7/8/2020 Sugar alcohol - Wikipedia

Sugar alcohol
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
hydrogenation of sugars. Since they contain multiple –OH groups,
they are classified as polyols.
Erythritol is a sugar alcohol. It is 60–
Sugar alcohols are used widely in the food industry as thickeners 70% as sweet as sugar but
and sweeteners. In commercial foodstuffs, sugar alcohols are contributes considerably fewer
commonly used in place of table sugar (sucrose), often in calories when consumed.
combination with high-intensity artificial sweeteners, in order to
offset their low sweetness. Xylitol and sorbitol are popular sugar
alcohols in commercial foods.[1]

Contents
Chemical structure
Production
Sorbitol and mannitol
Erythritol
Health effects
Common sugar alcohols
Sugar alcohols as food additives
Characteristics
Absorption from the small intestine
Side effects
See also
References
External links

Chemical 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. The sugar
alcohols differ in chain length. Most have five- or six-carbon chains, because they are derived from
pentoses (five-carbon sugars) and hexoses (six-carbon sugars), respectively. 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. They can, however,
be dehydrated to give cyclic ethers, e.g. sorbitol can be dehydrated to isosorbide.
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Production

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

More than a million tons of sorbitol are produced in this way every year. Xylitol and lactitol are obtained
similarly.

Erythritol

Erythritol is obtained by the fermentation of glucose and sucrose.

Health effects
Sugar alcohols do not contribute to tooth decay; on the contrary, xylitol is a deterrent to tooth decay.
[2][3]

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.[4][5] The unabsorbed
sugar alcohols may cause bloating and diarrhea due to their osmotic effect, if consumed in sufficient
amounts.[6]

Common sugar alcohols

Ethylene glycol (2- Arabitol (5-carbon) Mannitol (6-carbon) Volemitol (7-
carbon) Xylitol (5-carbon) Sorbitol (6-carbon) carbon)
Glycerol (3-carbon) Ribitol (5-carbon) Galactitol (6-carbon) Isomalt (12-
Erythritol (4-carbon) carbon)
Fucitol (6-carbon)
Threitol (4-carbon) Maltitol (12-
Iditol (6-carbon)
carbon)
Inositol (6-carbon; a cyclic
Lactitol (12-
sugar alcohol)
carbon)
Maltotriitol (18-
carbon)
Maltotetraitol (24-
carbon)
Polyglycitol

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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, EU labeling requirements assign a blanket
value of 2.4 kcal/g to all sugar alcohols.

Properties of sugar alcohols

Relative Food Relative
Glycemic Maximum non-laxative Dental
Name sweetness energy food energy
indexc dose (g/kg body weight) acidityd
(%)a (kcal/g)b (%)b
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.[2][3]
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

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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][6]

Side effects

However, 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.

See also
Sugar substitute

References
1. 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 (https://doi.org/10.1002%2F14356007.a25_413.pub3).
ISBN 978-3527306732.
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 (https://doi.org/10.1159%2F000261977). PMID 8069881 (https://pubmed.nc
bi.nlm.nih.gov/8069881).
3. 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 (https://doi.org/10.1159%2F00035839
9). PMID 24852946 (https://pubmed.ncbi.nlm.nih.gov/24852946).
4. Sue Milchovich, Barbara Dunn-Long: Diabetes Mellitus: A Practical Handbook, p. 79, 10th ed., Bull
Publishing Company, 2011
5. Paula Ford-Martin, Ian Blumer: The Everything Diabetes Book, p. 124, 1st ed., Everything Books,
2004
6. "Eat Any Sugar Alcohol Lately?" (https://www.ynhh.org/services/nutrition/sugar-alcohol.aspx). Yale
New Haven Health. 2005-03-10. Retrieved January 6, 2018.
7. Karl F. Tiefenbacher (16 May 2017). The Technology of Wafers and Waffles I: Operational Aspects (h
ttps://books.google.com/books?id=jysUDgAAQBAJ&pg=PA165). Elsevier Science. pp. 165–.
ISBN 978-0-12-811452-0.
8. Encyclopedia of Food Chemistry (https://books.google.com/books?id=MTV8DwAAQBAJ&pg=PA26
6). 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" (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5093271). Int J
Dent. 2016: 5967907. doi:10.1155/2016/5967907 (https://doi.org/10.1155%2F2016%2F5967907).
PMC 5093271 (https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5093271). PMID 27840639 (https://pu
bmed.ncbi.nlm.nih.gov/27840639).
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10. Kathleen A. Meister; Marjorie E. Doyle (2009). Obesity and Food Technology (https://books.google.c
om/books?id=8zdeA2QZjJQC&pg=PA14). 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 (https://books.google.com/books?id=3Mnwdwx2xDgC&pg=PT322). John Wiley & Sons.
pp. 322–324. ISBN 978-1-118-37397-2.
12. Lyn O'Brien-Nabors (6 September 2011). Alternative Sweeteners, Fourth Edition (https://books.googl
e.com/books?id=coDPwzFX7rAC&pg=PA259). 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 (https://doi.org/10.1007%2FBF0198
3984).

External links
"The Other 26 Sweeteners" (http://www.sugar.org/all-about-sugar/the-other-26-sweeteners/). The
Sugar Association, Inc. Retrieved 2015-06-03.
Sugar Alcohol Fact Sheet (http://www.foodinsight.org/Resources/Detail.aspx?topic=Sugar_Alcohols_
Fact_Sheet) – An International Food Information Council publication

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