Terpenoids

Abstract

Terpenes are found in essential oils and oleoresins of plants. Terpenes found in turpentine are used as raw materials for the commercial synthesis of a wide range of aroma chemicals. Uses for the monoterpenes are covered in more depth than the higher terpenes mainly because of the large fragrance industry that developed from the availability of sulfate turpentine from the paper industry. α‐ and β‐Pinene, the predominant terpenes found in turpentine, are used to manufacture other hydrocarbons such as myrcene, dihydromyrcene, alloocimene, camphene, p ‐menthadienes, and p ‐cymene. These hydrocarbons are used in turn as raw materials for producing products such as pine oil, nerol and geraniol, citronellol, linalool, menthol, campholenic aldehyde, citral, ionones and methyl ionones, camphor, citronellal, and hydroxycitronellal. Methods employing petrochemical‐based raw materials such as acetone, acetylene, isobutylene, and isoprene have become very important commercial processes. Intermediates such as linalool, geranyl acetone, and citral for synthesis of Vitamins A and E are produced in large scale. The processes also yield linalool, citronellol, citronellal, and citral for fragrance uses as well as for intermediates for synthesis of many other aroma products. Sesquiterpenes derived from natural sources are used as such for fragrance materials and for synthesis of other products. Sesquiterpenes covered include caryophyllene, longifolene, cedrene and cedrol, nerolidol and farnesol, α‐bisabolol, α‐santalol, valencene, nootkatene and nootkatone, patchouli alcohol, and guaiol and bulnesol. Diterpenes such as gibberellic acid, phytol and isophytol, and taxol are discussed as are the triterpenes, lanosterol and squalene. The commercial aspects of the important group of tetraterpenes, the carotenoids, are also covered.

Killer strains ofSaccharomyces: application for apple wine production

“…The compounds 3‐hepten‐2‐one and 6‐methyl‐5‐hepten‐2‐one were detected only in the samples fermented by S. paradoxus ; 3‐methyl‐butanal and myrac aldehyde were characteristic for S. cerevisiae samples; 3,5,5‐trimethyl‐2(5H)‐furanone was characteristic for the S. capensis wines. Some of these are products of carotenoid catabolism , while other are formed from terpenoids .…”

Catalytic performance of Metal-Organic-Frameworks vs. extra-large pore zeolite UTL in condensation reactions

“…Prins reaction, involving the electrophilic addition of an activated paraformaldehyde (PF) to β-pinene, leads to the formation of nopol (6,6-dimethylbicyclo[3.1.1]hept-2-ene-2-ethanol), an optically active bicyclic primary alcohol, useful in the agrochemical industry to produce pesticides, soap perfumes, detergents and polishes (Bledsoe, 1997 ) (Scheme 3 ). Hydrochloric acid, alkyl-substituted aluminum chlorides (Williams et al, 2002 ), SnCl 4 (Andersen et al, 1985 ), InCl 3 (Yadav et al, 2003 ), and heteropolyacids (Li et al, 2004 ) are typically used to catalyze Prins reaction in homogeneous systems.…”

Covalent Organic Framework Decorated with Vanadium as a New Platform for Prins Reaction and Sulfide Oxidation

“…Prins-type cyclization is used to synthesize nopol, an important bicyclic primary alcohol used in agrochemical industry to form pesticide, detergents, perfumes, etc. , Two most common ways to synthesize nopol in homogenous system are either by using ZnCl 2 at 115 °C or CH 3 COOH at 120 °C followed by saponification of nopyl acetate to nopol and reaction of paraformaldehyde and β-pinene in an autoclave at 150–230 °C. , To avoid longer reaction time, higher temperature and pressure and more importantly, opening the door for green synthetic routes, stable heterogeneous catalysts such as zeolites, metal–organic frameworks, MCM-41, Sn-SBA-15 are used for Prins reaction. , In addition, the profound role of sulphoxide in chemical and medicinal industries makes the conversion of sulfide to sulphoxide in presence of oxidizing agent, an extremely important reaction . Many oxidants such as MnO 2 , RuO 4 , NMO with OSO 4 and others are most common to perform this key transformation.…”