, the offline analysis revealed the influence of reaction parameters such as reaction temperature, the concentration of reactants, and the amount of dibutyltin dilaurate catalyst. The established MALDI MS analysis involved measurements of samples, first, directly collected from the reaction mixture and secondly, following derivatization with methanol. The obtained results revealed the effects of reaction parameters on the functionalization reaction with isocyanates, allowing to achieve a better reaction control.
Improvement of the selectivity of Isophorone hydrogenation by Lewis acids
R Soc Open Sci 2018 May 23;5(5):171523.PMID:29892356DOI:10.1098/rsos.171523.
The selective hydrogenation of Isophorone (3,5,5-trimethyl-2- cyclohexen-1-one) to produce 3,3,5-trimethylcyclohexanone (TMCH), an important organic solvent and pharmaceutical intermediate, is of significance in industry. However, the over-hydrogenation to produce the by-product 3,3,5-trimethylcyclohexanol causes issues. Up to now, it is still a challenge to hydrogenate Isophorone to TMCH with high selectivity. In this work, we found that Lewis acids could inhibit the hydrogenation of C=O bond on Isophorone, thus greatly improving the selectivity towards TMCH. In addition, added solvents like supercritical CO2 also had a positive impact on the selectivity. Both the conversion and selectivity could be increased to more than 99% when suitable Lewis acid and solvent were employed. Nevertheless, Lewis acid also exhibited some inhibition on the hydrogenation of the C=C bond of Isophorone. Hence, a relatively weak Lewis acid, ZnCl2, is suitable for the selective hydrogenation.
Isophorone derivatives as a new structural motif of aggregation pheromones in Curculionidae
Sci Rep 2019 Jan 28;9(1):776.PMID:30692570DOI:10.1038/s41598-018-37156-8.
The beetle Homalinotus depressus (Coleoptera: Curculionidae) is a major pest of coconuts in the Northern region of Brazil, for which environmentally friendly methods of control are desired. Behavioral responses of H. depressus to airborne volatile extracts from conspecifics suggested the presence of a male-produced aggregation pheromone. GC analyses of these extracts showed the presence of four male-specific compounds. Analytical data in combination with the synthesis of standards led to the identification of the male-released semiochemicals as epoxyisophorone (1), Isophorone (2), homalinol (3), and 2-hydroxyisophorone (4), of which (3) was the major constituent. The configuration of homalinol was determined to be cis on the basis of retention times of synthetic cis and trans synthetic standards. Enantiomers of cis-homalinol were obtained in high enantiomeric excess by using biocatalysis. Their separation on a GC enantioselective column (β-Dex325®), allowed us to unambiguously determine that the absolute configuration of natural homalinol was (1R,2R,6S). Field bioassays demonstrated that both the synthetic major compound per se and mixtures of all four male-specific compounds were attractive to H. depressus.
Two-isophorone fluorophore-based design of a ratiometric fluorescent probe and its application in the sensing of biothiols
J Mater Chem B 2019 Oct 7;7(37):5633-5639.PMID:31483434DOI:10.1039/c9tb01671f.
2,4-Dinitrobenzenesulfonyl (DNBS) has been widely used for the design of small fluorescent probes for biothiols due to its high reactivity. However, most DNBS-based fluorescent probes exhibit "off-on" fluorescence response towards biothiols due to the strong quenching effects of DBNS on the fluorophores. Herein, we present an alternative design of a ratiometric fluorescent probe based on DNBS for biothiols. A new fluorophore bearing two Isophorone malononitrile structures was conjugated with DNBS to provide a target probe (CHT), which exhibited a ratiometric sensing behavior towards biothiols. The sensing process is rapid and highly selective. Most importantly, CHT has high stability in the quantitative detection of Cys compared to the control probe CHM, which performed an "off-on" sensing for biothiols. Endogenous biothiols were successfully monitored with CHT in live cells through the ratiometric fluorescence signal. This new fluorophore bearing two Isophorone malononitrile moieties will pave a new avenue to design ratiometric fluorescent probes for imaging and quantitative detection.