4-Hexanolide Property

Melting point:

-18°C

Boiling point:

219 °C(lit.)

Density 

1.023 g/mL at 25 °C(lit.)

vapor pressure 

2.4hPa at 20℃

FEMA 

2556 | GAMMA-HEXALACTONE

refractive index 

n20/D 1.439(lit.)

Flash point:

209 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

Specific Gravity

1.023

color 

Colorless to Almost colorless

Odor

at 10.00 % in dipropylene glycol. herbal coconut sweet coumarin tobacco

Odor Type

tonka

Water Solubility 

77g/L at 20℃

JECFA Number

223

BRN 

107260

LogP

0.3 at 20℃

CAS DataBase Reference

695-06-7(CAS DataBase Reference)

NIST Chemistry Reference

2(3H)-Furanone, 5-ethyldihydro-(695-06-7)

EPA Substance Registry System

2(3H)-Furanone, 5-ethyldihydro- (695-06-7)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38-36

Safety Statements 

26-36

WGK Germany 

2

RTECS 

LU4220000

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29322090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

Precautionary statements

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-Hexanolide Chemical Properties,Usage,Production

Aroma

Warm, powerfully herbaceous, sweet "Tobacco-like", coumannic type odor. Sweet, powerful, warm-herbaceous, Coumarin-Caramel taste.

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

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.

Chemical Properties

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

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.

Uses

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.

Uses

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

Uses

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

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

Definition

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

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