Homovanillic Acid Esters for Rapid Pungent Sensation

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Solution Overview

Problem

There is a need for less lipophilic, quickly onseting, and non-long-lasting pungent substances that create a warming taste sensation, which are either naturally occurring or formed from food components, as existing pungent substances like capsaicin and piperine have limitations due to their lipophilic nature, high potency, and potential toxicity or flavor interference.

Innovation Solution

The use of compounds of formula (I), which include specific esters of homovanillic acid, such as ethyl homovanillate, that provide a rapid and short-lasting pungent sensation, suitable for use in flavor compositions and preparations, and can be derived from natural food components like ascorbic acid and vanillyl alcohol.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Strength

If capsaicin is used to create pungent sensation, then the pungency intensity is improved, but the onset time is delayed and the sensation lasts too long

Engineering Contradiction:

Improvepungency intensityVSAvoidonset time and duration

Core Design Contradiction:

StrengthVSLoss of time

Solution Approach 1:

The patent changes the chemical parameters of the pungent substance by using homovanillic acid esters with specific molecular structures (formula I) that have different lipophilicity and metabolic properties compared to capsaicin. This allows rapid onset and short duration while maintaining pungency intensity.

Inventive Principle:

Principle #35Parameter changes

Solution Approach 2:

The invention employs pungent substances that are rapidly metabolized and eliminated from the body, creating a short-lived effect. This is achieved by selecting esters with specific properties that allow quick breakdown, providing intense but brief pungency suitable for flavor applications.

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

2Strength

If lipophilic pungent substances are used, then the pungency effect is enhanced, but the solubility in aqueous food matrices is insufficient

Engineering Contradiction:

Improvepungency effectVSAvoidsolubility

Core Design Contradiction:

StrengthVSQuantity of substance

Solution Approach 1:

The patent modifies the lipophilicity parameter of pungent substances by selecting homovanillic acid esters with optimized hydrophobic-hydrophilic balance. This allows adequate solubility in food matrices while preserving the pungent effect through appropriate molecular structure selection.

Inventive Principle:

Principle #35Parameter changes

3Ease of operation

If capsaicin is used for pungent flavor, then the sensory properties are improved, but the safety and regulatory compliance deteriorate due to genotoxicity concerns

Engineering Contradiction:

Improvesensory propertiesVSAvoidgenotoxicity and safety

Core Design Contradiction:

Ease of operationVSObject-affected harmful factors

Solution Approach 1:

The invention replaces capsaicin with homovanillic acid esters that are rapidly metabolized and excreted, minimizing exposure time and reducing potential genotoxic effects. These substitutes provide similar sensory properties without the safety concerns of capsaicin.

Inventive Principle:

Principle #27Cheap short-living objects (Disposable)

Solution Approach 2:

The patent converts the rapid metabolism characteristic into a safety benefit - the quick breakdown and elimination of homovanillic acid esters reduces cumulative exposure and potential harmful effects, while still delivering the desired pungent sensation when needed.

Inventive Principle:

Principle #22Blessing in disguise (Convert harm into benefit)

4Strength

If piperine is used to create pungent sensation, then the pungency is achieved, but the intense pepper taste interferes with other flavors

Engineering Contradiction:

ImprovepungencyVSAvoidflavor interference

Core Design Contradiction:

StrengthVSObject-generated harmful factors

Solution Approach 1:

The patent applies local quality by selecting pungent substances with specific molecular characteristics that provide trigeminal stimulation without strong aromatic properties. The homovanillic acid esters target the pungency receptors locally without introducing interfering pepper flavors.

Inventive Principle:

Principle #3Local quality

Data Source

PatentUS11535584B2Homovanillinic acid ester, in particular for creating a warm and/or pungent sensation

Publication Date: 2022.12.27 SYMRISE GMBH & CO KG

AI summary

Compounds of formula (I) and novel uses of compounds of formula (I), such as for flavour compositions. New preparations and new methods using compounds of formula (I).