Sugar alcohol

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Erythritol is a sugar alcohol. It is 60-70% as sweet as sugar and almost noncaloric. Erythritol structure.svg
Erythritol is a sugar alcohol. It is 60–70% as sweet as sugar and almost noncaloric.

Sugar alcohols (also called polyhydric alcohols, polyalcohols, alditols or glycitols) are organic compounds, typically derived from sugars, containing one hydroxyl group (−OH) attached to each carbon atom. They are white, water-soluble solids that can occur naturally or be produced industrially by hydrogenating sugars. Since they contain multiple (−OH) groups, they are classified as polyols.

Contents

Sugar alcohols are used widely in the food industry as thickeners and sweeteners. In commercial foodstuffs, sugar alcohols are commonly used in place of table sugar (sucrose), often in combination with high-intensity artificial sweeteners, in order to offset their low sweetness. Xylitol and sorbitol are popular sugar alcohols in commercial foods. [1]

Structure

Sugar alcohols have the general formula HOCH2(CHOH)nCH2OH. In contrast, sugars have two fewer hydrogen atoms, for example, HOCH2(CHOH)nCHO or HOCH2(CHOH)n−1C(O)CH2OH. Like their parent sugars, sugar alcohols exist in diverse chain length. Most have five- or six-carbon chains, because they are derived respectively from pentoses (five-carbon sugars) and hexoses (six-carbon sugars), which are the more common sugars. They have one −OH group attached to each carbon. They are further differentiated by the relative orientation (stereochemistry) of these −OH groups. Unlike sugars, which tend to exist as rings, sugar alcohols do not, although they can be dehydrated to give cyclic ethers (e.g. sorbitan can be dehydrated to isosorbide).

Production

Sugar alcohols can be, and often are, produced from renewable resources. Particular feedstocks are starch, cellulose and hemicellulose; the main conversion technologies use H2 as the reagent: hydrogenolysis , i.e. the cleavage of C−O single bonds, converting polymers to smaller molecules, and hydrogenation of C=O double bonds, converting sugars to sugar alcohols. [2]

Sorbitol and mannitol

Mannitol is no longer obtained from natural sources; currently, sorbitol and mannitol are obtained by hydrogenation of sugars, using Raney nickel catalysts. [1] The conversion of glucose and mannose to sorbitol and mannitol is given as

HOCH2CH(OH)CH(OH)CH(OH)CH(OH)CHO + H2 → HOCH2CH(OH)CH(OH)CH(OH)CH(OH)CHHOH

Erythritol

Erythritol is obtained by the fermentation of glucose and sucrose.

Health effects

Sugar alcohols do not contribute to tooth decay; in fact, xylitol deters tooth decay. [3] [4]

Sugar alcohols are absorbed at 50% of the rate of sugars, resulting in less of an effect on blood sugar levels as measured by comparing their effect to sucrose using the glycemic index. [5] [6]

Common sugar alcohols

Both disaccharides and monosaccharides can form sugar alcohols; however, sugar alcohols derived from disaccharides (e.g. maltitol and lactitol) are not entirely hydrogenated because only one aldehyde group is available for reduction.

Sugar alcohols as food additives

This table presents the relative sweetness and food energy of the most widely used sugar alcohols. Despite the variance in food energy content of sugar alcohols, the European Union's labeling requirements assign a blanket value of 2.4 kcal/g to all sugar alcohols.

Properties of sugar alcohols[ additional citation(s) needed ]
NameRelative sweetness (%)a Food energy (kcal/g)bRelative food energy (%)b Glycemic index cMaximum non-laxative dose (g/kg body weight)Dental acidityd
Arabitol 700.25.0 ? ? ?
Erythritol 60–800.215.300.66–1.0+None
Glycerol 604.31083 ? ?
HSHs Tooltip Hydrogenated starch hydrolysates40–903.07535 ? ?
Isomalt 45–652.0502–90.3 ?
Lactitol 30–402.0505–60.34Minor
Maltitol 902.15335–520.3Minor
Mannitol 40–701.64000.3Minor
Sorbitol 40–702.66590.17–0.24Minor
Xylitol 1002.46012–130.3–0.42None
Footnotes:a = Sucrose is 100%. b = Carbohydrates, including sugars like glucose, sucrose, and fructose, are ~4.0 kcal/g and 100%. c = Glucose is 100 and sucrose is 60–68. d = Sugars, like glucose, sucrose, and fructose, are high. References: [7] [8] [9] [10] [11] [12]

Characteristics

As a group, sugar alcohols are not as sweet as sucrose, and they have slightly less food energy than sucrose. Their flavor is similar to sucrose, and they can be used to mask the unpleasant aftertastes of some high-intensity sweeteners.

Sugar alcohols are not metabolized by oral bacteria, and so they do not contribute to tooth decay. [3] [4] They do not brown or caramelize when heated.

In addition to their sweetness, some sugar alcohols can produce a noticeable cooling sensation in the mouth when highly concentrated, for instance in sugar-free hard candy or chewing gum. This happens, for example, with the crystalline phase of sorbitol, erythritol, xylitol, mannitol, lactitol and maltitol. The cooling sensation is due to the dissolution of the sugar alcohol being an endothermic (heat-absorbing) reaction, [1] one with a strong heat of solution. [13]

Absorption from the small intestine

Sugar alcohols are usually incompletely absorbed into the blood stream from the small intestine which generally results in a smaller change in blood glucose than "regular" sugar (sucrose). This property makes them popular sweeteners among diabetics and people on low-carbohydrate diets. As an exception, erythritol is actually absorbed in the small intestine and excreted unchanged through urine, so it contributes no calories even though it is rather sweet. [1] [14]

Side effects

Like many other incompletely digestible substances, overconsumption of sugar alcohols can lead to bloating, diarrhea and flatulence because they are not fully absorbed in the small intestine. Some individuals experience such symptoms even in a single-serving quantity. With continued use, most people develop a degree of tolerance to sugar alcohols and no longer experience these symptoms. [14]

Related Research Articles

Monosaccharides, also called simple sugars, are the simplest forms of sugar and the most basic units (monomers) from which all carbohydrates are built.

<span class="mw-page-title-main">Sugar</span> Sweet-tasting, water-soluble carbohydrates

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 sugars, are molecules made of two bonded monosaccharides; common examples are sucrose, lactose, and maltose. White sugar is a refined form of sucrose. In the body, compound sugars are hydrolysed into simple sugars.

<span class="mw-page-title-main">Fructose</span> Simple ketonic monosaccharide found in many plants

Fructose, or fruit sugar, is a ketonic simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed by the gut directly into the blood of the portal vein during digestion. The liver then converts both fructose and galactose into glucose, so that dissolved glucose, known as blood sugar, is the only monosaccharide present in circulating blood.

<span class="mw-page-title-main">Sucrose</span> Disaccharide made of glucose and fructose

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 C
12H
22O
11.

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

Sorbitol, less commonly known as glucitol, is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alcohol group (−CH2OH). Most sorbitol is made from potato starch, but it is also found in nature, for example in apples, pears, peaches, and prunes. It is converted to fructose by sorbitol-6-phosphate 2-dehydrogenase. Sorbitol is an isomer of mannitol, another sugar alcohol; the two differ only in the orientation of the hydroxyl group on carbon 2. While similar, the two sugar alcohols have very different sources in nature, melting points, and uses.

<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">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">Mannitol</span> Chemical compound

Mannitol is a type of sugar alcohol used as a sweetener and medication. It is used as a low calorie sweetener as it is poorly absorbed by the intestines. As a medication, it is used to decrease pressure in the eyes, as in glaucoma, and to lower increased intracranial pressure. Medically, it is given by injection or inhalation. Effects typically begin within 15 minutes and last up to 8 hours.

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

Lactitol is a disaccharide sugar alcohol produced from lactose. It is used as a replacement bulk sweetener for low calorie foods with 30–40% of the sweetness of sucrose. It is also used medically as a laxative.

<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">Maltitol</span> Sugar alcohol used as a sweetener

Maltitol is a sugar alcohol used as a sugar substitute and laxative. It has 75–90% of the sweetness of sucrose and nearly identical properties, except for browning. It is used to replace table sugar because it is half as calorific, does not promote tooth decay, and has a somewhat lesser effect on blood glucose. In chemical terms, maltitol is known as 4-O-α-glucopyranosyl-D-sorbitol. It is used in commercial products under trade names such as Lesys, Maltisweet and SweetPearl.

The tooth-friendly label distinguishes products which are non-cariogenic and non-erosive, i.e. safe for teeth. To replace sugar, toothfriendly products often contain sweeteners that are not fermented by the microflora of the dental plaque. Products that are certified as toothfriendly also do not contain excessive amounts of food acids.

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

Isomalt is a sugar substitute, a mixture of the two disaccharide alcohols 1,6-GPS and 1,1-GPM. It is used primarily for its sugar-like physical properties. It has little to no impact on blood sugar levels, and does not stimulate the release of insulin. It also does not promote tooth decay and is considered to be tooth-friendly. Its energy value is 2 kcal per gram, half that of sugars. It is less sweet than sugar, but can be blended with high-intensity sweeteners such as sucralose to create a mixture with the same sweetness as sucrose (‘sugar’).

Rocket candy, or R-Candy, is a type of rocket propellant for model rockets made with a form of sugar as a fuel, and containing an oxidizer. The propellant can be divided into three groups of components: the fuel, the oxidizer, and the (optional) additive(s). In the past, sucrose was most commonly used as fuel. Modern formulations most commonly use sorbitol for its ease of production. The most common oxidizer is potassium nitrate (KNO3). Potassium nitrate is most commonly found in tree stump remover. Additives can be many different substances, and either act as catalysts or enhance the aesthetics of the liftoff or flight. A traditional sugar propellant formulation is typically prepared in a 65:35 (13:7) oxidizer to fuel ratio. This ratio can vary from fuel to fuel based on the rate of burn, timing and use.

<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.

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

Isomaltulose is a disaccharide carbohydrate composed of glucose and fructose. It is naturally present in honey and sugarcane extracts and is also produced industrially from table sugar (sucrose) and used as a sugar alternative.

Hydrogenated starch hydrolysates (HSHs), also known as polyglycitol syrup, are mixtures of several sugar alcohols. Hydrogenated starch hydrolysates were developed by the Swedish company Lyckeby Starch in the 1960s. The HSH family of polyols is an approved food ingredient in Canada, Japan, and Australia. HSH sweeteners provide 40 to 90% sweetness relative to table sugar.

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.

Isomaltooligosaccharide (IMO) is a mixture of short-chain carbohydrates which has a digestion-resistant property. IMO is found naturally in some foods, as well as being manufactured commercially. The raw material used for manufacturing IMO is starch, which is enzymatically converted into a mixture of isomaltooligosaccharides.

References

  1. 1 2 3 4 Hubert Schiweck; Albert Bär; Roland Vogel; Eugen Schwarz; Markwart Kunz; Cécile Dusautois; Alexandre Clement; Caterine Lefranc; Bernd Lüssem; Matthias Moser; Siegfried Peters (2012). "Sugar Alcohols". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a25_413.pub3. ISBN   978-3-527-30673-2.
  2. ↑ Ruppert, Agnieszka M.; Weinberg, Kamil; Palkovits, Regina (2012). "Hydrogenolysis Goes Bio: From Carbohydrates and Sugar Alcohols to Platform Chemicals". Angewandte Chemie International Edition. 51 (11): 2564–2601. doi:10.1002/anie.201105125. PMID   22374680.
  3. 1 2 Bradshaw, D.J.; Marsh, P.D. (1994). "Effect of Sugar Alcohols on the Composition and Metabolism of a Mixed Culture of Oral Bacteria Grown in a Chemostat". Caries Research. 28 (4): 251–256. doi:10.1159/000261977. PMID   8069881.
  4. 1 2 Honkala S, Runnel R, Saag M, Olak J, Nõmmela R, Russak S, Mäkinen PL, Vahlberg T, Falony G, Mäkinen K, Honkala E (May 21, 2014). "Effect of erythritol and xylitol on dental caries prevention in children". Caries Res. 48 (5): 482–90. doi:10.1159/000358399. PMID   24852946. S2CID   5442856.
  5. ↑ Sue Milchovich, Barbara Dunn-Long: Diabetes Mellitus: A Practical Handbook, p. 79, 10th ed., Bull Publishing Company, 2011
  6. ↑ Paula Ford-Martin, Ian Blumer: The Everything Diabetes Book, p. 124, 1st ed., Everything Books, 2004
  7. ↑ Karl F. Tiefenbacher (16 May 2017). The Technology of Wafers and Waffles I: Operational Aspects. Elsevier Science. pp. 165–. ISBN   978-0-12-811452-0.
  8. ↑ Encyclopedia of Food Chemistry. Elsevier Science. 22 November 2018. pp. 266–. ISBN   978-0-12-814045-1.
  9. ↑ Mäkinen KK (2016). "Gastrointestinal Disturbances Associated with the Consumption of Sugar Alcohols with Special Consideration of Xylitol: Scientific Review and Instructions for Dentists and Other Health-Care Professionals". Int J Dent. 2016: 5967907. doi: 10.1155/2016/5967907 . PMC   5093271 . PMID   27840639.
  10. ↑ Kathleen A. Meister; Marjorie E. Doyle (2009). Obesity and Food Technology. Am Cncl on Science, Health. pp. 14–. GGKEY:2Q64ACGKWRT.
  11. ↑ Kay O'Donnell; Malcolm Kearsley (13 July 2012). Sweeteners and Sugar Alternatives in Food Technology. John Wiley & Sons. pp. 322–324. ISBN   978-1-118-37397-2.
  12. ↑ Lyn O'Brien-Nabors (6 September 2011). Alternative Sweeteners, Fourth Edition. CRC Press. pp. 259–. ISBN   978-1-4398-4614-8.
  13. ↑ Cammenga, HK; LO Figura; B Zielasko (1996). "Thermal behaviour of some sugar alcohols". Journal of Thermal Analysis. 47 (2): 427–434. doi:10.1007/BF01983984. S2CID   98559442.
  14. 1 2 "Eat Any Sugar Alcohol Lately?". Yale New Haven Health. 2005-03-10. Retrieved January 6, 2018.
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