Allyl heptanoate Chemical Properties

Melting point:

-66 °C

Boiling point:

210 °C

Density 

0.885 g/mL at 25 °C(lit.)

vapor pressure 

30.3Pa at 25℃

FEMA 

2031 | ALLYL HEPTANOATE

refractive index 

n20/D 1.428(lit.)

Flash point:

180 °F

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

solubility 

soluble in Methanol

form 

clear liquid

color 

A colourless liquid.

Odor

at 100.00 %. sweet pineapple fruity waxy banana fusel cognac

Odor Type

fruity

Water Solubility 

INSOLUBLE

JECFA Number

4

BRN 

8544440

InChIKey

SJWKGDGUQTWDRV-UHFFFAOYSA-N

LogP

3.97 at 20℃

CAS DataBase Reference

142-19-8(CAS DataBase Reference)

NIST Chemistry Reference

Allyl heptanoate(142-19-8)

EPA Substance Registry System

Allyl heptanoate (142-19-8)

Safety Information

Hazard Codes 

Xn

Risk Statements 

21/22-20/21/22

Safety Statements 

36/37

RIDADR 

UN 2810 6.1/PG 3

WGK Germany 

3

RTECS 

MJ1750000

TSCA 

Yes

HazardClass 

6.1

PackingGroup 

III

HS Code 

29159000

Toxicity

guinea pig,LD50,oral,444mg/kg (444mg/kg),BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY),Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964.

MSDS

• Language:English Provider:Allyl heptanoate
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Allyl heptanoate Usage And Synthesis

Chemical Properties

Allyl heptanoate is a clear colourless liquid with characteristic wine odor and a slight banana note and banana-like flavor. It has been found in wild edible mushrooms. It is used in perfume compositions for apple-like (pineapple) notes.

Occurrence

Has apparently not been reported to occur in nature.

Uses

Allyl heptanoate was one of the first to be Flavor and Extract Manufacturers Association-registered GRAS (generally recognized as safe). It can be used as part of ester complexes, primarily in fruit flavors like apple, pineapple, pear, plum, banana, fruit punch, and tropicals such as kiwi, papaya and mango. It can also play an important role in the fruity notes of aged cheeses, especially Parmesan, Asiago and grana padano.

Definition

ChEBI: Allyl heptanoate is a fatty acid ester.

Preparation

Allyl heptanoate is manufactured by direct esterification of allyl alcohol with heptanoic acid in the presence of concentrated sulfuric acid.

Taste threshold values

Taste characteristics at 10 ppm: fruity, pineapple-like with waxy tropical nuance

Toxicity evaluation

The acute oral LD₅₀ values in rats, mice and guinea-pigs were reported as 500, 630 and 444 mg/kg, respectively (Hagan, Jenner, Jones, Fitzhugh, Long, Brouwer & Webb, 1965). The acute dermal LD₅₀ value in rabbits was reported as 0.81 g/kg .(0.44-1.18 g/kg) (Moreno, 1974). Administration of 165 mg/kg by stomach tube daily for 4 days caused death in one of the six rats. Macroscopic liver lesions were observed in all animals; the livers were yellow in colour and approximately half of the hepatic tissue was necrotic(Taylor, Jenner & Jones, 1964).

General Description

Allyl heptanoate is a flavor and fragrance ingredient that may be present in karanda fruit. It has a fruity-pineapple, banana odour with mango and honey notes. It is widely used in tropical fruit composition; for perfumery applications the recommended usage level is up to 2%.

Biochem/physiol Actions

Taste at 5-10ppm

Safety Profile

Moderately toxic by ingestion and skin contact. A human skin irritant. See also ALL= COMPOUNDS and ESTERS. Combustible liquid. When heated to decomposition it emits acrid smoke and irritating fumes.

Metabolism

The hydrolysis of ester linkages in foreign compounds may be catalysed by many different esterases; most of these have a low degree of substrate specificity and they are to be found in all animals and bacteria(Parke, 1968). In the rat, allyl acetate and allyl alcohol are metabolized to 3-hydroxypropylmercapturic acid, which is excreted in the urine(Clapp, Kaye & Young, 1969). Heptanoic acid, like other odd-carbon fatty acids, is converted to glycogen with little or no formation of ketone bodies. The mechanism probably involves β-oxidation with formation of two acetic acid molecules plus one propionic acid molecule(Deuel, 1957).

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