Nerolidol

Description

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.

Chemical properties

Clear slightly yellow liquid

Chemical properties

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.

Chemical properties

Nerolidol has a faint, fresh, unusually sweet, tenacious, floral odor similar to rose and appe

Occurrence

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.

The Uses of Nerolidol

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.

The Uses of Nerolidol

anti-ulcer, insect antifeedant

What are the applications of Application

Nerolidol is a naturally occurring sesquiterpene found in the essential oils of many types of plants and flowers

Definition

ChEBI: Nerolidol is a farnesane sesquiterpenoid that is dodeca-1,6,10-triene which carries methyl groups at positions 3, 7 and 11 and a hydroxy group at position 3. It is a natural product that is present in various flowers and plants with a floral odor. Chemically, it exists in two geometric isomers, trans and cis forms. It is widely used in cosmetics (e.g. shampoos and perfumes), in non-cosmetic products (e.g. detergents and cleansers) and also as a food flavoring agent. It has a role as a flavouring agent, a cosmetic, a pheromone, a neuroprotective agent, an antifungal agent, an anti-inflammatory agent, an antihypertensive agent, an antioxidant, a volatile oil component, an insect attractant and a herbicide. It is a farnesane sesquiterpenoid, a tertiary allylic alcohol and a volatile organic compound.

Preparation

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.

Aroma threshold values

Detection: 10 ppb to 10 ppm

Taste threshold values

Taste characteristics at 25 ppm: green, floral, woody with fruity, citrus and melon nuances

General Description

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

Flammability and Explosibility

Non flammable

Synthesis

The natural product can be dextro- or levorotatory, whereas the synthetic product is optically inactive; the double bond at position 6 to 7 accounts for the cis- and trans-forms.