142-19-8 Usage
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).
Check Digit Verification of cas no
The CAS Registry Mumber 142-19-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,4 and 2 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 142-19:
(5*1)+(4*4)+(3*2)+(2*1)+(1*9)=38
38 % 10 = 8
So 142-19-8 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O2/c1-3-5-6-7-8-10(11)12-9-4-2/h4H,2-3,5-9H2,1H3
142-19-8Relevant articles and documents
Practical preparation of esters and thioacetates from alkyl halides and carboxylates or thioacetate catalyzed by PEG400 without solvent
Cao, Yu-Qing,Wu, Guo-Qiang,Li, Ya-Bin,Dai, Zhi,Chen, Bao-Hua
, p. 3353 - 3358 (2007/10/03)
Carboxylic esters and thioacetates were conveniently prepared in good to excellent yields under mild conditions by the reaction of alkyl halides with sodium carboxylates or sodium thioacetate catalyzed by PEG400 in the absence of solvents. Copyright Taylor & Francis Group, LLC.
Odor-structure relationships using fluorine as a probe
Michel, Dominique,Schlosser, Manfred
, p. 4253 - 4260 (2007/10/03)
Eight ethers, nine esters and one ketone were submitted to a systematic structural variation by replacing a hydrogen atom in the vicinity of the oxofunction by fluorine and methyl. As long as steric factors dominate, a fluorine substituent alters the olfactory properties of the parent compound much less than a methyl substituent does. However, if it occupies a position adjacent to a carbonyl group, the halogen may more profoundly affect the odor perception, presumably as a consequence of conformational changes. (C) 2000 Elsevier Science Ltd.
