106-25-2

Identification test

Determination of total alcohol (OT-5). The amount of sample taken is 1.2g; the equivalent factor (e) in the calculation is 77.13.

Preparation

1. Oil of petitgrain is used as raw material; the first step is eliminating linalool and terpenes through fractionation; through saponification the fraction containing primary alcohol will be made into phthalate esters; and then going through purification and alkali saponification, geraniol (60 %) and nerol (40%) mixture is derived; removing geraniol with lead chloride, undergoing the residue vacuum distillation or steam distillation, the product was derived. 2. Let the geraniol and hydroiodic acid reacted in the neutral solution. Removing excess hydrogen iodide with alkali, the nerol mixed with geraniol can be derived, and then separate the mixture using the above method. 3. Heat the mixture of the same amount of camphor and acetic anhydride to boiling in the presence of sodium acetate. The mixture of geraniol and neryl alcohol can be derived through saponified esterification, and then separate the mixture by the former method. 4. Reducing citral in the isopropanol solution containing isopropanol aluminium also can obtain the mixture of geraniol and nerol, and nerol is derived through re-separation.

Toxicity

GRAS (FEMA). LD504500 mg/kg (rat, oral). maximum level?? ?FEMA (mg/kg): soft drink 1.4; cold drink 3.9; candy 16; baked food 19; pudding 1.0 to 1.3; utilization limitation (FDA $ 172. 515, 2000).

Synthesis Reference(s)

Tetrahedron, 40, p. 641, 1984 DOI: 10.1016/S0040-4020(01)91092-0Tetrahedron Letters, 33, p. 5417, 1992 DOI: 10.1016/S0040-4039(00)79109-XSynthesis, p. 328, 1988 DOI: 10.1055/s-1988-27559

Safety Profile

Moderately toxic by intramuscular route. Mildly toxic by ingestion. A skin irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

Chemical properties

Colorless oily liquid It bears a sweet smell similar to the fresh rose, better than geraniol, and with hints of lemon flavor. The boiling point is 227 ℃; flash point is 92 ℃; optical rotation is [α] D ± 0 °. Miscible in ethanol, chloroform and ether; nearly insoluble in water. It is the isomer of geraniol (trans; geraniol is cis). Natural lanolin and its esters are found in orange leaf oil, rose oil, lavender oil, Sri Lanka citronella oil, bitter orange blossom oil and bergamot, lemon, white lemon, grapefruit, sweet orange and so on.

Definition

ChEBI: The (2Z)-stereoisomer of 3,7-dimethylocta-2,6-dien-1-ol. It has been isolated from the essential oils from plants like lemon grass.

Aroma threshold values

Detection: 680 ppb to 2.2 ppm; aroma characteristics at 2%: rosy, slightly citrus, terpy and floral, reminiscent of linalool oxide with aldehydic waxy and fruity nuances

Taste threshold values

Taste characteristics at 10 ppm in 5% sugar and 0.1% CA: rosy with citrus nuances, fruity pear with floral citronellal notes

General Description

The antifungal efficacy of nerol (cis-3,7-Dimethyl-2,6-octadien-1-ol), against Aspergillus flavus, was studied.