Nerolidol

Описание

Nerolidol has a faint, floral odor similar to rose and apple. It is an unusually sweet, fresh, tenacious odor. The natural product can be dextro- or levo-rotatory, whereas the synthetic product is optically inactive; the double bond at positions 6-7 accounts for the cis- and trans-forms.

Химические свойства

Nerolidol is the sesquiterpene analog of linalool. Because of the double bond at the 6-position, it exists as (6Z)- and (6E)- isomers, each forming an enantiomeric pair, since the carbon atom in the 3-position is asymmetric. Nerolidol is a component of many essential oils. (3S,6E)-(+)-nerolidol occurs in cabreuva oil.
Synthetic nerolidol consists of a mixture of racemic (6Z)- and (6E)-nerolidol and is a colorless liquid with a long-lasting, mild floral odor. Industrial synthesis of nerolidol starts with linalool, which is converted into geranylacetone by using diketene, ethyl acetoacetate, or isopropenyl methyl ether, analogously to the synthesis of 6-methyl-5-hepten-2-one from 2-methyl- 3-buten-2-ol. Addition of acetylene and partial hydrogenation of the resultant dehydronerolidol produces a mixture of (6Z)- and (6E)-nerolidol racemates.Nerolidol is used as a base note in many delicate floral odor complexes. It is also an intermediate in the production of vitamins E and K₁.

Вхождение

Reported found in over 25 natural sources, including the essential oils of neroli, ylang-ylang, Peru balsam; in currant aroma; also reported in Dalbergia sissoo (60%, dl-), vervain, the distillation water of petitgrain bigarade, Helicrysum italicum, Myrocarpus frondosus and Myrocarpus fastigiatus (80%, d-), Tolu balsam, Acacia farnesiana, orange flower water, Paraguay petitgrain, jasmine, Melaleuca smithii and Melaleuca viridiflora. Also reported found in citrus peel oils and juices, guava, strawberry, peppermint and spearmint oil, pepper, milk powder, hop oil, beer, cognac, white wine, green tea, beans, mushroom, cardamom, rice, dill, corn oil, basil, wort, myrtle leaf, maté and mastic gum oil.

Использование

Nerolidol is one of the main component in the essential oils from fresh aerial parts of Thymus ciliatus (Lamiaceae). Also, it is a terpene that displays high potency on the contractility of cardiac muscle in guinea pig left atrium. A potential and effective treatment for malaria.

Подготовка

1) From Geranylacetone plus Acetylene, followed by reduction of the acetylenic linkage (HotTmann-laRoche process).
2) by isolation from Cabreuva oil or other essential oils.

Общее описание

Nerolidol is a naturally occurring sesquiterpene found in the essential oils.