Background and purpose: Transient receptor potential (TRP) V3 is a thermosensitive ion channel expressed predominantly in the skin and neural tissues. It is activated by warmth and the monoterpene camphor and has been hypothesized to be involved in skin sensitization. A selection of monoterpenoid compounds was tested for TRPV3 activation to establish a structure-function relationship. The related channel TRPM8 is activated by cool temperatures and a number of chemicals, among them the monoterpene (-)-menthol. The overlap of the receptor pharmacology between the two channels was investigated. Experimental approach: Transfected HEK293 cells were superfused with the test substances. Evoked currents were measured in whole cell patch clamp measurements. Dose-response curves for the most potent agonists were obtained in Xenopus laevis oocytes. Key results: Six monoterpenes significantly more potent than camphor were identified: 6-tert-butyl-m-cresol, carvacrol, dihydrocarveol, thymol, carveol and ( þ )-borneol. Their EC 50 is up to 16 times lower than that of camphor. All of these compounds carry a ring-located hydroxyl group and neither activates TRPM8 to a major extent. Conclusions and implications: Terpenoids have long been recognized as medically and pharmacologically active compounds, although their molecular targets have only partially been identified. TRPV3 activation may be responsible for several of the described effects of terpenoids. We show here that TRPV3 is activated by a number of monoterpenes and that a secondary hydroxyl-group is a structural requirement.
The article contains sections titled: 1. Introduction 1.1. The Chemical Senses 1.2. Definition 1.3. History 1.4. Odor Descriptors, Odor Thresholds, Odor Value 1.4.1. Qualitative Measurements 1.4.2. Quantitative Measurements 1.4.2.1. Odor Threshold 1.4.2.2. Odor Value 1.5. Regulations and Labeling Requirements 1.5.1. Flavors 1.5.2. Fragrances 2. Single Fragrance and Flavor Compounds 2.1. Aliphatic Compounds 2.1.1. Hydrocarbons 2.1.2. Alcohols 2.1.3. Aldehydes and Acetals 2.1.4. Ketones 2.1.5. Acids and Esters 2.1.6. Miscellaneous Compounds 2.2. Acyclic Terpenes 2.2.1. Hydrocarbons 2.2.2. Alcohols 2.2.3. Aldehydes and Acetals 2.2.4. Ketones 2.2.5. Acids and Esters 2.2.5.1. Geranyl and Neryl Esters 2.2.5.2. Linalyl and Lavandulyl Esters 2.2.5.3. Citronellyl Esters 2.2.6. Miscellaneous Compounds 2.3. Cyclic Terpenes 2.3.1. Hydrocarbons 2.3.2. Alcohols and Ethers 2.3.3. Aldehydes and Ketones 2.3.4. Esters 2.3.5. Miscellaneous Compounds 2.4. Other Cycloaliphatic Compounds 2.4.1. Alcohols 2.4.2. Aldehydes 2.4.3. Ketones 2.4.4. Esters 2.5. Aromatic Compounds 2.5.1. Hydrocarbons 2.5.2. Alcohols and Ethers 2.5.3. Aldehydes and Acetals 2.5.4. Ketones 2.5.5. Esters of Araliphatic Alcohols and Aliphatic Acids 2.5.6. Aromatic Acids 2.5.7. Esters Derived from Aromatic and Araliphatic Acids 2.5.7.1. Benzoates 2.5.7.2. Phenyl acetates 2.5.7.3. Cinnamates 2.5.8. Miscellaneous Compounds 2.6. Phenols and Phenol Derivatives 2.6.1. Phenols, Phenyl Esters, and Phenyl Ethers 2.6.2. Phenol Alcohols and their Esters 2.6.3. Phenol Aldehydes 2.6.4. Phenol Ketones 2.6.5. Phenol Carboxylates 2.7. O‐ and O, S‐Heterocycles 2.7.1. Cyclic Ethers 2.7.2. Lactones 2.7.3. Glycidates 2.7.4. Miscellaneous Compounds 2.8. N‐ and N, S‐Heterocycles 3. Natural Raw Materials in the Flavor and Fragrance Industry 3.1. Introduction 3.2. Isolation of Natural Fragrance and Flavor Concentrates 3.2.1. Essential Oils 3.2.2. Extracts 3.3. Survey of Natural Raw Materials 4. Quality Control 5. Economic Aspects 6. Toxicology and Environmental Aspects
In creating new aroma molecules, the fragrance chemist can make use of several tools: receptor or combinatorial research as well as lead structure optimization of existing chemicals or substances from the natural pool. Sometimes, it is also possible to discover new structures via another way: the careful analysis of existing products and their production processes. In analyzing the production process of 1-oxacyclohexadecan-2-one (6), we identified at least two new oxa-bridged macrocyclic molecules. In continuation, these results inspired us to synthesize and evaluate more representatives with similar structures. In this contribution, presented at the RSC/SCI conference 'flavours & fragrances 2007' in London, September 24-26, 2007, the synthesis and olfactory properties of several new oxa-bridged macrocycles will be introduced and discussed.
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