Basic information Chemical Properties Content Analysis Toxicity Use limits Uses Production method Hazards & Safety Information Safety Supplier Related
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Allyl hexanoate

Basic information Chemical Properties Content Analysis Toxicity Use limits Uses Production method Hazards & Safety Information Safety Supplier Related

Allyl hexanoate Basic information

Product Name:
Allyl hexanoate
Synonyms:
  • Propylene caproate
  • ALLYL CAPROATE
  • ALLYL HEXANOATE
  • ALLYL N-HEXANOATE
  • CAPROIC ACID ALLYL ESTER
  • FEMA 2032
  • HEXANOIC ACID ALLYL ESTER
  • ALLYL HEXANOATE 98+% NATURAL FCC
CAS:
123-68-2
MF:
C9H16O2
MW:
156.22
EINECS:
204-642-4
Product Categories:
  • lactone flavors
Mol File:
123-68-2.mol
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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.)
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
form 
neat
Water Solubility 
PRACTICALLY INSOLUBLE
JECFA Number
3
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)
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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

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Allyl hexanoate Usage And Synthesis

Chemical Properties

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

Content Analysis

Accurately weigh 1g of samples and analyze its content according to ester determination (OT-18). The equivalent factor (e) in the calculation is taken as 78.12.

Toxicity

LD50 218 mg/kg (rat, oral).
ADI 0~0.13 mg/kg (FAO/WHO, 1994).

Use limits

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

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. GB 2760--1996 provides that allyl hexanoate is the food spices temporally allowed to use, which is mainly used in the preparation of pineapple, apple and other fruit spices.
4. 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.
5. 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.

Production method

Production method 1
Hexanoic acid and allyl alcohol directly perform esterification in catalysis of sulfuric acid, and then the prepared esters are neutralized, washed and distillated to obtain the finished products.
Production method 2
(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, the finished products were obtained by further filtration and vacuum distillation.
Production method 3
Secondary octanol were oxidized by nitric acid to generate various organic acids based on hexanoic acid and heptanoic acid. The above acids mixture were then fractionated to obtain n-caproic acid, which then performed esterification with allyl alcohol in the presence of concentrated sulfuric acid. The reaction products were then dehydrated with benzene, washed and fractionated to obtain the finished allyl hexanoate.
Production method 4
(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 with 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 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, the finished products 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

CLEAR COLOURLESS LIQUID

Chemical Properties

2-Propenyl Hexanoate has been shown to occur in pineapple. It has a typical pineapple odor and is used in, for example, pineapple flavors.

Chemical Properties

A colorless liquid with fruity sweet, pineapple-like taste and fruit-like aroma (pineapple)

Occurrence

Reported found in baked potato, mushroom and pineapple.

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.

Preparation

By esterification of n-caproic acid with allyl alcohol in the presence of concentrated H2SO4 or of naphthalene-β-sulfonic acid in benzene under a nitrogen blanket

Taste threshold values

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

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.

Allyl hexanoateSupplier

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