Terpinen-4-ol

Chemical properties

colourless or pale yellow liquid

Chemical properties

1-Terpinen-4-ol occurs as (+)-, (?)-, and racemic 1-terpinen-4-ol in many essential oils, for example, from Pinus and Eucalyptus species, and in lavender oil. It is a colorless liquid with a spicy, nutmeg-like, woody–earthy, and also lilac-like odor.
1-Terpinen-4-ol is a by-product in the synthesis of terpineol fromterpin hydrate and occurs in commercial terpineol. Pure 1-terpinen-4-ol can be prepared from terpinolene by photosensitized oxidation, reduction of the resulting 1-methyl-4- isopropenyl-1-cyclohexene-4-hydroperoxide, and selective hydrogenation of the corresponding alcohol.
It is used, for example, in artificial geranium and pepper oils and in perfumery for creating herbaceous and lavender notes.

Occurrence

4-Carvomenthenol (dextro) has been reported present in the oil of Cupressus macrocarpa lavender, Spanish origanum, Ledum palustre, Eucalyptus australiana var. A., Thuja occidentalis, etc. The l-form is present in the oil of Eucalyptus dives and in some other essences such as Xanthoxylum rhetsa, together with the racemic form. The racemic form is found in camphor oil. Reported found in fresh apple, apricots, orange juice, peel oils of orange, lemon, grapefruit, tangerines, anise, cinnamon, ginger and nutmeg.

The Uses of Terpinen-4-ol

Shows antioxidant effects. Antiseptic.

The Uses of Terpinen-4-ol

Reference Standard in the analysis of herbal medicinal products

What are the applications of Application

rac Terpinen-4-ol is an antioxidant

Definition

ChEBI: A terpineol that is 1-menthene carrying a hydroxy substituent at position 4.

Taste threshold values

Taste characteristics at 30 ppm: sweet, citrus green with a tropical fruity character.

General Description

Produced and qualified by HWI pharma services GmbH.
Exact content by quantitative NMR can be found on the certificate.

Flammability and Explosibility

Not classified

Biochem/physiol Actions

Taste at 30 ppm

Anticancer Research

Also this molecule exhibits antitumor effects by apoptotic mechanism. Studies weredone in mice bearing A549 tumor xenografts (Quintans et al. 2013; Kiyan et al.2014).

Synthesis

One of several terpinenol isomers, depending on the position of the double bond and that of the hydroxyl group, this terpene, whose structure has been defined by Wallach, can be isolated by fractional distillation. It exists in nature as the dextro, levo and racemic isomer; the synthetic product is always optically inactive. The 1-terpineneol or 1-meththyl-4-isopropyl-3-cyclohexen-1-ol has been prepared by Wallach (Burdock, 1997).