Chemistry:Nopol
Nopol is a semi-synthetic bicyclic monoterpenoid alcohol with the molecular formula C
11H
18O. It is a colorless viscous liquid at room temperature. Nopol has a woody, camphoraceous odor and is used in fragrances and flavorings. As a chiral compound, it can exist in either of two enantiomeric forms, (−)-nopol and (+)-nopol.
Synthesis
Nopol is typically synthesized via the Prins reaction of β-pinene with paraformaldehyde.[1][2] Syntheses using materials such as tin silicate catalysts have also been reported for selective production.[3][4]
Uses
Nopol is used in the fragrance industry for its balsamic, pine-like scent in soaps, detergents, and household products.[5] It serves as an intermediate in the synthesis of pesticides and agrochemicals. Derivatives of nopol, such as nopyl acetate, are employed in perfumery and as fuel additives.[6][7][8] Nopol and its derivatives exhibit antifungal, insecticidal, and other bioactivities.[9]
References
- ↑ J. P. Bain (1946). "Nopol. I. The Reaction of β-Pinene with Formaldehyde". Journal of the American Chemical Society 68 (4). doi:10.1021/ja01208a032.
- ↑ Sumit V. Jadhav, Krishna Mohan Jinka, Hari C. Bajaj (2010). "Synthesis of nopol via Prins condensation of β-pinene and paraformaldehyde catalyzed by sulfated zirconia". Applied Catalysis A: General 390 (1–2): 158–165. doi:10.1016/j.apcata.2010.10.005.
- ↑ M. Selvaraj and P. K. Sinhab (2010). "Highly selective and clean synthesis of nopol over well-ordered mesoporous tin silicate catalysts". New J. Chem. 34: 1921–1929. doi:10.1039/C0NJ00080A.
- ↑ Aída Luz Villa de P, Edwin Alarcón, Consuelo Montes de C (2005). "Nopol synthesis over Sn-MCM-41 and Sn-kenyaite catalysts". Catalysis Today 107–108: 942–948. doi:10.1016/j.cattod.2005.07.049.
- ↑ Cite error: Invalid
<ref>tag; no text was provided for refs namedthegoodscentscompany - ↑ "Introduction of Nopol and Nopyl acetate". Foreverest Resources Ltd. https://foreverest.net/news-list/introduction-of-nopol-and-nopyl-acetate.
- ↑ Surburg, Horst; Panten, Johannes (2016). Common fragrance and flavor materials: preparation, properties and uses (6 ed.). Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA. ISBN 978-3-527-33160-4.
- ↑ Opdyke, D. L. J. (2013-10-22) (in en). Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology. Elsevier. ISBN 978-1-4831-4797-0. https://books.google.com/books?id=IDkvBQAAQBAJ.
- ↑ Ming Chen, Wen-Gui Duan, Gui-Shan Lin, Zhong-Tian Fan, Xiu Wang (2021). "Synthesis, Antifungal Activity, and 3D-QSAR Study of Novel Nopol-Derived 1,3,4-Thiadiazole-Thiourea Compounds". Molecules 6 (6): 1708. doi:10.3390/molecules26061708.
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