Allyl hexanoate Chemical Properties

Melting point:

-57.45°C (estimate)

Boiling point:

75-76 °C/15 mmHg (lit.)

Density 

0.887 g/mL at 25 °C (lit.)

vapor pressure 

2.69hPa at 25℃

FEMA 

2032 | ALLYL HEXANOATE

refractive index 

n20/D 1.424(lit.)

Flash point:

151 °F

storage temp. 

Sealed in dry,Room Temperature

solubility 

0.06g/l

color 

Colorless to Almost colorless

Odor

at 10.00 % in dipropylene glycol. sweet fruity pineapple tropical ethereal rum arrack fatty cognac

Odor Type

fruity

Water Solubility 

PRACTICALLY INSOLUBLE

JECFA Number

3

LogP

3.191 at 20℃

CAS DataBase Reference

123-68-2(CAS DataBase Reference)

NIST Chemistry Reference

Hexanoic acid, 2-propenyl ester(123-68-2)

EPA Substance Registry System

Allyl hexanoate (123-68-2)

Safety Information

Hazard Codes 

T,N

Risk Statements 

22-24-51/53-R51/53-R24-R22

Safety Statements 

36/37-45-61-S61-S45-S36/37

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

2

RTECS 

MO6125000

HazardClass 

6.1(b)

PackingGroup 

III

HS Code 

29159080

Toxicity

The acute oral LD₅₀ in rats was 218 mg/kg and in guinea-pigs 280 mg/kg . The acute dermal LD₅₀ for sample no. 71-20 was reported as 0-3ml/kg in the rabbit

MSDS

• Language:English Provider:2-Propenyl n-hexanoate
• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

Allyl hexanoate Usage And Synthesis

Chemical Properties

Colorless to pale yellow liquid; pineapple aroma; Soluble in organic solvents; insoluble in water.

Uses

1. Allyl hexanoate is Used for the preparation of pineapple and other fruit flavors.
2. China provides that allyl hexanoate is the spices temporally allowed to use, which is commonly used in the modulation of food spices and tobacco spices with the flavor of strawberry, apricot, peach, sweet orange, pineapple, apple and other fruit. The use amount of allyl hexanoate is according to the normal production needs, such as 210 mg/kg in chewing gum, 32mg/kg in confectionery, 25 mg/kg in baked goods and 11 mg/kg in cold drinks.
3. Allyl caproate finds use in perfumes as a part of fruity top notes in combination with green mossy notes. it may form a characteristic part of the fragrance. It also tends to round off the Aldehyde notes in combination with styrallyl esters. it has found extensive use in apple, apricot, orange, peach, pineapple, rum, strawberry, tutti-frutti, etc.
4. Widely used in the preparation of food flavors, spices, tobacco flavors and pineapple and other fruit flavors, and also used as an organic synthesis of intermediates.

Use limits

FEMA (mg/kg): soft drinks 7.0; cold drinks 11.0; candy 32; baked food 25; pudding class 22;

Production method

synthesis of allyl hexanoate
(1) solid acid catalytic method: Add 23.2 g (0.4 mol) of propenol, 23.2 g (0.2 mol) of hexanoic acid, 0.1 g of hydroquinone, 3.0 g of solid super TiO2/SO4-2 and 30 mL of toluene into a 150 mL flask. Heat for reflux for 1.5h and the generated water were taken out by the azeotropic agent toluene. The reaction solution was cooled and filtered, and the solid acid could be repeatedly used after being dried. Add 0.1g of cuprous chloride in the filtrate, and then distillate them to collect the fraction of 186-188 ° C. The obtained finished products was 27.1g with a yield of 86.9%, and the refractive index n20d was 1.4241.
(2) sulfuric acid catalytic method: Firstly, hexanoic acid and allyl alcohol performed esterification in catalysis of sulfuric acid. After the end of the reaction, the above esters were washed with water and then were neutralized with 15% Na2CO3 solution and washed with water to neutral. Add anhydrous sodium carbonate or anhydrous calcium chloride for dehydration. Finally, Allyl hexanoate were obtained by further filtration and vacuum distillation.

Hazards & Safety Information

Category  Toxic substances
Toxicity classification high toxicity
Acute toxicity peritoneal-rat LD50: 218 mg/kg; Oral-guinea pig LD50: 280 mg/kg
Stimulation Data Skin-human 20 mg/48 h mild
Flammability Hazardous characteristics
Flammable; Combustion produces irritating fumes
Storage and transportation characteristics
Stored in the low-temperature, well-ventilated and dry warehouse; stored separately with food raw materials
Fire extinguishing agent
dry powder, foam, sand, carbon dioxide, mist water

Chemical Properties

Allyl hexanoate is a colorless to slightly yellow transparent liquid with fruity sweet, pineapple-like taste and fruit-like aroma (pineapple). It has been shown to occur in pineapple. It has a typical pineapple odor and is used in, for example, pineapple flavors.

Occurrence

Allyl hexanoate has also been reported to occur naturally in baked potato, mushroom and pineapples.

Uses

Allyl Hexanoate is a liquid flavoring agent with a strong pineapple odor and pale yellow color. it is practically insoluble in propylene glycol and miscible with alcohol, most fixed oils, and mineral oil. it is obtained by chemical synthesis. it can be used alone or in com- bination with other flavoring substances or adjuvants. it is also termed allyl caproate.

Definition

ChEBI: 2-Propenyl hexanoate is a fatty acid ester.

Preparation

Allyl hexanoate is directly esterified by hexanoic acid and allyl alcohol under the catalysis of sulfuric acid, and then neutralized, washed with water and rectified to obtain the finished product.

Taste threshold values

Taste characteristics at 10 ppm: sweet, fresh, juicy, pineapple and fruity

General Description

Allyl hexanoate is a volatile flavoring compound with a pineapple flavor. It is naturally found in pineapple, baked potatoes and mushrooms. Allyl hexanoate is used as a flavoring agent in chewing gum, candies and baked goods.

Safety Profile

Poison by ingestion and skin contact. Mutation data reported. An irritant to human skin. When heated to decomposition it emits acrid smoke and irritating fumes. See also ALLYL COMPOUNDS and ESTERS

Metabolism

Clapp, Kaye & Young (1969) have reported on the metabolism of allyl compounds in the rat. These compounds react with reduced glutathione in the liver and the resultant product, after hydrolysis and N-acetylation gives rise to the mercapturic acid, which is readily excreted in the urine.

Solubility in organics

Almost insoluble in water, miscible withalcohol, essential oils and perfume and flavorchemicals.

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