4-Hexanolide

Description

gamma-Hexalactone has a warm, powerful, herbaceous, sweet odor and a sweet, coumarin-caramel taste. May be prepared by reduction of sorbic acid using Zn, Sn, or SnCl2 and concentrated HCL in acetic acid solution at 85°C; from ethylene oxide and sodio-malonic ester; also from propyl alcohol and methylacrylate in the presence of di-tert-butyl peroxide.

Chemical properties

4-Hexanolide is colorless liquid. Very slightly soluble in water, soluble in alcohol, Propylene glycol and oils.

Chemical properties

γ-Hexalactone has a sweet, herbaceous, warm, powerful, odor, with a sweet, coumarin-caramel taste. This compound is also described to have odor as sweet, creamy, lactonic, tobacco and coumarin-like with green coconut nuances.

Occurrence

Reported found in apple juice, apricot, orange juice, guava, raisin, papaya, peach, pineapple, berries, asparagus, peas, potato, tomato, breads, cheeses, butter, milk, chicken fat, cooked beef, cooked pork, beer, cognac, grape wines, cocoa, tea, filberts, pecans, passion fruit, Japanese plum, beans, mushroom, starfruit, mango, dried fig, prickly pear, licorice, soursop, Cape gooseberry, nectarines, quince, pawpaw and other sources.

The Uses of 4-Hexanolide

4-Hexanolide was used as curing agent for diglycidyl ether of bisphenol A with ytterbium triflate as an initiator.

The Uses of 4-Hexanolide

γ-Hexalactone may be used as an analytical standard for the determination of the analyte in wine, fruits, biological samples, meat products, and e-cigarette refill solutions by various chromatography techniques.

The Uses of 4-Hexanolide

γ-Caprolactone was used as curing agent for diglycidyl ether of bisphenol A with ytterbium triflate as an initiator.

Definition

4-Hexanolide is a gamma-lactone that is oxolan-2-one substituted by an ethyl group at position 5.

Preparation

By reduction of sorbic acid using Zn, Sn or SnCl2 and concentrated HCl in acetic acid solution at 85°C; from ethylene oxide and sodio-malonic ester; also from propyl alcohol and methylacrylate in the presence of di-tert-butyl peroxide

What are the applications of Application

4-Hexanolide finds some use in perfume compositions as a modifier for Coumarin, in Lavender and Fougere perfumes, and in many other types where Oakmoss is used as a sweetener for mossy notes. This material is more widely used in flavors, where its power and creamy sweetness is utilized for imitation Butter, Honey, Vanilla, Caramel and in fruit complexes and Tobacco flavorings.
The concentration used may vary from 0,1 ppm to 20 ppm in most of the common finished products, except in ice cream where it may be as high as 60 to 90 ppm. It performs very well with Vanillin as a synergist for the Vanilla and Cream-like flavor, an effect previously supplied by Coumarin.

Aroma threshold values

Detection: 1.6 ppm

Taste threshold values

Taste characteristics at 75 ppm: sweet, creamy, vanilla-like with green lactonic powdery nuances

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 2111, 1987 DOI: 10.1016/S0040-4039(00)96056-8

General Description

γ-Hexalactone is a volatile flavoring compound largely present in food and beverage products, fruits, vegetables, etc.

Biochem/physiol Actions

Taste at 5-10ppm