Nerolidol Chemical Properties

Boiling point:

145-146 °C12 mm Hg(lit.)

Density 

0.876 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.479(lit.)

Flash point:

230 °F

storage temp. 

-20°C

solubility 

DMF: miscible,DMSO: miscible,Ethanol: miscible,Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml

pka

14.40±0.29(Predicted)

Odor

at 100.00 %. floral green citrus woody waxy

Odor Type

floral

JECFA Number

1646

Merck 

13,6501

BRN 

5731231

Stability:

Light Sensitive

LogP

5.316 (est)

NIST Chemistry Reference

1,6,10-Dodecatrien-3-ol, 3,7,11-trimethyl-, (e)-(40716-66-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN1230 - class 3 - PG 2 - Methanol, solution

WGK Germany 

1

F 

10-23

Toxicity

Both the acute oral LD₅₀ in rats and the acute dermal LD₅₀ in rabbits exceeded 5 g/kg (Russell. 1973).

Nerolidol Usage And Synthesis

Description

trans-Nerolidol is a sesquiterpene that has been found in various plants, including C. sativa, and has diverse biological activities, including antimicrobial, antioxidant, anticancer, and insecticidal properties. In a disc assay, trans-nerolidol inhibits the growth of S. aureus, B. subtilis, E. coli, and S. cerevisiae with zones of inhibition measuring 10, 9, 10, and 4 mm, respectively. It reduces viability of CaCo-2 adenocarcinoma cells with an IC₅₀ value of 28.7 mg/L and reduces production of reactive oxygen species (ROS). trans-Nerolidol is insecticidal against A. aegypti larvae with a 24-hour LC₅₀ value of 9 mg/L.

Occurrence

Reported to be found in cabreuva oil, oil of neroli, balsam Peru, ylang ylang and many others (Gildemeister & Hoffman, 1959).

Uses

Nerolidol (cas# 40716-66-3) is a terpene standard found in cannabis.

Preparation

By isolation from a suitable essential oil or by chemical synthesis.

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.

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