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493:. 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
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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
513:, 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
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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
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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
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solution was perceived like a 4% sucrose solution when lactisole was added. However, it is significantly less efficient than gymnemic acid with
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525:(Fema number: 3773) and approved for use in food as flavoring agent up to 150 ppm. Currently, lactisole is manufactured and sold by
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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.
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predominating in natural sources and being primarily responsible for the sweetness-masking effect. Commercial lactisole is a
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Jiang, P.; Cui, M; Zhao, B; Liu, Z; Snyder, LA; Benard, LM; Osman, R; Margolskee, RF; Max, M (2005).
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658:"Lactisole Interacts with the Transmembrane Domains of Human T1R3 to Inhibit Sweet Taste"
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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
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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
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in food, lactisole largely suppresses the ability to perceive sweet tastes, both from
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lactisole is allowed to be used as a flavouring substance in foods, FL No. 16.041.
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Sugar sans sweetness - lactisole. Prepared Foods, May, 1995 by Fran LaBell
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Ivon
Flament; Yvonne Bessière-Thomas (2002). "The individual constituents".
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sweet protein receptor in humans, but not on its rodent counterpart.
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Lactisole; ORP 178; Propanoic acid, 2-(4-methoxyphenoxy), sodium salt
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Except where otherwise noted, data are given for materials in their
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Kinghorn, A.D.; Compadre, C.M. (2001). Marcel Dekker (ed.).
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579:(Third Edition, Revised and Expanded ed.). New York.
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and its usage levels are between 50 and 150 ppm. In the
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is the sodium salt and commonly supplied form of 2-(4-
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523:Flavor and Extract Manufacturers Association
433:Chemically, lactisole is a double ether of
599:: CS1 maint: location missing publisher (
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473:and from artificial sweeteners such as
329:white to pale cream, crystalline solid
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697:JECFA "Specifications for Flavourings"
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421:found in roasted coffee beans. Like
339:190 °C (374 °F; 463 K)
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505:The principal use of lactisole is in
247:Key: SKORRGYRKQDXRS-UHFFFAOYSA-M
49:Sodium 2-(4-methoxyphenoxy)propanoate
7:
465:At concentrations of 100–150
441:the molecule is chiral, with the S
257:Key: SKORRGYRKQDXRS-REWHXWOFAP
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746:EAFUS: A Food Additive Database
662:Journal of Biological Chemistry
631:. John Wiley and Sons. p.
365:(at 25 °C , 100 kPa).
1:
517:, lactisole is designated as
519:generally recognized as safe
321:218.188 g/mol
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771:4-Methoxyphenyl compounds
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627:Coffee flavor chemistry
437:. Since it contains an
278:.C(=O)C(Oc1ccc(OC)cc1)C
675:10.1074/jbc.M414287200
577:Alternative Sweeteners
449:of the R and S forms.
439:asymmetric carbon atom
461:Anti-sweet properties
351:Soluble in water and
776:Organic sodium salts
483:acesulfame potassium
453:Natural occurrences
346:Solubility in water
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713:2009-01-22 at the
501:As a food additive
392:Infobox references
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467:parts per million
400:Chemical compound
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200:CompTox Dashboard
104:Interactive image
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353:propylene glycol
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543:Gymnemic acid
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527:Domino Sugar
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435:hydroquinone
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417:, a natural
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63:Identifiers
55:Other names
489:and sodium
485:, sucrose,
326:Appearance
287:Properties
142:100.123.510
80:150436-68-3
755:Categories
559:References
443:enantiomer
317:Molar mass
188:ZU3D90W5GZ
115:ChemSpider
91:3D model (
70:CAS Number
46:IUPAC name
17:Lactisole
595:cite book
548:Hodulcine
491:saccharin
475:aspartame
429:Chemistry
404:Lactisole
311:Na
711:Archived
684:15668251
553:Ziziphin
537:See also
477:. A 12%
507:jellies
487:glucose
479:sucrose
411:phenoxy
408:methoxy
385:what is
383: (
168:5362606
155:PubChem
124:4515110
682:
639:
583:
495:TAS1R3
380:verify
377:
271:SMILES
40:Names
471:sugar
236:InChI
93:JSmol
680:PMID
637:ISBN
601:link
581:ISBN
511:jams
179:UNII
670:doi
666:280
633:207
205:EPA
158:CID
757::
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597:}}
593:{{
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509:,
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375:Y
309:4
307:O
303:H
299:C
207:)
203:(
95:)
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