Nerolidol Property

Melting point:

-75 °C

Boiling point:

114 °C/1 mmHg (lit.)

Density 

0.875 g/mL at 25 °C (lit.)

vapor pressure 

<1 hPa (20 °C)

FEMA 

2772 | NEROLIDOL (ISOMER UNSPECIFIED)

refractive index 

n20/D 1.479(lit.)

Flash point:

230 °F

storage temp. 

Store below +30°C.

solubility 

0.014g/l, Very slightly soluble in water, soluble in alcohol and oils.

form 

Liquid

pka

14.44±0.29(Predicted)

color 

Clear slightly yellow

Specific Gravity

0.88

Odor

at 100.00 %. floral green waxy citrus woody

Odor Type

floral

explosive limit

0.7-4.5%(V)

Water Solubility 

immiscible

Merck 

14,6476

JECFA Number

1646

BRN 

1724135

LogP

4.5 at 24℃

CAS DataBase Reference

7212-44-4(CAS DataBase Reference)

NIST Chemistry Reference

1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-(7212-44-4)

EPA Substance Registry System

Nerolidol (7212-44-4)

Safety

Hazard Codes 

Xi,N

Risk Statements 

36/37/38-50/53

Safety Statements 

26-36-61-60

RIDADR 

UN 3082 9 / PGIII

WGK Germany 

2

RTECS 

JR4977000

F 

10-23

Autoignition Temperature

230 °C

TSCA 

Yes

HS Code 

29052290

Toxicity

LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 5000 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Nerolidol Chemical Properties,Usage,Production

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

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

Chemical Properties

Clear slightly yellow liquid

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

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.

Uses

anti-ulcer, insect antifeedant

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.