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Chemistry of Essential Oils
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
Various other natural extracts are used as feedstocks for the production of terpenoids as shown in Figure 6.35. Two of the most significant ones are clary sage and the citrus oils (obtained as by-products of the fruit juice industry). After distillation of the oil from clary sage, sclareol (203) is extracted from the residue, and this serves as a starting material for naphthofuran (204), known under trade names such as Ambrofix, Ambrox, and Ambroxan. The conversion is shown in Figure 6.35. Initially, sclareol is oxidized to sclareolide (205). This was once effected using oxidants such as permanganate and dichromate, but nowadays, the largest commercial process uses a biotechnological oxidation. Sclareolide is then reduced using lithium aluminum hydride, borane, or similar reagents and the resulting diol is cyclized to the naphthofuran. d-Limonene (73) and valencene (206) are both extracted from citrus oils. Reaction of d-limonene with nitrosyl chloride gives an adduct that is rearranged to the oxime of l-carvone, and subsequent hydrolysis produces the free ketone (105). Selective oxidation of valencene gives nootkatone (135).
Catalog of Herbs
Published in James A. Duke, Handbook of Medicinal Herbs, 2018
Dried leaves are used occasionally for flavoring in cookery. Leaves and flowers yield an essential oil, oil of clary sage, used in perfumery and in flavorings, combining a delicate fragrance with a powerful odor. Oil and absolute are used in colognes, creams, detergents, lotion, perfume, soap, and tobacco, with leaves up to 0.8% in perfumes. In Germany it is added to wines to give them a musky bouquet (e.g., muscatel). Either flowers alone, or the whole plant with the woody stalks removed, are used to extract the oil. High grade oil has a typical odor, reminescent of ambergris, which blends well with lavender, bergamot, or jasmine. The oil is used in beverages, baked goods, candy, gelatins, liqueurs, puddings, relishes, and spices, with highest use of around 155 ppm for the oil in alcoholic beverages.29 After the essential oil has been distilled, the residue is used as a source of sclareol, used like its derivative sclareolide for flavoring tobacco. Sclareolide is used in producing an ambergris substitute.29
Sclareol attenuates the development of atopic dermatitis induced by 2,4-dinitrochlorobenzene in mice
Published in Immunopharmacology and Immunotoxicology, 2019
Po-Chang Wu, Wen-Ho Chuo, Shih-Chao Lin, Caitlin W. Lehman, Christopher Z. Lien, Chieh-Shan Wu, Chi-Chien Lin
Sclareol was purchased directly from Sigma-Aldrich Co. (St. Louis, MO) and dissolved in the corn oil/DMSO vehicles (v/v, 95/5) prior to use. Two sclareol-treated groups (n= 6 for each group) were given 5 and 10 mg/kg of sclareol via intraperitoneal injection every other day from day 7 to day 31 over the animal experiment, for a total of 12 treatments. Two control cohorts were incorporated in this study: normal control, sensitized only with mixture of acetone and olive oil without sclareol treatment, and vehicle control, defined as DNCB-sensitized and injected with oil/DMSO vehicles instead of sclareol.