Chemistry:Sugar alcohol

From HandWiki
Short description: Organic compounds
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.

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 renewables. Particular feedstocks are starch, cellulose and hemicellulose, and the main conversion technologies are hydrogenolysis, i.e. the cleavage of C−O bonds, and hydrogenation of C=O double bonds, both using H2 as the reagent. Hydrogenolysis converts polymers to smaller molecules. Hydrogenation converts 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]
Name Relative sweetness (%)a Food energy (kcal/g)b Relative food energy (%)b Glycemic indexc Maximum non-laxative dose (g/kg body weight) Dental acidityd
Arabitol 70 0.2 5.0 ? ? ?
Erythritol 60–80 0.21 5.3 0 0.66–1.0+ None
Glycerol 60 4.3 108 3 ? ?
HSHs 40–90 3.0 75 35 ? ?
Isomalt 45–65 2.0 50 2–9 0.3 ?
Lactitol 30–40 2.0 50 5–6 0.34 Minor
Maltitol 90 2.1 53 35–52 0.3 Minor
Mannitol 40–70 1.6 40 0 0.3 Minor
Sorbitol 40–70 2.6 65 9 0.17–0.24 Minor
Xylitol 100 2.4 60 12–13 0.3–0.42 None
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]

References

  1. ↑ 1.0 1.1 1.2 1.3 Hubert Schiweck; Albert Bär; Roland Vogel; Eugen Schwarz; Markwart Kunz; Cécile Dusautois; Alexandre Clement; Caterine Lefranc et al. (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. ↑ 3.0 3.1 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. ↑ 4.0 4.1 "Effect of erythritol and xylitol on dental caries prevention in children". Caries Res. 48 (5): 482–90. May 21, 2014. doi:10.1159/000358399. PMID 24852946. 
  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. https://books.google.com/books?id=jysUDgAAQBAJ&pg=PA165. 
  8. ↑ Encyclopedia of Food Chemistry. Elsevier Science. 22 November 2018. pp. 266–. ISBN 978-0-12-814045-1. https://books.google.com/books?id=MTV8DwAAQBAJ&pg=PA266. 
  9. ↑ "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. 2016. doi:10.1155/2016/5967907. PMID 27840639. 
  10. ↑ Kathleen A. Meister; Marjorie E. Doyle (2009). Obesity and Food Technology. Am Cncl on Science, Health. pp. 14–. GGKEY:2Q64ACGKWRT. https://books.google.com/books?id=8zdeA2QZjJQC&pg=PA14. 
  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. https://books.google.com/books?id=3Mnwdwx2xDgC&pg=PT322. 
  12. ↑ Lyn O'Brien-Nabors (6 September 2011). Alternative Sweeteners, Fourth Edition. CRC Press. pp. 259–. ISBN 978-1-4398-4614-8. https://books.google.com/books?id=coDPwzFX7rAC&pg=PA259. 
  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. 
  14. ↑ 14.0 14.1 "Eat Any Sugar Alcohol Lately?". Yale New Haven Health. 2005-03-10. https://www.ynhh.org/services/nutrition/sugar-alcohol.aspx. 

External links

fr:Polyol



Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Sugar_alcohol&oldid=3336074"