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Scheme 1: Synthesis of (-)-menthol
Symrise is one of the global leaders in the production of synthetic L-menthol, and with this acquisition is substantially strengthening its competitiveness in this particular field.
22, 2013) by Yelm et al., assigned to Procter & Gamble, entitled SYNTHESIS OF CYCLOHEXANE DERIVATIVES USEFUL AS SENSATES IN CONSUMER PRODUCTS, a series of Neomenthyl esters and ethers were disclosed that had cooling properties as good as, or better, than the coresponding menthyl isomers.
The synthesis of a menthol derivative of 2-aminopurine …
Haught, entitled Synthesis of Cyclohexane Derivatives Useful as Sensates in Consumer Products which explores the synthesis and sensory properties of various Neo-menthane carboxamides (including the Neo isomer (1S,2S,5R)-N-(4-(cyanomethyl)phenyl)-2-isopropyl-5-methylcyclohexanecarboxamide, Neo G-180). Th
See Claudio Fuganti, Daniel Joulain, Francesco Maggioni, Luciana Malpezzi, Stefano Serra, Andrea Vecchione, 3-Alkyl-p-menthan-3-ol derivatives: synthesis and evaluation of their physiological cooling activity, D.
Synthesis and properties of new (−)-menthol-derived …
Menthol has also been manufactured synthetically since 1973. In chemical terms, it is a cyclic hydrocarbon with an alcohol group which at room temperature is a colorless solid. Previous chemical production methods, however, have certain disadvantages: either they require very complex, multi-step syntheses, or they yield not only the desired, naturally occurring L-menthol but also the same amount of a by-product called D-menthol which, depending on the intended use, has to be laboriously removed from the mixture. L- and D-menthol are variants of the same molecule, but have a mirror-image structure in relation to each other, like the right and left hand. Scientists call these molecules "enantiomers". The different structure means that L- and D-menthol have different effects in the body. D-menthol, for example, has a less pronounced cooling action. A mixture of the two variants, known as DL-menthol, is required mainly for products in which the cooling effect is not predominant, for example in certain flavoring ingredients.
BASF has now developed a new process based on the aroma chemical citral which is already produced in BASF's Verbund system. "One of the key steps in the new process is called asymmetric hydrogenation," explains BASF research scientist Dr. Rocco Paciello. "For this purpose we have developed a special, highly efficient catalyst system which ensures that mainly just a certain enantiomer is synthesized from the citral." In two further synthesis steps, this intermediate is then used to produce the L-menthol. Another advantage of this technique: it is a continuous process in which substances are constantly added and removed so therefore it has no downtimes. This not only saves time but is more resource-efficient because more L-menthol with a purity of at least 99.7 percent can be produced using the same amount of starting materials.
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