Sucralose

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Sucralose [1]
Haworth projection of sucralose.svg
Sucralose-from-xtal-3D-bs-17.png
Names
IUPAC name
1,6-Dichloro-1,6-dideoxy-β-D-fructofuranosyl 4-chloro-4-deoxy-α-D-galactopyranoside
Systematic IUPAC name
(2R,3R,4R,5R,6R)-2-{[(2R,3S,4S,5S)-2,5-Bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-chloro-6-(hydroxymethyl)oxane-3,4-diol
Other names
  • 1′,4,6′-Trichlorogalactosucrose
  • Trichlorosucrose
  • E955
  • 4,1′,6′-Trichloro-4,1′,6′-trideoxygalactosucrose
  • TGS
  • Splenda [2]
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.054.484 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 259-952-2
E number E955 (glazing agents, ...)
KEGG
PubChem CID
UNII
  • InChI=1S/C12H19Cl3O8/c13-1-4-7(17)10(20)12(3-14,22-4)23-11-9(19)8(18)6(15)5(2-16)21-11/h4-11,16-20H,1-3H2/t4-,5-,6+,7-,8+,9-,10+,11-,12+/m1/s1 Yes check.svgY
    Key: BAQAVOSOZGMPRM-QBMZZYIRSA-N Yes check.svgY
  • InChI=1/C12H19Cl3O8/c13-1-4-7(17)10(20)12(3-14,22-4)23-11-9(19)8(18)6(15)5(2-16)21-11/h4-11,16-20H,1-3H2/t4-,5-,6+,7-,8+,9-,10+,11-,12+/m1/s1
    Key: BAQAVOSOZGMPRM-QBMZZYIRBF
  • Cl[C@H]2[C@H](O[C@H](O[C@@]1(O[C@@H]([C@@H](O)[C@@H]1O)CCl)CCl)[C@H](O)[C@H]2O)CO
Properties
C12H19Cl3O8
Molar mass 397.63 g·mol−1
AppearanceOff-white to white powder
Odor Odorless
Density 1.69 g/cm3
Melting point 125 °C (257 °F; 398 K)
283 g/L (20 °C)
Acidity (pKa)12.52±0.70
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Sucralose is an artificial sweetener and sugar substitute. As the majority of ingested sucralose is not metabolized by the body, it adds minimal calories (3 per gram). [3] In the European Union, it is also known under the E number E955. It is produced by chlorination of sucrose, selectively replacing three of the hydroxy groups —in the C1 and C6 positions of the fructose portion and the C4 position of the glucose portion—to give a 1,6-dichloro-1,6-dideoxyfructose–4-chloro-4-deoxygalactose disaccharide. Sucralose is about 600 times sweeter than sucrose (table sugar), [4] [5] three times as sweet as both aspartame and acesulfame potassium, and twice as sweet as sodium saccharin. [4]

The commercial success of sucralose-based products stems from its favorable comparison to other low-calorie sweeteners in terms of taste, stability, and safety. [4] [6] It is commonly sold under the Splenda brand name. [4]

Uses

Sucralose is used in many food and beverage products because it is a no-calorie sweetener (3 calories per typical one gram serving), [3] does not promote dental cavities, [7] is safe for consumption by diabetics and nondiabetics, [8] and does not affect insulin levels, [9] although the powdered form of sucralose-based sweetener product Splenda (as most other powdered sucralose products) contains 95% (by volume) bulking agents dextrose and maltodextrin that do affect insulin levels.

Sucralose is used as a replacement for (or in combination with) other artificial or natural sweeteners such as aspartame, acesulfame potassium or high-fructose corn syrup. It is used in products such as candy, breakfast bars, coffee pods, and soft drinks. It is also used in canned fruits wherein water and sucralose take the place of much higher calorie corn syrup-based additives. Sucralose mixed with dextrose or maltodextrin (both made from corn) as bulking agents is sold internationally by McNeil Nutritionals under the Splenda brand name. In the United States and Canada, this blend is increasingly found in restaurants in yellow packets. [lower-alpha 1]

Cooking

Sucralose is available in a granulated form that allows same-volume substitution with sugar. [10] This mix of granulated sucralose includes fillers, all of which rapidly dissolve in water. Sucralose is not hygroscopic, which can lead to baked goods that are noticeably drier and manifest a less dense texture than those made with sucrose.[ citation needed ]

Unlike sucrose, which melts when baked at high temperatures, sucralose maintains its granular structure when subjected to dry, high heat (e.g., in a 180 °C or 350 °F oven). Furthermore, in its pure state, sucralose begins to decompose at 119 °C (246 °F). [11] In some recipes, such as crème brûlée , which require sugar sprinkled on top to partially or fully melt and crystallize, substituting sucralose does not result in the same surface texture, crispness, or crystalline structure.[ citation needed ]

Safety evaluation

Sucralose has been accepted as safe by several food safety regulatory bodies worldwide, including the U.S. Food and Drug Administration (FDA), the Joint FAO/WHO Expert Committee Report on Food Additives, the European Union's Scientific Committee on Food, Health Protection Branch of Health and Welfare Canada, and Food Standards Australia New Zealand.

Maximum acceptable daily intake

Various assessments have reported different amounts of maximum acceptable daily intake (ADI), usually measured as mg per kg of body weight. According to the Canadian Diabetes Association, the amount of sucralose that can be consumed over a person's lifetime without any adverse effects is 9 milligrams per kilogram of body weight per day. [12] [13] The FDA approval process indicated that consuming sucralose in typical amounts as a sweetener was safe. [13] [14] The intake at which adverse effects are seen is 1500 mg/kg BW/day, [14] providing a large margin of safety compared to the estimated daily intake. The European Food Safety Authority (EFSA) proposed an ADI of 5 mg per kg (body weight) while the FDA established it as 15 mg per kg body weight, that is, 350–1050 mg per day for a person of 70 kg. [13]

Metabolism

Most ingested sucralose is directly excreted in the feces, while about 11–27% is absorbed by the gastrointestinal tract (gut). [13] [14] The amount absorbed from the gut is largely removed from the blood by the kidneys and eliminated via urine, with 20–30% of absorbed sucralose being metabolized. [13] [14]

Possible health effects

In reviewing a 1987 food additive petition by McNeil Nutritionals, the FDA stated that "in the 2-year rodent bioassays... there was no evidence of carcinogenic activity for either sucralose or its hydrolysis products". [14] [15]

As of 2020, reviews of numerous safety and toxicology studies on sucralose concluded that it is not toxic or carcinogenic, even at levels of daily consumption much larger than those typically used. [13] [14] A 2023 FDA summary declared that there were no concerns of sucralose toxicity on cancer risk, metabolism, the reproductive system or the nervous system, and no concern for people with diabetes. [4]

Baking

At normal baking temperatures, sucralose is heat stable, indicating that it retains its sweetness and is suitable as a sugar substitute for use in baked goods. [4]

History

Sucralose was discovered in 1976 by scientists from Tate & Lyle, working with researchers Leslie Hough and Shashikant Phadnis at Queen Elizabeth College (now part of King's College London). [16] While researching novel uses of sucrose and its synthetic derivatives, Phadnis was told to "test" a chlorinated sugar compound. According to an anecdotal account, Phadnis thought Hough asked him to "taste" it, so he did and found the compound to be exceptionally sweet. [17]

Tate & Lyle patented the substance in 1976; as of 2008, the only remaining patents concerned specific manufacturing processes. [18]

A Duke University animal study funded by the Sugar Association [19] found evidence that doses of Splenda (containing ~1% sucralose and ~99% maltodextrin by weight) between 100 and 1000 mg/kg BW/day, containing sucralose at 1.1 to 11 mg/kg BW/day, fed to rats reduced gut microbiota, increased the pH level in the intestines, contributed to increases in body weight, and increased levels of P-glycoprotein (P-gp). [20] These effects have not been reported in humans. [5] An expert panel, including scientists from Duke University, Rutgers University, New York Medical College, Harvard School of Public Health, and Columbia University reported in Regulatory Toxicology and Pharmacology that the Duke study was "not scientifically rigorous and is deficient in several critical areas that preclude reliable interpretation of the study results". [21]

Sucralose was first approved for use in Canada in 1991. Subsequent approvals came in Australia in 1993, in New Zealand in 1996, in the United States in 1998, and in the European Union in 2004. By 2008, it had been approved in over 80 countries, including Mexico, Brazil, China, India, and Japan. [22] In 2006, the FDA amended the regulations for foods to include sucralose as a "non-nutritive sweetener" in food. [23] In May 2008, Fusion Nutraceuticals launched a generic product to the market, using Tate & Lyle patents.

In April 2015, PepsiCo announced that it would be moving from aspartame to sucralose for most of its diet drinks in the U.S. [24] due to sales of Diet Pepsi falling by more than 5% in the U.S. The company stated that its decision was a commercial one, responding to consumer preferences.

In February 2018, PepsiCo went back to using aspartame in Diet Pepsi because of an 8% drop in sales for the previous year. [25] [26]

Chemistry and production

Sucrose2.png
Sucralose2.png
Comparison of the chemical structures of sucrose (top) and sucralose (bottom)

Sucralose is a disaccharide composed of 1,6-dichloro-1,6-dideoxyfructose and 4-chloro-4-deoxygalactose. It is synthesized by the selective chlorination of sucrose in a multistep route that substitutes three specific hydroxyl groups with chlorine atoms. This chlorination is achieved by selective protection of one of the primary alcohols as an ester (acetate or benzoate), followed by chlorination with an excess of any of several chlorinating agent to replace the two remaining primary alcohols and one of the secondary alcohols, and then by hydrolysis of the ester. [27] [28]

Storage

Sucralose is stable when stored under normal conditions of temperature, pressure and humidity. [29] Upon prolonged heating during storage at elevated temperatures (38 °C, 100 °F), sucralose may break down, releasing carbon dioxide, carbon monoxide and minor amounts of hydrogen chloride. [29]

Effect on caloric content

Though sucralose contains minimal calories (3 per gram), [3] products that contain fillers such as dextrose and/or maltodextrin add about 2–4 calories per teaspoon or individual packet, depending on the product, the fillers used, brand, and the intended use of the product. [30] The FDA allows for any product containing fewer than 5 calories per serving to be labeled as "zero calories"; [31] a typical one gram serving packet of sucralose supplies 3 calories derived from its composition as 0.9 gram of carbohydrates and 0.1 gram of water. [3]

Research

There is no evidence of an effect of sucralose on long-term weight loss or body mass index, with cohort studies showing a minor effect on weight gain and heart disease risks. [32]

Environmental effects

According to one study, sucralose is digestible by a number of microorganisms and is broken down once released into the environment. [33] However, measurements by the Swedish Environmental Research Institute have shown sewage treatment has little effect on sucralose, which is present in wastewater effluents at levels of several μg/L (ppb). [34] No ecotoxicological effects are known at such levels, but the Swedish Environmental Protection Agency warns a continuous increase in levels may occur if the compound is only slowly degraded in nature. When heated to very high temperatures (over 350 °C or 662 °F) in metal containers, sucralose can produce polychlorinated dibenzo-p-dioxins and other persistent organic pollutants in the resulting smoke. [35]

Sucralose has been detected in natural waters, but research indicates that the levels found in the environment are far below those required to cause adverse effects to certain kinds of aquatic life. [36]

See also

Footnotes

  1. ↑ This is contrast to the blue packets commonly used for aspartame and pink ones containing saccharin sweeteners. In Canada, yellow packets are also associated with SugarTwin's cyclamate sweetener.

Related Research Articles

<span class="mw-page-title-main">Aspartame</span> Artificial non-saccharide sweetener

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 brand names NutraSweet, Equal, and Canderel. Aspartame was approved by the US Food and Drug Administration (FDA) in 1974, and then again in 1981, after approval was revoked in 1980.

<span class="mw-page-title-main">Stevia</span> Sweetener and sugar substitute

Stevia is a sweet sugar substitute that is about 50 to 300 times sweeter than sugar. It is extracted from the leaves of Stevia rebaudiana, a plant native to areas of Paraguay and Brazil in the southern Amazon rainforest. The active compounds in stevia are steviol glycosides. Stevia is heat-stable, pH-stable, and not fermentable. Humans cannot metabolize the glycosides in stevia, and therefore it has zero calories. Its taste has a slower onset and longer duration than that of sugar, and at high concentrations some of its extracts may have an aftertaste described as licorice-like or bitter. Stevia is used in sugar- and calorie-reduced food and beverage products as an alternative for variants with sugar.

<span class="mw-page-title-main">Splenda</span> Brand of sugar substitute

Splenda is a global brand of sugar substitutes and reduced-calorie food products. While the company is known for its original formulation containing sucralose, it also manufactures items using natural sweeteners such as stevia, monk fruit and allulose. It is owned by the American company Heartland Food Products Group. The high-intensity sweetener ingredient sucralose used in Splenda Original is manufactured by the British company Tate & Lyle.

<span class="mw-page-title-main">Sugar substitute</span> Sugarless food additive intended to provide a sweet taste

A sugar substitute is a food additive that provides a sweetness like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie or low-calorie sweetener. Artificial sweeteners may be derived through manufacturing of plant extracts or processed by chemical synthesis. Sugar substitute products are commercially available in various forms, such as small pills, powders, and packets.

<span class="mw-page-title-main">Xylitol</span> Synthetic sweetener

Xylitol is a chemical compound with the formula C
5H
12O
5, or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is freely soluble in water. It is classified as a polyalcohol and a sugar alcohol, specifically an alditol. The name derives from Ancient Greek: ξύλον, xyl[on] 'wood', with the suffix -itol used to denote it being a sugar alcohol.

<span class="mw-page-title-main">Saccharin</span> Chemical compound

Saccharin, also called saccharine, benzosulfimide, or E954, or used in saccharin sodium or saccharin calcium forms, is a non-nutritive artificial sweetener. Saccharin is a benzoic sulfimide that is about 500 times sweeter than sucrose, but has a bitter or metallic aftertaste, especially at high concentrations. It is used to sweeten products, such as drinks, candies, baked goods, tobacco products, excipients, and for masking the bitter taste of some medicines. It appears as white crystals and is odorless.

<span class="mw-page-title-main">Acesulfame potassium</span> Calorie-free sugar substitute

Acesulfame potassium, also known as acesulfame K or Ace K, is a synthetic calorie-free sugar substitute often marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG. In chemical structure, acesulfame potassium is the potassium salt of 6-methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide. It is a white crystalline powder with molecular formula C
4H
4KNO
4S and a molecular weight of 201.24 g/mol.

<span class="mw-page-title-main">Pepsi One</span> Brand of cola produced by Pepsi

Pepsi One, corporately styled PEPSI ONE, was a sugar-free cola, marketed by PepsiCo in the United States as an alternative to regular Pepsi and Diet Pepsi.

<span class="mw-page-title-main">Diet soda</span> Type of sugar-free or artificially sweetened soda

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<span class="mw-page-title-main">Erythritol</span> Chemical compound

Erythritol (, ) is an organic compound, the naturally occurring achiral meso four-carbon sugar alcohol (or polyol). It is the reduced form of either D- or L-erythrose and one of the two reduced forms of erythrulose. It is used as a food additive and sugar substitute. It is synthesized from corn using enzymes and fermentation. Its formula is C
4H
10O
4, or HO(CH2)(CHOH)2(CH2)OH.

<span class="mw-page-title-main">Neotame</span> Artificial sweetener

Neotame, also known by the trade name Newtame, is a non-caloric artificial sweetener and aspartame analog by NutraSweet. By mass, it is 8000 times sweeter than sucrose. It has no notable off-flavors when compared to sucrose. It enhances original food flavors. It can be used alone, but is often mixed with other sweeteners to increase their individual sweetness and decrease their off-flavors. It is chemically somewhat more stable than aspartame. Its use can be cost effective in comparison to other sweeteners as smaller amounts of neotame are needed.

<span class="mw-page-title-main">Maltodextrin</span> Polysaccharide of glucose

Maltodextrin is a name shared by two different families of chemicals. Both families are glucose polymers, but have little chemical or nutritional similarity.

<span class="mw-page-title-main">Diet Pepsi</span> Sugar-free, artificially sweetened soda

Diet Pepsi is a diet carbonated cola soft drink produced by PepsiCo, introduced in 1964 as a variant of Pepsi with no sugar. First test marketed in 1963 under the name Patio Diet Cola, it was re-branded as Diet Pepsi the following year, becoming the first diet cola to be distributed on a national scale in the United States. In the 1960s and 1970s, its competition consisted of the Coca-Cola Company's subsequently discontinued Tab. The United States represents the largest single market for Diet Pepsi.

<span class="mw-page-title-main">Tagatose</span> Chemical compound

Tagatose is a hexose monosaccharide. It is found in small quantities in a variety of foods, and has attracted attention as an alternative sweetener. It is often found in dairy products, because it is formed when milk is heated. It is similar in texture and appearance to sucrose :215 and is 92% as sweet,:198 but with only 38% of the calories.:209 Tagatose is generally recognized as safe by the Food and Agriculture Organization and the World Health Organization, and has been since 2001. Since it is metabolized differently from sucrose, tagatose has a minimal effect on blood glucose and insulin levels. Tagatose is also approved as a tooth-friendly ingredient for dental products. Consumption of more than about 30 grams of tagatose in a dose may cause gastric disturbance in some people, as it is mostly processed in the large intestine, similar to soluble fiber.:214

<span class="mw-page-title-main">Equal (sweetener)</span> Brand of food sweetener

Equal is an American brand of artificial sweetener containing aspartame, acesulfame potassium, dextrose and maltodextrin. It is marketed as a tabletop sweetener by Merisant, a global corporation which also previously owned the well-known NutraSweet brand when it was a subsidiary of Monsanto and which has headquarters in Chicago, Illinois, Switzerland, Mexico, and Singapore. In French Canada, Equal is known as "Égal".

<span class="mw-page-title-main">High-fructose corn syrup</span> Processed corn syrup

High-fructose corn syrup (HFCS), also known as glucose–fructose, isoglucose and glucose–fructose syrup, is a sweetener made from corn starch. As in the production of conventional corn syrup, the starch is broken down into glucose by enzymes. To make HFCS, the corn syrup is further processed by D-xylose isomerase to convert some of its glucose into fructose. HFCS was first marketed in the early 1970s by the Clinton Corn Processing Company, together with the Japanese Agency of Industrial Science and Technology, where the enzyme was discovered in 1965.

<span class="mw-page-title-main">Psicose</span> Chemical compound

D-Psicose (C6H12O6), also known as D-allulose, or simply allulose, is a low-calorie epimer of the monosaccharide sugar fructose, used by some major commercial food and beverage manufacturers as a low-calorie sweetener. First identified in wheat in the 1940s, allulose is naturally present in small quantities in certain foods.

Fruit2O, formerly manufactured by Kraft, is a lightly flavored, non-carbonated water beverage introduced in 1999. Fruit2o was introduced to compete not only with the bottled water market but also with the soft drink market. Sunny Delight Beverages purchased the Veryfine Products line from Kraft in 2007.

Russell L. Blaylock is an author and a retired U.S. neurosurgeon.

Truvia is a brand of stevia-based sugar substitute developed jointly by The Coca-Cola Company and Cargill. It is distributed and marketed by Cargill as a tabletop sweetener as well as a food ingredient. Truvia is made of stevia leaf extract, erythritol, and natural flavors. Because it comes from the stevia plant, Cargill classifies Truvia as a natural sweetener in addition to being a non-nutritive sweetener, although Cargill has settled lawsuits alleging deceptive marketing of Truvia as "natural". Since its launch in 2008, Truvia natural sweetener has become the second best-selling sugar substitute in units in the U.S. behind Splenda, surpassing Equal and Sweet'n Low. Truvia competes with Stevia In The Raw, the #2 brand of stevia, owned by Cumberland Packaging who also makes Sweet 'n Low.

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  34. ↑ "Measurements of Sucralose in the Swedish Screening Program 2007, Part I; Sucralose in surface waters and STP samples" (PDF).
  35. ↑ Dong S, Liu G, Hu J, Zheng M (October 2013). "Polychlorinated dibenzo-p-dioxins and dibenzofurans formed from sucralose at high temperatures". Scientific Reports. 3: 2946. Bibcode:2013NatSR...3E2946D. doi:10.1038/srep02946. PMC   3796739 . PMID   24126490.
  36. ↑ Stoddard KI, Huggett DB (October 2014). "Early life stage (ELS) toxicity of sucralose to fathead minnows, Pimephales promelas". Bulletin of Environmental Contamination and Toxicology. 93 (4): 383–387. Bibcode:2014BuECT..93..383S. doi:10.1007/s00128-014-1348-9. PMID   25120258. S2CID   5380255.
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