Lactisole is the sodium salt and commonly supplied form of 2-(4-

methoxy In organic chemistry, a methoxy group is the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula . On a benzene ring, the Hammett equation classifies a methoxy substituent at the ''para'' position as ...

phenoxy In chemistry, the alkoxy group is an alkyl group which is Single bond, singularly bonded to oxygen; thus . The range of alkoxy groups is vast, the simplest being methoxy (). An ethoxy group () is found in the organic compound ethyl phenyl ethe ...

)

propionic acid Propionic acid (, from the Greek words πρῶτος : ''prōtos'', meaning "first", and πίων : ''píōn'', meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula CH3CH2CO2H. It is a liq ...

, a natural

carboxylic acid In organic chemistry, a carboxylic acid is an organic acid that contains a carboxyl group () attached to an R-group. The general formula of a carboxylic acid is or , with R referring to the alkyl, alkenyl, aryl, or other group. Carboxylic ...

found in roasted coffee beans. Like

gymnemic acid Gymnemic acids are a class of chemical compounds isolated from the leaves of ''Gymnema sylvestre'' (Asclepiadaceae). They are anti-sweet compounds, or sweetness inhibitors. After chewing the leaves, solutions sweetened with sugar taste like water. ...

, it has the property of masking sweet flavors and is used for this purpose in the food industry.

Chemistry

Chemically, lactisole is a double ether of

hydroquinone Hydroquinone, also known as benzene-1,4-diol or quinol, is an aromatic organic compound that is a type of phenol, a derivative of benzene, having the chemical formula C6H4(OH)2. It has two hydroxyl groups bonded to a benzene ring in a ''para'' ...

. Since it contains an asymmetric carbon atom the molecule is chiral, with the S

enantiomer In chemistry, an enantiomer ( /ɪˈnænti.əmər, ɛ-, -oʊ-/ ''ih-NAN-tee-ə-mər''; from Ancient Greek ἐνάντιος ''(enántios)'' 'opposite', and μέρος ''(méros)'' 'part') – also called optical isomer, antipode, or optical ant ...

predominating in natural sources and being primarily responsible for the sweetness-masking effect. Commercial lactisole is a

racemic mixture In chemistry, a racemic mixture, or racemate (), is one that has equal amounts of left- and right-handed enantiomers of a chiral molecule or salt. Racemic mixtures are rare in nature, but many compounds are produced industrially as racemates. ...

of the R and S forms.T. Nakagita et al "Structural insights into the differences among lactisole derivatives in inhibitory mechanisms against the human sweet taste receptor" PLoS One. 2019; 14(3): e0213552

Natural occurrences

The parent acid of lactisole was discovered in 1989 in roasted Colombian arabica coffee beans in a concentration of 0.5 to 1.2 ppm.

Anti-sweet properties

At concentrations of 100–150

parts per million In science and engineering, the parts-per notation is a set of pseudo-units to describe small values of miscellaneous dimensionless quantities, e.g. mole fraction or mass fraction. Since these fractions are quantity-per-quantity measures, they ...

in food, lactisole largely suppresses the ability to perceive sweet tastes, both from

sugar Sugar is the generic name for sweet-tasting, soluble carbohydrates, many of which are used in food. Simple sugars, also called monosaccharides, include glucose, fructose, and galactose. Compound sugars, also called disaccharides or double ...

and from artificial sweeteners such as

aspartame Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with the trade names ...

. A 12%

sucrose Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula . For human consumption, sucrose is extracted and refined ...

solution was perceived like a 4% sucrose solution when lactisole was added. However, it is significantly less efficient than gymnemic acid with acesulfame potassium, sucrose,

glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using ...

and sodium

saccharin Saccharin (''aka'' saccharine, Sodium sacchari) is an artificial sweetener with effectively no nutritional value. It is about 550 times as sweet as sucrose but has a bitter or metallic aftertaste, especially at high concentrations. Saccharin is u ...

. Research found also that it has no effect on the perception of bitterness, sourness and saltiness. According to a recent study, lactisole acts on a sweet taste receptor heteromer of the TAS1R3 sweet protein receptor in humans, but not on its rodent counterpart.

As a food additive

The principal use of lactisole is in jellies,

jam Jam is a type of fruit preserve. Jam or Jammed may also refer to: Other common meanings * A firearm malfunction * Block signals ** Radio jamming ** Radar jamming and deception ** Mobile phone jammer ** Echolocation jamming Arts and entertai ...

s, and similar preserved fruit products containing large amounts of sugar. In these products, by suppressing sugar's sweetness, it allows fruit flavors to come through. In the

United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country primarily located in North America. It consists of 50 states, a federal district, five major unincorporated territorie ...

, lactisole is designated as generally recognized as safe (GRAS) by the

Flavor and Extract Manufacturers Association The Flavor and Extract Manufacturers Association (FEMA) is a food industry trade group based in the United States. FEMA was founded in 1909 by several flavor firms in response to the passage of the Pure Food and Drug Act of 1906. Founding members ...

(Fema number: 3773) and approved for use in food as flavoring agentJECFA "Specifications for Flavourings"
/ref> up to 150 ppm. Currently, lactisole is manufactured and sold by

Domino Sugar Domino Foods, Inc. (also known as DFI and formerly known as W. & F.C. Havemeyer Company, Havemeyer, Townsend & Co. Refinery, and Domino Sugar) is a privately held sugar marketing and sales company based in Yonkers, New York, United States, that ...

and its usage levels are between 50 and 150 ppm.Sugar sans sweetness - lactisole. Prepared Foods, May, 1995 by Fran LaBell
In the

European Union The European Union (EU) is a supranational political and economic union of member states that are located primarily in Europe. The union has a total area of and an estimated total population of about 447million. The EU has often been des ...

lactisole is allowed to be used as a flavouring substance in foods, FL No. 16.041. 2002/113/EC: Commission Decision of 23 January 2002 amending Commission Decision 1999/217/EC as regards the register of flavouring substances used in or on foodstuffs
/ref>

References

{{Reflist

External links

List of substances scheduled for evaluation or re-evaluation at the fifty-ninth meetingof the Joint FAO/WHO Expert Committee on Food Additives (JECFA). 2002

Taste modifiers Food additives Phenol ethers Carboxylate esters Organic sodium salts