1.6 参考文献
1) 長谷川香料株式会社, 香料の科学, 講談社, 2013.
2) 堀内哲嗣郎, 香り創りをデザインする－調香の基礎からフレグランスの応用まで－, フレグランスジャーナル社, 2010.
3) 日本香料工業会 香料統計, https://www.jffma-jp.org/profile/statistics.html (2020 年 12 月 16日).
4) Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. ウォーレン有機化学 上, 東京化学同人,2003.
5) 牛田智, 藍染めを化学の視点から, 化学と教育, 2016, 64, 406–407.
6) 緒方直哉, カローザスのナイロンの合成, 高分子, 2007, 56, 14–15.
7) Ohashi, T.; Miyazawa, Y.; Ishizaki, S.; Kurobayashi, Y.; Saito, T. Identification of odor-active trace compounds in blooming flower of damask rose (Rosa damascena). J. Agric. Food Chem. 2019, 67, 7410–7415.
8) 中西啓, 天然感を増強させる微量重要香気成分の解明とその有用性に関する研究, 東京農業大学博士論文, 2017.
9) Ullrich, F.; Grosch, W. Identification of the most intense volatile flavor compounds formed during autoxidation of linoleic acid. Z. Lebensm. Unters. Forsch. 1987, 184, 277–282.
10) Schieberle, P.; Grosch, W. Evaluation of the flavour of wheat and rye bread crusts by aroma extract dilution analysis. Z. Lebensm. Unters. Forsch. 1987, 185, 111–113.
11) de Nicolaï P. A smelling trip into the past: The influence of synthetic materials on the history of perfumery. Chem. Biodivers. 2008, 5, 1137–1146.
12) Goeke, A.; Kraft, P.; Laue, H.; Zou, Y.; Volrol, F. 3-(4-Isobutyl-2-methylphenyl)propanal as perfume ingredient. WO 2014/180945 A1, (May 8, 2013).
13) 高井英司, 安田真紀, 冨川善彦, シトラール由来の新規オフフレーバー成分, 香りの本,2007, 233, 97–106.
14) 宮沢紀雄, 渡辺広幸, 櫻井毅彦, ゲラニル誘導体, 特開 2006-290843, (2005 年 4 月 15 日).
15) 公益社団法人 日本食品化学研究振興財団 指定添加物リスト (規則別表第 1), https://www.ffcr.or.jp/tenka/list/post-11.html (2021 年 1 月 6 日).
16) 公益社団法人 日本食品化学研究振興財団 指定添加物リスト (18 類の分類に該当する香料リスト), https://www.ffcr.or.jp/tenka/list/post-140.html (2021 年 1 月 6 日).
17) 公益社団法人 日本食品化学研究振興財団 天然香料基原物質リスト, http://www.ffcr.or.jp/tenka/list/post13.html?OpenDocument (2021 年 1 月 6 日).
2.6 参考文献
1) Gϋntert, M.; Brϋning, J.; Emberger, R.; Köpsel, M.; Kuhn, W.; Thielmann, T.; Werkhoff, P. Identification and formation of some selected sulfur-containing flavor compounds in various meat model systems. J. Agric. Food Chem. 1990, 38, 2027–2041.
2) Hofmann, T.; Schieberle, P.; Grosch, W. Model studies on the oxidative stability of odor-active thiols occurring in food flavors. J. Agric. Food Chem. 1996, 44, 251–255.
3) McIntosh, J. M.; Siddiqui, M. A. 2-Mercaptoaldehyde dimers and 2,5-dihydrothiophenes from 1,3-oxathiolan-5-one. Can. J. Chem. 1983, 61, 1872–1875.
4) MacLeod, G.; Seyyedain-Ardebili, M.; MacLeod, J. Substituted 4-methyl-1,3-dioxolanes: Solvent interaction products in some commercial beef flavorings. J. Agric. Food Chem. 1980, 28, 441–446.
5) Hartman, G. J.; Scheide, J. D.; Ho, C. T. Formation of volatile compounds from the reaction of leucine and D-glucose in propylene glycol. Perfum. Flavor. 1984, 8, 81–86.
6) Shahzadi, P.; Muhammad, A.; Mehmood, F.; Chaudhry, M. Y. Synthesis of 3,7-dimethyl-2,6-octadienal acetals from citral extracted from lemon grass, Cymbopogon citrates L. J. Antivir. Antiretrovir. 2013, 6, 28–31.
7) Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. ウォーレン有機化学 上, 東京化学同人, 2003.
8) Zheng, T.-C.; Burkart, M.; Richardson, D. E. A general and mild synthesis of thioesters and thiols from halides. Tetrahedron Lett. 1999, 40, 603–606.
9) Wuts, P. G. M. Greene’s protective groups in organic synthesis. Wiley, 2014.
10) Yiannios, C. N.; Karabinos, J. V. Oxidation of thiols by dimethyl sulfoxide. J. Org. Chem. 1963, 28, 3246–3248.
11) Tamura, H.; Fujita, A.; Steinhaus, M.; Takahisa, E.; Watanabe, H.; Schieberle, P. Assessment of the aroma impact of major odor-active thiols in pan-roasted white sesame seeds by calculation of odor activity values. J. Agric. Food Chem. 2001, 59, 10211–10218.
12) 岩崎好陽, 新訂 臭気の嗅覚測定法 三点比較式臭袋法測定マニュアル, 社団法人におい・かおり環境協会, 2005.
3.6 参考文献
1) Ohashi, T.; Miyazawa, Y.; Ishizaki, S.; Kurobayashi, Y.; Saito, T. Identification of odor-active trace compounds in blooming flower of damask rose (Rosa damascena). J. Agric. Food Chem. 2019, 67, 7410–7415.
2) Takahashi, S. New synthetic route to 3-substituted furanes; Synthesis of perillene and dendrolasin. Synth. Commun. 1976, 6, 331–337.
3) Tarui, H.; Mori, N.; Nishida, R.; Okabe, K.; Kuwahara, Y. 3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-acariolide and 4-(4-methyl-3-pentenyl)-2(5H)-furanone, α,β-acariolide: New monoterpene lactones from the astigmatid mites, Schwiebea araujoae and Rhizoglyphus sp. (Astigmata: Acaridae). Biosci. Biotecnol. Biochem. 2002, 66, 135–140.
4) Brenna, E.; Fuganti, C.; Serra, S.; Kraft, P. Optically active ionones and derivatives: Preparation and olfactory properties. Eur. J. Org. Chem. 2002, 6, 967–978.
5) Bugoni, S.; Merlini, V.; Porta, A.; Gaillard, S.; Zanoni, G.; Nolan, S. P.; Vidari, G. Competitive gold-promoted Meyer-Schuster and oxy-Cope rearrangements of 3-acyloxy-1,5-enynes: Selective catalysis for the synthesis of (+)-γ-ionone and (−)-(2S,6R)-cis-γ-irone. Chem. Eur. J. 2015, 21, 14068–14074.
6) 印藤元一, 合成香料 化学と商品知識, 化学工業日報社, 2005.
7) The good scents company information system, http://www.thegoodscentscompany.com/data/rw1035361.html (2021 年 1 月 17 日)
8) Elsharif, S. A.; Buettner, A. Structure-odor relationship study on geraniol, nerol, and their synthesized oxygenated derivatives. J. Agric. Food Chem. 2018, 66, 2324–2333.
9) Johnson, B. A.; Ong, J.; Lee, K.; Ho, S. L.; Arguello, S.; Leon, M. Effects of double and triple bonds on the spatial representations of odorants in the rat olfactory bulb. J. Comp. Neurol. 2007, 500, 720–733.
10) Pettersson, T.; Eklund, A.-M.; Wahlberg, I. New lactones from tobacco. J. Agric. Food Chem. 1993, 41, 2097–2103.
11) Yang, N.-N.; Ma, Q.-Y.; Huang, S.-Z.; Kong, F.-D.; Dai, H.-F.; Yu, Z.-F.; Zhao, Y.-X. Chemical study of the fungus Psilocybe merdaria. J. Asian. Nat. Prod. Res. 2017, 19, 333–338.
12) Bohlmann, F.; Zdero, C.; King, R. M.; Robinson, H. The first acetylenic monoterpene and other constituents from Senecio clevelandii. Phytochemistry 1981, 20, 2425–2427.
13) Gadir, S. A.; Smith, Y.; Taha, A. A.; Thaller, V. Isolation and synthesis of scobinolide, a new monoterpene lactone from cultures of the fungus Psathyrella scobinacea (Fr.) Konr. and Maubl. J. Chem. Res. Synop. 1986, 102–103.
4.6 参考文献
1) Winter, M. Odor and constitution. XIX. Homologs and analogs of 1-(p-hydroxyphenyl)-3-butanone (raspberry ketone). Helv. Chim. Acta. 1961, 44, 2110–2121.
2) Schulte-Elte, K. H.; Giersch, W.; Winter, B.; Pamingle, H.; Ohloff, G. Diastereoselektivität der geruchswahrnehmung von alkoholen der iononreihe [Diastereoselective odor perception of alcohols in the ionone series]. Helv. Chim. Acta. 1985, 68, 1961–1985. German.
3) Schulte-Elte, K. H.; Margot, C.; Chapuis, C.; Simmons, D. P.; Reichlin D. Optically active aliphatic alcohols and their use as perfuming ingredients. US 006054426A, (April 25, 2000).
4) The good scents company information system, http://www.thegoodscentscompany.com/data/rw1050771.html (2021 年 1 月 19 日)
5) Anselmi, C.; Centini, M.; Mariani, M.; Napolitano, E.; Sega, A.; Pelosi, P. Synthesis of ethers related to some floral odorants: Effect of oxygen/carbon replacement. J. Agric. Food Chem. 1994, 42, 2876–2879.
6) Kraft, P.; Bajgrowicz, J. A.; Denis, C.; Fráter, G. Odds and trends: Recent developments in the chemistry of odorants. Angew. Chem. Int. Ed. 2000, 39, 2980–3010.
7) de Nicolaï P. A smelling trip into the past: The influence of synthetic materials on the history of perfumery. Chem. Biodivers. 2008, 5, 1137–1146.
8) Devi, J. R.; Bhattacharyya, P. K. Microbiological transformations of terpenes: part XXIII– fermentation of geraniol, nerol & limonene by a soil pseudomonad, Pseudomonas incognita (linalool strain). Indian J. Biochem. Biophys. 1977, 14, 288–291.
9) Tarui, H.; Mori, N.; Nishida, R.; Okabe, K.; Kuwahara, Y. 3-(4-Methyl-3-pentenyl)-2(5H)-furanone, α,α-acariolide and 4-(4-methyl-3-pentenyl)-2(5H)-furanone, α,β-acariolide: New monoterpene lactones from the astigmatid mites, Schwiebea araujoae and Rhizoglyphus sp. (Astigmata: Acaridae). Biosci. Biotechnol. Biochem. 2002, 66, 135–140.
10) Sato, T.; Yoshimatsu, K.; Otera, J. CsF in organic synthesis. Efficient O-alkylation of tetronic acids. Synlett 1995, 8, 843–844.
11) Corey, E. J.; Schmidt, G. A simple route to Δ2-butenolides from conjugated aldehydes. Tetrahedron Lett. 1980, 21, 731–734.
12) Freirίa, M.; Whitehead, A. J.; Tocher, D. A.; Motherwell, W. B. Further observations on the rhodium (I)-catalysed tandem hydrosilylation-intramolecular aldol reaction. Tetrahedron 2004, 60, 2673–2692.
13) Vickers, T. Intramolecular Heck reactions with dihydropyrans: Synthesis of (+/-)-curcumene ether. Ph.D. thesis. University of Calgary, 2002.
14) Morino, A.; Kuwahara, Y.; Matsuyama, S.; Suzuki, T. (E)-2-(4’-Methyl-3’-pentenylidene)-4-butanolide, named β-acariolide: A new monoterpene lactone from the mold mite, tyrophagus putrescentiae. (Acarina: Acaridae). Biosci. Biotecnol. Biochem. 1997, 61, 1906–1908.
15) Brito, G. A.; Sarotti, A. M.; Wipf, P.; Pilli, R. A. Cascade cyclization triggered by imine formation. Formal synthesis of the alkaloid (±)-stemoamide and its 9a-epimer. Tetrahedron Lett. 2015, 56, 6664–6668.
16) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. Olefin homologation with titanium methylene compounds. J. Am. Chem. Soc. 1978, 100, 3611–3613.
17) Figueredo, M.; Font, J.; Virgili, A. Studies on structurally simple α,β-butenolides. VII. An easy entry to γ-thiomethyl- and γ-aminomethyl-α,β-butenolides. Tetrahedron 1987, 43, 1881–1886.
18) Busqué, F.; March, P.; Figueredo, M. Font, J.; Margaretha, P.; Raya, J. Regioselectivity of the intramolecular photocycloaddition of α,β-butenolides. Synthesis 2001, 8, 1143–1148.
19) Hodgson, D. M.; Chung, Y. K.; Paris, J.-M. Intramolecular cyclopropanation of unsaturated terminal epoxides. J. Am. Chem. Soc. 2004, 126, 8664–8665.
20) Peil, S.; Guthertz, A.; Biberger, T.; Fürstner, A. Hydrogenative cyclopropanation and hydrogenative metathesis. Angew. Chem. Int. Ed. 2019, 58, 8851–8856.
21) Reich, H. J.; Chow, F.; Shah, S. K. Selenium stabilized carbanion. Preparation of α-lithio selenides and applications to the synthesis of olefins by reductive elimination of β-hydroxy selenides and selenoxide syn elimination. J. Am. Chem. Soc. 1979, 101, 6638–6648.
22) Ohashi, T.; Miyazawa, Y.; Ishizaki, S.; Kurobayashi, Y.; Saito, T. Identification of odor-active trace compounds in blooming flower of damask rose (Rosa damascena). J. Agric. Food Chem. 2019, 67, 7410–7415.
23) Yang, B.; Lu, Z. Visible-light-promoted oxidative [4+2] cycloadditions of aryl silyl enol ethers. J. Org. Chem. 2016, 81, 7288–7300.
24) Salomon, R. G.; Coughlin, D. J.; Ghosh, S.; Zagorski, M. G. Copper(I) catalysis of olefin photoreactions. 9. Photobicyclization of α-, β-, and γ-alkenylallyl alcohols. J. Am. Chem. Soc. 1982, 104, 998–1007.
25) Williams, C. M.; Mander, L. N. Chromatography with silver nitrate. Tetrahedron 2001, 57, 425– 447.
26) Hwang, Y. C.; Fowler, F. W. Diels-Alder reaction of 1-azadienes. A total synthesis of deoxynupharidine. J. Org. Chem. 1985, 50, 2719–2726.
27) Katae, T.; Sugiyama, S.; Satoh, T. Multisubstituted α,β-unsaturated γ-lactones from 1-chlorovinyl p-tolyl sulfoxides and tert-butyl carboxylates using Pummerer-type cyclization as the key reaction. Synthesis 2011, 9, 1435–41.
5.6 参考文献
1) Guth, H.; Grosch, W. 3-Methylnonane-2,4-dione – An intense odour compound formed during flavor reversion of soya-bean oil. Fat Sci. Technol. 1989, 91, 225–230.
2) Bajgrowicz, J. A.; Frank, I.; Fráter, G. Synthesis and structure elucidation of a new potent sandalwood-oil substitute. Helv. Chim. Acta. 1998, 81, 1349–1358.
3) Kiyota, H.; Higashi, E.; Koike, T.; Oritani, T. Syntheses and odour descriptions of jasmine lactone and cis-jasmone analogues bearing cyclopropane moieties. Flavour Fragr. J. 2001, 16, 175– 179.
4) Sakauchi, H.; Asao, H.; Hasaba, T.; Kuwahara, S.; Kiyota, H. Syntheses and odor descriptions of cyclopropanated compounds. Chem. Biodivers. 2006, 3, 544–552.
5) https://www.soda.co.jp/business/synthetic/syn_001.html (2021 年 1 月 27 日).
6) Tateba, H.; Mihara, S. Structure-odor relationships in monoterpenelactone. Agric. Biol. Chem. 1990, 54, 2271–2276.
7) Ohashi, T.; Miyazawa, Y.; Ishizaki, S.; Kurobayashi, Y.; Saito, T. Identification of odor-active trace compounds in blooming flower of damask rose (Rosa damascena). J. Agric. Food Chem. 2019, 67, 7410–7415.
8) Zhang, G.; Zhang, L. Au-containing all-carbon 1,3-dipoles: Generation and [3+2] cycloaddition reactions. J. Am. Chem. Soc. 2008, 130, 12598–12599.
9) Schneider, J. A.; Yoshihara, K. Facile and highly effective synthesis of (−)-mevalonic-2-d and -4-d acid lactones. J. Org. Chem. 1986, 51, 1077–1079.
6.6 参考文献
1) Kost, B.; Matysiak, S.; Kula, J.; Bonikowski, R. Synthesis of thiophene derivatives with long-lasting citrusy type odour. Flavour Fragr. J. 2018, 33, 279–284.
2) Dia, R.-M.; Belaqziz, R.; Romane, A.; Antoniotti, S.; Duñach, E. Flavouring and odorant thiols from renewable natural resources by InIII-catalyzed hydrothioacetylation and lipase-catalyzed solvolysis. Tertahedron Lett. 2010, 51, 2164–2167.
3) Agyemang, D. O.; Brain, A. V. K.; Cai, T.; Cannon, R. J.; Chen, M. Z.; Curto, N. L.; Janczuk, A. J.; Jones, P. D.; Kazimierski, A.; Li, J.; Rodriguez, D. Thiophenylethanol and octenol derivatives as organoleptic compounds and their preparation and use in flavor and fragrance compositions. WO 2015/157153 A1 (October 15, 2015).
4) Fehr, C.; Galindo, J. Aldols by Michael addition: Application of the retro-Michael addition to the slow release of enones. Helv. Chim. Acta. 2005, 88, 3128–3136.
5) Maddalena, U.; Trachsel, A.; Fankhauser, P.; Berthier, D. L.; Benczédi, D.; Wang, W.; Xi, X.; Shen, Y.; Herrmann, A. Thioether profragrances: Parameters influencing the performance of precursor-based fragrance delivery in functional perfumery. Chem. Biodivers. 2014, 11, 1700–1733.
6) Gross, P.; Sperl, G.; Pamukcu, R.; Brendel, K. Lactone compounds for treating patient with precancerous lesions. US patent. 5776962 (Jun 7, 1998).
7) Busqué, F.; de March, P.; Figueredo, M.; Font, J.; González, L. A study of the conjugate addition of thionucleophiles to 2(5H)-furanones. Eur. J. Org. Chem. 2004, 2004, 1492–1499.
8) Cao, L. Seven- and eight-membered ether formation via sulfonium ylide rearrangement processes and application in an approach to (+)-laurencin. Ph.D. Thesis, University of Alberta, 2010.
9) Nishide, K.; Ohsugi, S.; Miyamoto, T.; Kumar, K.; Node, M. Development of odorless thiols and sulfides and their applications to organic synthesis. Monatsh. Chem. 2004, 135, 189–200.
10) Tamura, H.; Fujita, A.; Steinhaus, M.; Takahisa, E.; Watanabe, H.; Schieberle, P. Assessment of the aroma impact of major odor-active thiols in pan-roasted white sesame seeds by calculation of odor activity values. J. Agric. Food Chem. 2011, 59, 10211–10218.
11) Ohashi, T.; Miyazawa, Y.; Ishizaki, S.; Kurobayashi, Y.; Saito, T. Identification of odor-active trace compounds in blooming flower of damask rose (Rosa damascena). J. Agric. Food Chem. 2019, 67, 7410–7415.
12) Labruère, R.; Desbène-Finck, S.; Helissey, P.; Giorgi-Renault, S. Efficient syntheses of thiono and dithio analogues of tetronic acid. Synthesis 2006, 24, 4163–4166.
13) Egorova, A. Y.; Sedavkina, V. A.; Morozova, N. A. Thionylation of 5-alkyl-3H-furan-2-ones and their non-cyclic 4-oxoalkanoate ester analogs. Chem. Heterocycl. Compd. (NY). 1999, 35, 41–44.
14) Bongards, C.; Gärtner, W. Synthesis of hetero atom modified pyrromethenones. Eur. J. Org. Chem. 2007, 5749–5758.
15) Araki, S.; Butsugan, Y. Regio-controlled prenylation and geranilation of 3-furylmethylmagnesium bromide. Selective syntheses of 3-substituted furanoid and 2-substituted 3-methylfuranoid terpenes. Bull. Chem. Soc. Jpn. 1983, 56, 1446–1449.
16) Atack, T. C.; Lecker, R. M.; Cook, S. P. Iron-catalyzed borylation of alkyl electrophiles. J. Am. Chem. Soc. 2014, 136, 9521–9523.
17) Coevers, A.; van Mil, J. H.; Sap, M. M. E.; Buck, H. M. Synthesis of thiophene-containing steroid-like molecules via olefinic cyclization reactions. Recul. Trav. Chim. Pays-Bas 1977, 96, 18– 22.
18) Nitti, A.; Signorile, M.; Boiocchi, M.; Bianchi, G.; Po, R.; Pasini, D. Conjugated thiophene-fused isatin dyes through intramolecular direct arylation. J. Org. Chem. 2016, 81, 11035– 11042.
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