Synthesis, Characterization, and Perfumery Application of Acetal Derivatives of 2-Methyl-3-(4-R-Phenyl) Propanal: A Short Review
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Keywords:acetal derivatives, acetalization, synthesis, characterization, perfume ingredients
Perfumes and fragrances are seen as an essential part of life in many countries, and many men and women use perfumes regularly. Originally, the perfume ingredients were derived from natural sources such as essential oils. However, these natural ingredients encountered challenges, such as poor crop quality, a limited supply of supplies, or difficulties using plant or animal extracts. Hence, with the development of synthetic organic chemistry in the 19th century, many ingredients were produced synthetically, resulting from the creativity of laboratory chemists, and used in today’s perfumes. Acetal is one of the synthetic aromatic chemicals used as ingredients in perfume nowadays. This paper review focuses on synthesis and characterization techniques for analyzing acetal derivatives of 2-methyl-3- (4-R-phenyl)propanal and their perfumery application, such as odor characteristics.
Chisvert, Alberto, Marina López-Nogueroles, Pablo Miralles, and Amparo Salvador. 2018. “Perfumes in Cosmetics.” Analysis of Cosmetic Products, 225–48. https://doi.org/10.1016/b978-0-444-63508-2.00010-2.
Angelucci, F. L., V. V. Silva, C. Dal Pizzol, L. G. Spir, C. E. O. Praes, and H. Maibach. 2014. “Physiological Effect of Olfactory Stimuli Inhalation in Humans: An Overview.” International Journal of Cosmetic Science 36 (2): 117–23. https://doi.org/10.1111/ics.12096
Rachel S. Herz, Neurobiology of Sensation and Reward. Taylor and Francis Group, 2011.
Séquin, M. 2017. “Volatiles for the Perfume Industry.” Encyclopedia of Applied Plant Sciences, 393–98. https://doi.org/10.1016/b978-0-12-394807-6.00089-7.
T. W. Graham Solomons, C. B. Fryhle, and S. A. Snyder, Solomons’ Organic Chemistry, 12th ed. Singapore: John Wiley & Sons, 2016.
Teixeira, Miguel A., Oscar Rodríguez, Vera G. Mata, and Alírio E. Rodrigues. 2009. “The Diffusion of Perfume Mixtures and the Odor Performance.” Chemical Engineering Science 64 (11): 2570–89. https://doi.org/10.1016/j.ces.2009.01.064.
Vyglazov, O. G., V. A. Chuiko, L. V. Izotova, Zh. V. Vintarskaya, and R. Ya. Yudenko. 2001. “Synthesis and Perfume Characteristics of Acetals Containing an Aromatic Ring.” Russian Journal of Applied Chemistry 74 (11): 1888–91. https://doi.org/10.1023/a:1014848929083
J. P. Horst Surburg, Common Fragrance and Flavor Materials: Preparation, Properties and Uses, 6th Edition. Wiley VCH Verlag GmbH & Co. KGaA, 2016.
Genva, Manon, Tierry Kenne Kemene, Magali Deleu, Laurence Lins, and Marie-Laure Fauconnier. 2019. “Is It Possible to Predict the Odor of a Molecule on the Basis of Its Structure?” International Journal of Molecular Sciences 20 (12). https://doi.org/10.3390/ijms20123018.
Chisvert, Alberto, Marina López-Nogueroles, and Amparo Salvador. 2018. “Perfumes.” Reference Module in Chemistry, Molecular Sciences and Chemical Engineering. https://doi.org/10.1016/b978-0-12-409547-2.14037-5.
Shahzadi, Phool, Ali Muhammad, Ferhat Mehmood, and Muhammad Yasir Chaudhry. 2014. “Synthesis of 3, 7-Dimethyl-2, 6-Octadienal Acetals from Citral Extracted from Lemon Grass, Cymbopogon Citrates L.” Journal of Antivirals & Antiretrovirals 06 (01): 28-31. https://doi.org/10.4172/jaa.1000091.
Kumar, Komal, Shailesh Pathak, and Sreedevi Upadhyayula. 2021. “Acetalization of 5-Hydroxymethyl Furfural into Biofuel Additive Cyclic Acetal Using Protic Ionic Liquid Catalyst- a Thermodynamic and Kinetic Analysis.” Renewable Energy 167 (April): 282–93. https://doi.org/10.1016/j.renene.2020.11.084.
K. Burger, “Evaluation of Eucalyptus Citriodora Derived P- Methane-3,8-Diol-Citronellal Acetal as A Bio-Plasticizer For Cosmetic Applications.,” no. June, 2013.
Nikitas, Nikolaos F., Ierasia Triandafillidi, and Christoforos G. Kokotos. 2019. “Photo-Organocatalytic Synthesis of Acetals from Aldehydes.” Green Chemistry 21 (3): 669–74. https://doi.org/10.1039/c8gc03605e.
Karimi, Babak, and Behzad Golshani. 2002. “Iodine-Catalyzed, Efficient and Mild Procedure for Highly Chemoselective Acetalization of Carbonyl Compounds under Neutral Aprotic Conditions.” Synthesis 2002 (06): 784–88. https://doi.org/10.1055/s-2002-25775.
Smirnov, Andrey, Svetlana Selishcheva, and Vadim Yakovlev. 2018. “Acetalization Catalysts for Synthesis of Valuable Oxygenated Fuel Additives from Glycerol.” Catalysts 8 (12): 595. https://doi.org/10.3390/catal8120595.
Dong, Jian-Lian, Li-Si-Han Yu, and Jian-Wu Xie. 2018. “A Simple and Versatile Method for the Formation of Acetals/Ketals Using Trace Conventional Acids.” ACS Omega 3 (5): 4974–85. https://doi.org/10.1021/acsomega.8b00159.
Procuranti, Barbara, and Stephen J. Connon. 2008. “Unexpected Catalysis: Aprotic Pyridinium Ions as Active and Recyclable Brønsted Acid Catalysts in Protic Media.” Organic Letters 10 (21): 4935–38. https://doi.org/10.1021/ol802008m.
Myles, Lauren, Nicholas Gathergood, and Stephen J. Connon. 2013. “The Catalytic Versatility of Low Toxicity Dialkyltriazolium Salts: In Situ Modification Facilitates Diametrically Opposed Catalysis Modes in One Pot.” Chemical Communications 49 (46): 5316. https://doi.org/10.1039/c3cc41588k.
Myles, Lauren, Rohitkumar G. Gore, Nicholas Gathergood, and Stephen J. Connon. 2013. “A New Generation of Aprotic yet Brønsted Acidic Imidazolium Salts: Low Toxicity, High Recyclability and Greatly Improved Activity.” Green Chemistry 15 (10): 2740. https://doi.org/10.1039/c3gc40975a.
U. Azzena et al., “Ammonium Salts Catalyzed Acetalization Reactions in Green Ethereal Solvents,” pp. 1–18, 2020.
Nikitas, Nikolaos F., Petros L. Gkizis, and Christoforos G. Kokotos. 2021. “Thioxanthone: A Powerful Photocatalyst for Organic Reactions.” Organic & Biomolecular Chemistry 19 (24): 5237–53. https://doi.org/10.1039/d1ob00221j.
Liu, Peidang, Kewen He, Yinxia Li, Qiuli Wu, Peng Yang, and Dayong Wang. 2012. “Exposure to Mercury Causes Formation of Male-Specific Structural Deficits by Inducing Oxidative Damage in Nematodes.” Ecotoxicology and Environmental Safety 79 (May): 90–100. https://doi.org/10.1016/j.ecoenv.2011.12.007.
Ferreira, Gabriel, Charles Carvalho, and Shirley Nakagaki. 2019. “Studies of the Catalytic Activity of Iron (III) Porphyrins for the Protection of Carbonyl Groups in Homogeneous Media.” Catalysts 9 (4): 334. https://doi.org/10.3390/catal9040334.
Teschke, Rolf. 2018. “Liver Injury by Carbon Tetrachloride Intoxication in 16 Patients Treated with Forced Ventilation to Accelerate Toxin Removal via the Lungs: A Clinical Report.” Toxics 6 (2). https://doi.org/10.3390/toxics6020025.
Tanaka, Nobuo, Izumi Ogawa, Shigeki Yoshigase, and Junzo Nokami. 2008. “Regioselective Ring Opening of Benzylidene Acetal Protecting Group(S) of Hexopyranoside Derivatives by DIBAL-H.” Carbohydrate Research 343 (15): 2675–79. https://doi.org/10.1016/j.carres.2008.07.017.
Ranu, Brindaban C., Ranjan Jana, and Sampak Samanta. 2004. “A Simple, Efficient and General Procedure for Acetalization of Carbonyl Compounds and Deprotection of Acetals under the Catalysis of Indium(III) Chloride.” Advanced Synthesis & Catalysis 346 (4): 446–50. https://doi.org/10.1002/adsc.200303154.
Zhang, Yi, Zhaojie Wang, Xin Xu, Jun Gao, Dongmei Xu, Lianzheng Zhang, and Yinglong Wang. 2020. “Entrainers Selection and Vapour-Liquid Equilibrium Measurements for Separating Azeotropic Mixtures (Ethanol + N-Hexane/Cyclohexane) by Extractive Distillation.” The Journal of Chemical Thermodynamics 144 (May): 106070. https://doi.org/10.1016/j.jct.2020.106070.
Monticelli, Serena, Laura Castoldi, Irene Murgia, Raffaele Senatore, Eugenia Mazzeo, Judith Wackerlig, Ernst Urban, Thierry Langer, and Vittorio Pace. 2016. “Recent Advancements on the Use of 2-Methyltetrahydrofuran in Organometallic Chemistry.” Monatshefte Für Chemie - Chemical Monthly 148 (1): 37–48. https://doi.org/10.1007/s00706-016-1879-3.
Watanabe, Kiyoshi. 2013. “The Toxicological Assessment of Cyclopentyl Methyl Ether (CPME) as a Green Solvent.” Molecules 18 (3): 3183–94. https://doi.org/10.3390/molecules18033183.
Antonucci, Vincent, John Coleman, James B. Ferry, Neil Johnson, Michelle Mathe, Jeremy P. Scott, and Jing Xu. 2011. “Toxicological Assessment of 2-Methyltetrahydrofuran and Cyclopentyl Methyl Ether in Support of Their Use in Pharmaceutical Chemical Process Development.” Organic Process Research & Development 15 (4): 939–41. https://doi.org/10.1021/op100303c.
Watanabe, Kiyoshi, Noriyuki Yamagiwa, and Yasuhiro Torisawa. 2007. “Cyclopentyl Methyl Ether as a New and Alternative Process Solvent.” Organic Process Research & Development 11 (2): 251–58. https://doi.org/10.1021/op0680136.
Aycock, David F. 2006. “Solvent Applications of 2-Methyltetrahydrofuran in Organometallic and Biphasic Reactions.” Organic Process Research & Development 11 (1): 156–59. https://doi.org/10.1021/op060155c.
R. Sindhu, P. Binod, and A. Pandey, Microbial Poly-3- Hydroxybutyrate and Related Copolymers. Elsevier BV, 2015.
Wladislaw, B., A. Giora, and G. Vicentini. 1966. “The Syntheses and Infrared Spectra of Some Acetals and Ketals.” Journal of the Chemical Society B: Physical Organic, 586-588. https://doi.org/10.1039/j29660000586.
Pawar, Radheshyam R., Sumit V. Jadhav, and Hari C. Bajaj. 2014. “Microwave-Assisted Rapid Valorization of Glycerol towards Acetals and Ketals.” Chemical Engineering Journal 235 (January): 61–66. https://doi.org/10.1016/j.cej.2013.09.018.
Fadeeva, V. P., V. D. Tikhova, and O. N. Nikulicheva. 2008. “Elemental Analysis of Organic Compounds with the Use of Automated CHNS Analyzers.” Journal of Analytical Chemistry 63 (11): 1094–1106. https://doi.org/10.1134/s1061934808110142.
V. V. Coa, V. Lubes, J. Polster, M. M. de A. Silva, and G. Lubes. 2019. “Relationship between Structure and Odor,” Food Aroma Evolution, 679–694. doi: https://doi.org/10.1201/9780429441837- 31.
C. M. Mcginley, M. a Mcginley, and D. L. Mcginley, “Odor Basics, Understanding and Using Odor Testing,” 22nd Hawaii Water Environment Association Conference., pp. 6–7, 2000.
Gygax, Hansruedi, and Heinz Koch. 2001. “The Measurement of Odours.” CHIMIA 55 (5): 401. https://doi.org/10.2533/chimia.2001.401.
Wen, Tengteng, Dehan Luo, Jiafeng He, and Kai Mei. 2018. “The Odor Characterizations and Reproductions in Machine Olfactions: A Review.” Sensors 18 (7): 2329. https://doi.org/10.3390/s18072329.
G. Reineccius, Flavor Chemistry and Technology, 2nd Edition. CRC Press, 2016.
G. A. Burdock, Fenaroli’s Handbook of Flavor Ingredients, 6th Edition. CRC Press, 2010.
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