Isophorone - 10mM in DMSO , CAS No.78-59-1

CAS: 78-59-1 Cat. No.: I425954 Molecular Weight: 138.21 Beilstein Registry Number: 1280721 EC Number: 201-126-0

GRADE & PURITY 10mM in DMSO

Synonyms

3,5,5-Trimethyl-2-cyclohexenone | .alpha.-Isophorone | 3,3,5-trimethyl-cyclohex-5-en-1-one | 1,3,3-TRIMETHYLCYLOHEXEN-5-ONE | AKOS025243269 | I0151 | InChI=1/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H | Isophoron | NCGC00164006-01 | SCHEMBL22522 | 3,5,

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

Isophorone is used as a solvent and as an intermediate in organic synthesis. Isophorone also occurs naturally in cranberries. Isophorone is used as a solvent in some printing inks, paints, lacquers, adhesives, copolymers, coatings, finishings

Specifications

Synonyms

3, 5, 5-Trimethyl-2-cyclohexenone | .alpha.-Isophorone | 3, 3, 5-trimethyl-cyclohex-5-en-1-one | 1, 3, 3-TRIMETHYLCYLOHEXEN-5-ONE | AKOS025243269 | I0151 | InChI=1/C9H14O/c1-7-4-8(10)6-9(2, 3)5-7/h4H, 5-6H2, 1-3H | Isophoron | NCGC00164006-01 | SCHEMBL22522 | 3, 5,

Specifications & Purity

10mM in DMSO

Storage

Protected from light, Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Names and Identifiers

• Canonical Smiles: CC1=CC(=O)CC(C1)(C)C
• IUPAC Name: 3,5,5-trimethylcyclohex-2-en-1-one
• InChIKey: HJOVHMDZYOCNQW-UHFFFAOYSA-N
• INCHI: 1S/C9H14O/c1-7-4-8(10)6-9(2,3)5-7/h4H,5-6H2,1-3H3
• Isomeric SMILES: CC1=CC(=O)CC(C1)(C)C
• WGK Germany: 1
• RTECS: GW7700000
• UN Number: 1993
• Packing Group: I
• Molecular Weight: 138.21
• Beilstein: 1280721
• Reaxy-Rn: 1280721
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1280721&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbonyl compounds
        • Level5 Ketones
          • Level6 Cyclic ketones
            • Level7 Cyclohexenones

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbonyl compounds
• Intermediate Tree Nodes: Ketones - Cyclic ketones
• Direct Parent: Cyclohexenones
• Alternative Parents: Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aliphatic homomonocyclic compounds
• Substituents: Cyclohexenone - Organic oxide - Hydrocarbon derivative - Aliphatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as cyclohexenones. These are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
• External Descriptors: cyclic ketone - enone

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive.
• Refractive Index: 1.476
• Flash Point(°F): 204.8 °F
• Flash Point(°C): 96 °C
• Boil Point(°C): 213-214°C
• Melt Point(°C): -8°C
• Molecular Weight: 138.210 g/mol
• XLogP3: 1.600
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 138.104 Da
• Monoisotopic Mass: 138.104 Da
• Topological Polar Surface Area: 17.100 Ų
• Heavy Atom Count: 10
• Formal Charge: 0
• Complexity: 187.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Yixuan Yao, Fudong Zeng, Liangqiang Wu, Shuo Xing, Qingbiao Yang, Yaoxian Li.  (2023)  A novel “on–off–on” near-infrared fluorescent probe for Cu2+ and S2− continuous detection based on dicyanoisoflurone derivatives, and its application in bacterial imaging.  Analytical Methods,  15  (40): (5329-5340).  [PMID:37791492] [10.1039/D3AY01339A]

2. Yong Lin, Xiaolian Chen, Qianying Lu, Jiayi Wang, Chen Ding, Fuxing Liu, Desheng Kong, Wei Yuan, Wenming Su, Zheng Cui.  (2023)  Thermally Laminated Lighting Textile for Wearable Displays with High Durability.  ACS Applied Materials & Interfaces,      [PMID:36688806] [10.1021/acsami.2c20681]

3. Yuanyuan Cui, Yaoyang Meng, Yun Hu, Yuqi Chen, Yixian Yang, Min Fang, Cun Li, Weiju Zhu.  (2022)  A novel lipid droplets-targeting fluorescent probe based on dicyanisophorone and carbazole for Cu2+ and its application.  JOURNAL OF THE CHINESE CHEMICAL SOCIETY,  70  (1): (68-75).  [PMID:] [10.1002/jccs.202200401]

4. Chao Wang, Wazhen Xu, Yuqi Yuan, Yuke Zhai, Tengfei Hu, Jianan Huang, Zhonghua Liu, Qin Li.  (2022)  Characterization and modelling of odor-active compounds release behavior from Fu-brick tea during boiling-water extraction by molecular sensory science approach.  Food Chemistry-X,      [PMID:36845510] [10.1016/j.fochx.2022.100551]

5. Yun-Jiao Ma, Tao Zhou, Wei Jiang, Bei-Wei Zhu, Ming Du, Xian-Bing Xu.  (2022)  Balanced extraction of volatile and semi-volatile compounds by dynamic linked position unity solid-phase microextraction.  FOOD CHEMISTRY,      [PMID:36508869] [10.1016/j.foodchem.2022.135160]

6. Li Liu, Yixian Yang, Yuanyuan Cui, Weiju Zhu, Min Fang, Cun Li.  (2022)  A novel dicyanisophorone-based colorimetric and ratiometric fluorescent probe for the detection of hypochlorite in the environment and living cells.  DYES AND PIGMENTS,      [PMID:] [10.1016/j.dyepig.2022.110879]

7. Chen Ding, Jiayi Wang, Wei Yuan, Xiaojin Zhou, Yong Lin, Guoqing Zhu, Jie Li, Tao Zhong, Wenming Su, Zheng Cui.  (2022)  Durability Study of Thermal Transfer Printed Textile Electrodes for Wearable Electronic Applications.  ACS Applied Materials & Interfaces,      [PMID:35723443] [10.1021/acsami.2c03807]

8. Ling Yan, Qing-Song Gu, Wen-Li Jiang, Min Tan, Zhi-Ke Tan, Guo-Jiang Mao, Fen Xu, Chun-Yan Li.  (2022)  Near-Infrared Fluorescent Probe with Large Stokes Shift for Imaging of Hydrogen Sulfide in Tumor-Bearing Mice.  ANALYTICAL CHEMISTRY,      [PMID:35360906] [10.1021/acs.analchem.1c04169]

9. Chao Wang, Juan Li, Ya Zhang, Zhongrong He, Yin Zhang, Xingmin Zhang, Zhuoyue Guo, Jianan Huang, Zhonghua Liu.  (2021)  Effects of electrostatic spray drying on the sensory qualities, aroma profile and microstructural features of instant Pu-erh tea.  FOOD CHEMISTRY,      [PMID:34799127] [10.1016/j.foodchem.2021.131546]

10. Shan-Shan Zhang, Sen Guo, Zhao-Jing Zheng, Shao-Jing Liu, Yu-Fei Hou, Chi-Tang Ho, Nai-Sheng Bai.  (2021)  Characterization of volatiles in Allium tenuissimum L. flower by headspace-gas chromatography-olfactometry-mass spectrometry, odor activity values, and the omission and recombination experiments.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2021.112144]

11. Qianqian Xu, Xueru Sheng, Na Li, Jian Zhang, Haiqiang Shi, Meihong Niu, Qingwei Ping, Ning Li.  (2021)  Ball-Milling: A Productive, Economical, and Widely Applicable Method for Condensation of Biomass-Derived Aldehydes and Ketones at Mild Temperatures.  ACS Sustainable Chemistry & Engineering,      [PMID:] [10.1021/acssuschemeng.1c02270]

12. Wei Bing, Faming Wang, Yuhuan Sun, Jinsong Ren, Xiaogang Qu.  (2021)  Catalytic asymmetric hydrogenation reaction by in situ formed ultra-fine metal nanoparticles in live thermophilic hydrogen-producing bacteria.  Nanoscale,  13  (17): (8024-8029).  [PMID:33900349] [10.1039/D1NR00327E]

13. Yang Tian, Dong-Ye Zhou, Wen-Li Jiang, Zun-Pan She, Yongfei Li, Chun-Yan Li.  (2020)  Novel near-infrared fluorescence probe with large Stokes shift for monitoring CCl4-induced toxic hepatitis.  TALANTA,      [PMID:33303166] [10.1016/j.talanta.2020.121720]

14. Junjian Xie, Xiangwen Zhang, Chengxiang Shi, Lun Pan, Fang Hou, Genkuo Nie, Jiawei Xie, Qing Liu, Ji-Jun Zou.  (2019)  Self-photosensitized [2 + 2] cycloaddition for synthesis of high-energy-density fuels.  Sustainable Energy & Fuels,  4  (2): (911-920).  [PMID:] [10.1039/C9SE00863B]

15. Junjian Xie, Lun Pan, Genkuo Nie, Jiawei Xie, Yakun Liu, Chi Ma, Xiangwen Zhang, Ji-Jun Zou.  (2019)  Photoinduced cycloaddition of biomass derivatives to obtain high-performance spiro-fuel.  GREEN CHEMISTRY,  21  (21): (5886-5895).  [PMID:] [10.1039/C9GC02790D]

16. Jiawei Xie, Lei Zhang, Xiangwen Zhang, Peijuan Han, Junjian Xie, Lun Pan, De-Rong Zou, Song-Hua Liu, Ji-Jun Zou.  (2018)  Synthesis of high-density and low-freezing-point jet fuel using lignocellulose-derived isophorone and furanic aldehydes.  Sustainable Energy & Fuels,  2  (8): (1863-1869).  [PMID:] [10.1039/C8SE00197A]

17. Yucui Hou, Shuhang Ren, Muge Niu, Weize Wu.  (2018)  Improvement of the selectivity of isophorone hydrogenation by Lewis acids.  Royal Society Open Science,  5  (5):   [PMID:29892356] [10.1098/rsos.171523]

18. Wu Zhengjun, Zhao Taotao, Jiang Xingyue, Zhang Dan, Wang Feiyi, Ren Xiaoming, Wang Zhao, Wang Erfei, Ren Jun.  (2024)  A near-infrared fluorescent probe with a large Stokes shift for the detection and imaging of biothiols in vitro and in vivo.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,      [PMID:39322801] [10.1007/s00216-024-05537-w]

19. Yunhuan Yuan, Chaogang Ding, Rui Yin, Shun Lu, Jie Xu, Wei Ren, Kang Li, Weiwei Zhao.  (2024)  A Strategy for Fabricating Ultra-Flexible Thermoelectric Films Using Ag2Se-Based Ink.  Materials,  17  (15): (3784).  [PMID:39124453] [10.3390/ma17153784]

20. Yixuan Yao, Fudong Zeng, Jinli Ma, Liangqiang Wu, Shuo Xing, Haiqin Yang, Yapeng Li, Jianshi Du, Qingbiao Yang, Yaoxian Li.  (2024)  An innovative near-infrared fluorescent probe with FRET effect for the continuous detection of Zn2+ and PPi with high sensitivity and selectivity, and its application in bioimaging.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:38184879] [10.1016/j.saa.2024.123837]

21. Jiahao Li, Yong Lin, Dong Zhou, Shuo Zhang, Wei Yuan, Wenming Su, Xiuqing Meng, Xinzhou Wu, Congcong Chi, Desheng Kong, Zheng Cui.  (2025)  High-brightness low voltage alternative current electroluminescent devices for human wearable displays.  OPTICS AND LASER TECHNOLOGY,      [PMID:] [10.1016/j.optlastec.2025.112568]

22. Zetong Meng, Jing Liu, Ting Yu, Zhuobin Shang, Yu Wang, Shaomin Shuang.  (2024)  Novel ratiometric fluorescent probe with large Stokes shift for selective sensing and imaging of Zn2+ in live cell.  SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY,      [PMID:38875927] [10.1016/j.saa.2024.124645]

23. Mingya Wang, Hongxia Pan, Yongzheng Liu, Jun Chen, Duanlin Cao, Linxiu Zhao.  (2025)  Solubility and Thermodynamic Analysis of 3(5)-Nitropyrazole in Different High Boiling Solvents.  JOURNAL OF CHEMICAL AND ENGINEERING DATA,      [PMID:] [10.1021/acs.jced.4c00446]

24. Lucheng Chen, Jiaying Yu, Qi Liu, Jiaxing Han, Daoxiang Su, Zhifei Wang.  (2025)  Synthesis of a Turn-On Isophorone-Based Near-Infrared Fluorescent Probe for Specific Recognition of Carboxylesterase 2 and Bioimaging.  ANALYTICAL LETTERS,      [PMID:] [10.1080/00032719.2025.2481627]

25. Minghan Yu, Jiayun Feng, SenPei Xie, Yiping Wang, Yongsheng Li, Runze Wang, Guofeng Lu, Kang Li, Rui Wu, Weiwei Zhao, Yanhong Tian.  (2025)  Synthesis of Thick-shell Cu@Ag Particles with Nanorod-shape Surface Morphology for Printed Electronics.  JOURNAL OF ALLOYS AND COMPOUNDS,      [PMID:] [10.1016/j.jallcom.2025.179870]

26. Zu Panru, Yu Yanchao, Li Bolin, You Jun, Wu Wenju, Wu Mianyuan.  (2025)  Visual Detection of Cadmium and Glutathione by Dicyanoisophorone Fluorescent Probe and its Portable Application.  JOURNAL OF FLUORESCENCE,      [PMID:40616651] [10.1007/s10895-025-04436-2]

27. Jiayu Xu, Tongxin Sun, Yuan Guo, Taotao Wu, Jinge Hu, Yunhao Lin, Longyuan Yang, Ying Gao, Tianruo Shen.  (2025)  Conversion of high-value products from biomass aqueous phase through enzymatic-hydrothermal treatment.  BIOMASS & BIOENERGY,      [PMID:] [10.1016/j.biombioe.2025.108348]

28. Xiang-yu Kong, Shao-Min Shuang, Yue-tao Zhang, Yu Wang, Chuan Dong.  (2022)  Dicyanoisophorone-based fluorescent probe with large Stokes shift for ratiometric detection and imaging of exogenous/endogenous hypochlorite in cell and zebrafish.  TALANTA,      [PMID:35189411] [10.1016/j.talanta.2022.123293]

29. Liu Xingyu, Li Xiangqian, Dong Pei, Wu Zhiming, Gao Jinwei, Wang Qianming.  (2020)  Near-infrared emission tracks inter-individual variability of carboxylesterase-2 via a novel molecular substrate.  MICROCHIMICA ACTA,  187  (6): (1-10).  [PMID:32377952] [10.1007/s00604-020-04296-6]

30. Meng Tao, Wenli Guo, Jin Liang, Zhengquan Liu.  (2024)  Unraveling the key cooked off-flavor compounds in thermally sterilized green tea beverages, and masking effect of tea raw material baking.  FOOD CHEMISTRY,      [PMID:39423534] [10.1016/j.foodchem.2024.141671]

31. Meiqing Zhu, Manjie Chen, Xinfu Zhu, Xingyu Zhu, Rimao Hua, Xiaofan Yang, Saraschandra Naraginti, Yi Wang.  (2025)  A novel fluorescent sensing strategy for point-of-care monitoring of Hg2 +-induced oxidative stress in HeLa cells, zebrafish and mice models.  SENSORS AND ACTUATORS B-CHEMICAL,      [PMID:] [10.1016/j.snb.2025.137956]

32. Qingrui Zeng, Ziang Jia, Yingyang Song, Yiwen Fan, Xu Liu, Jinping Cheng.  (2025)  Novel ketone-based IPDA phase change absorbents for highly efficient wide-concentration-range CO2 capture and low-energy regeneration.  Engineering,      [PMID:] [10.1016/j.eng.2025.05.008]

33. Meili Yang, Zuzhe Kang, Xinpei Zhong, Sirui Bai, Dong-En Wang, Qin Tu, Sheng Chen, Jinyi Wang, Mao-Sen Yuan.  (2025)  Visualizing GSH-ONOO− Redox and Tracking Lesion-Remedy of Acute Kidney Oxidative Injury Based on a Dual-Site Chemosensor.  Advanced Healthcare Materials,      [PMID:40424091] [10.1002/adhm.202500907]

34. Hao Song, Liang Yi, Lixiang Huang, Wajid Ali, Linhan Cai, Chao Wang, Jianhua Huang, Ziwei Li, Anlian Pan.  (2026)  Meter-Scale Ultra-Large-Area Flexible Electroluminescent Devices Enabled by Aerosol Spraying.  Advanced Science,      [PMID:41588697] [10.1002/advs.202523831]