Description
Nerolidol occurs naturally including the essential oil of neroli, ylang-ylang, and Peru balsam. It has a faint, fresh, unusually sweet, tenacious, floral odor similar to rose and apple. It can be used as a flavor ingredient in foods, such as baked goods, frozen dairy, nonalcoholic beverages, and soft candy. It is also used as fragrance in the perfumery.
References
[1] George A. Burdock, Fenaroli's Handbook of Flavor Ingredients, 6th Edition, 2010
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 has a faint, fresh, unusually sweet, tenacious, floral odor similar to rose and appe
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 K
1.
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.
Uses
anti-ulcer, insect antifeedant
Uses
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.
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.
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.
