Nerolidol: Properties, Production process and Uses

Properties of Nerolidol

Nerolidol, also known as peruviol, 3,7,11-trimethyl-1,6,10-dodecatrien-3-ol, 3,7,11- trimethyl-1,6,10-dodecatriene-3-ol, 3,7,11-trimethyldodeca-1,6,10-trien-3-ol, 3-hydroxy- 3,7,11-trimethyl-1,6,10-dodecatriene, is a derivative of dehydronerolidol. CAS Registry Number: 7212-44-4. Molecular formula: C15H26O, molecular weight: 222.3663. The chemical structure is：

Nerolidol is a colorless to straw yellow syrupy oily liquid with a faint scent similar to rose and apple, accompanied by a very sweet, fresh, long-lasting aroma. There are (Z)- and (E)-isomers of nerolidol, which differ in the geometry on the central double bond. The physical properties of nerolidol (mixture of Z/E isomers) are listed in Table 4.7.

Production process of Nerolidol

Nerolidol was prepared by selective partial hydrogenation of dehydronerolidol in the presence of a catalyst:

An autoclave having an internal volume of 3 L was charged with 630 g of dehydronerolidol, 270 g of hexane and 0.22 g of a Lindlar catalyst (0.25% Pd supported on calcium carbonate). Hydrogenation was carried out for 4 h under hydrogen pressure of 0.5–0.8 MPa (gauge pressure) at a temperature of 25–43°C. Thereafter, the catalyst was filtered off, and the resultant filtrate was concentrated with a rotary evaporator to give 630 g of crude nerolidol. The conversion of dehydronerolidol was 95.5%, and the selectivity to nerolidol was 94.6%.

Hydrogenation of dehydronerolidol was also carried out at atmospheric or nearly atmospheric pressure in the presence of a Lindlar catalyst with 5% Pd and quinoline. Toluene was applied as the solvent instead of hexane. Under optimized conditions (catalyst dosage: 0.075% based on the mass of dehydronerolidol; ratio of solvent to dehydronerolidol: 2:1; reaction temperature: 60°C; reaction time: 5 h), the yield of nerolidol reached to 96. 2%.

Uses of Nerolidol

Nerolidol is a fragrance ingredient used in a variety of flavor formulations. It is used in food and cosmetics. Furthermore, nerolidol is applied for the manufacture of farnesyl acetone and finally production of vitamin E and K1. Nerolidol is also a key intermediate for the synthesis of squalene, which is a deep-sea fish oil health product with broad market prospects.