Pineapple flavor and Allyl caproate

My favorite unit in O-Chem(Organic Chemistry) was when the professor brought in a small bottle of Allyl caproate (aka Allyl hexanoate FEMA #2032) for the class to evaluate. It was my first exposure to a flavor aromatic.

He passed around the bottle and asked us carefully smell the bottle and tell the class what we thought. I was intrigued, it smelled like pineapple. From that moment on, I was hooked on O-Chem.

Pineapple

The unit’s focus was probably naming or was focused on esters. Allyl caproate is an ester. Esters are often times described as fruity.  Allyl describes the group of atoms attached to the ester group.

625px-Ester-general

Ester group

 

Allyl

Allyl group

 

http://www.sigmaaldrich.com/catalog/product/aldrich/w203203?lang=en&region=US

Allyl hexanoate (Sigma-aldrich)

 

 

Allyl caproate is fruity and smells like pineapple, but also has a plastic or waxy character. In nature, it has been identified as a component of pineapple, baked potato and mushroom. It characterizes pineapple flavor but it must be blended with other aromatics to become a good pineapple flavor.

Other aromatics I would use in pineapple flavor include fruity, sweet esters such as Allyl cyclohexyl propionate, iso-Amyl acetate, Amyl butyrate, Ethyl acetate, and Ethyl butyrate. Orange essential oil adds subtle juiciness that adds “pulpiness” to a pineapple flavor.

Adding a bit of a ripe sulfur note makes a pineapple flavor seem real. Ethyl 3-methyl the propionate (identified in nature as a component of pineapple, melon, parmesan cheese, whiskey, wine and passionfruit) is an excellent choice of an aromatic which can add a sweet real ripe character to a pineapple flavor.

Pineapple flavor can be found in confections : See’s chocolate covered pineapple truffle or Jelly Belly crushed pineapple. Pineapple is also a very needed flavor accent in Hawaiian punch flavor, piña-colada or Teriyaki sauce. Often times in food products, pineapple flavor is a top note for pineapple concentrate. A tiny amount of added flavor assures that the product still tastes good, even if it’s been in your pantry a few weeks or months.

My favorite pineapple flavored food product: Chobani Pineapple yogurt.  What’s yours?

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  1. Allyl caproate is employed principally in the formulation of pineapple flavors but it canas als be used for peach and apricot essences and for apple blossom, peach blossom, and wisteria perfume compositions. Allyl caproate is an ingredient of some lipstick perfumes. Adds a sweet juicy note to citrus flavors.