Allyl hexanoate and heptanoate

How to reproduce the Pineapple flavor

Allyl hexanoate and heptanoate

How to reproduce the Pineapple flavor

Allyl hexanoate (allyl caproate, 2-propenyl hexanoate) is a colourless to pale yellow liquid flavour with a strong pineapple aroma. It is used not only for food applications (spices, tobacco flavours, pineapple and other fruit flavours), but it is also an ingredient of some lipstick perfumes and it can be used to add that juicy note to citrus flavours.

The most common production method is esterification of hexanoic acid and allyl alcohol in catalysis of sulfuric acid; the obtained esters are then neutralized, washed and distilled to obtain the finished compound.

Allyl heptanoate (2-Propenyl Heptanoate) 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%.

It is manufactured by direct esterification of allyl alcohol with heptanoic acid.

The pineapple aroma

These two raw materials can be used in the formulation of the Pineapple aroma. By tasting and smelling the pineapple fruit, the notes of the pineapple flavour have been identified. Therefore, the natural taste of the fruit can be imitated by mixing natural or synthetic raw materials with the corresponding notes.

Even if flavour recipes are trade secrets, a typical pineapple flavour contains the following ingredients:

Flavour ingredient

Wt %

ECSA’S MP code

ALLYL HEXANOATE

10.83

MP 030183 

ALLYL HEPTANOATE

10.69

MP 027087 

ALLYL CYCLOHEXYL PROPIONATE

4.72

/

1% ETHYL 3-METHYLTHIOPROPIONATE

0.15

/

1% METHYL 3-METHYLTHIOPROPIONATE

0.17

/

ETHYL BUTYRATE

0.29

MP 010636

ISOAMYL ACETATE

0.31

MP 001358 

ISOAMYL BUTYRATE

0.79

/

ETHYL ACETATE

0.14

MP 010033

SWEET ORANGE OIL

8.7

MP 030437 

LEMON OIL

0.75

MP 027787 

CITRAL

0.02

MP 031380

ALDEHYDE C14

0.63

MP 022459

ALDEHYDE C18

0.64

MP 022467 

VANILLIN

1.57

MP 031617 

MALTOL

1.82

MP 031765 

10% FURANEOL

0.26

MP 027049 

ETHYL HEXANOATE

0.13

MP 028374 

ETHYL HEPTANOATE

0.67

MP 000936 

γ-VALEROLACTONE

0.23

/

γ-HEXALACTONE

0.21

/

γ-HEPTALACTONE

0.01

/

ACETIC ACID

0.01

MP 010892 

1% METHIONAL

0.01

/

PINEAPPLE BASE

2.5

/

ETHANOL

40.7

Available only for Swiss customers

PROPYLENE GLYCOL

13.05

MP 021816

TOTAL 

100

 

Source: Food Science and Technology, “A pineapple flavor imitation by the note method”, Guangyong ZHU1, Genfa YU, ISSN 1678-457X (Online), Oct-Dec 2020

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