Lactisole

Lactisole
IUPAC name Sodium 2-(4-methoxyphenoxy)propanoate
Other names Lactisole, ORP 178, Propanoic acid, 2-(4-methoxyphenoxy), sodium salt
Identifiers
CAS number	150436-68-3
PubChem	5362606
ChemSpider	4515110 Y
Jmol-3D images	Image 1
SMILES [Na+].[O-]C(=O)C(Oc1ccc(OC)cc1)C
InChI InChI=1S/C10H12O4.Na/c1-7(10(11)12)14-9-5-3-8(13-2)4-6-9;/h3-7H,1-2H3,(H,11,12);/q;+1/p-1 Y Key: SKORRGYRKQDXRS-UHFFFAOYSA-M Y InChI=1/C10H12O4.Na/c1-7(10(11)12)14-9-5-3-8(13-2)4-6-9;/h3-7H,1-2H3,(H,11,12);/q;+1/p-1 Key: SKORRGYRKQDXRS-REWHXWOFAP
Properties
Molecular formula	C10H11O4 Na
Molar mass	218.188 g/mol
Appearance	white to pale cream, crystalline solid
Melting point	190 °C
Solubility in water	Soluble in water and propylene glycol, slightly soluble in fat and miscible at room temperature in ethanol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Lactisole is a carboxylic acid salt, like gymnemic acid‎, it is a sweet-inhibitor or taste-modifier.^[1]

Chemistry

Chemically, lactisole is the sodium salt of 2-(4-methoxyphenoxy)-propionic acid. This acid has been isolated from roasted Colombian Arabica Coffee beans.^[2]

Anti-sweet properties

At concentrations of 100–150 parts per million in food, lactisole largely suppresses the ability to perceive sweet tastes, both from sugar and from artificial sweeteners such as aspartame. A 12% sucrose 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 and sodium saccharin. Research found also that it has no effect on the perception of bitterness, sourness and saltiness.^[1] 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.^[3]

As a food additive

The principal use of lactisole is in jellies, jams, 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, lactisole is designated as GRAS by the Flavor and Extract Manufacturers Association (Fema number: 3773) and approved for use in food as flavouring agent^[4] up to 150ppm. Currently, lactisole is manufactured and sold by Domino Sugar and its usage levels are between 50 and 150 ppm.^[5]

See also

• Gymnemic acid‎
• Hodulcine
• Ziziphin

References

1. ^ ^{a b} Kinghorn, A.D. and Compadre, C.M. Alernative Sweeteners: Third Edition, Revised and Expanded, Marcel Dekker ed., New York, 2001. ISBN 0-8247-0437-1
2. ^ Ivon Flament, Yvonne Bessière-Thomas, Coffee flavor chemistry, John Wiley and Sons ed., Chap: The individual constituents. p207. ISBN 0-4717-2038-0
3. ^ Lactisole Interacts with the Transmembrane Domains of Human T1R3 to Inhibit Sweet Taste. P Jiang, M Cui, B Zhao, Z Liu, LA Snyder, LMJ Benard, R Osman, RF Margolskee and M Max. J. Biol. Chem., Vol. 280, Issue 15, 15238-15246, April 15, 2005
4. ^ JECFA "Specifications for Flavourings"
5. ^ Sugar sans sweetness - lactisole. Prepared Foods, May, 1995 by Fran LaBell

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
• EAFUS: A Food Additive Database