関: alditol

WordNet

sweeten with sugar; "sugar your tea" (同)saccharify
a white crystalline carbohydrate used as a sweetener and preservative (同)refined sugar
any of a series of volatile hydroxyl compounds that are made from hydrocarbons by distillation
a liquor or brew containing alcohol as the active agent; "alcohol (or drink) ruined him" (同)alcoholic drink, alcoholic_beverage, intoxicant, inebriant
with sweetening added (同)sweetened, sweet, sweet-flavored

PrepTutorEJDIC

〈U〉砂糖 / 〈C〉(1個・さじ1杯の)砂糖 / 〈U〉庶糖 / 《話》(恋人に対して呼び掛けて)ねえ / …‘に'砂糖を混ぜる(かける);…‘に'砂糖を加えて甘くする
『アルコール』,酒精 / 『アルコール飲料』,酒

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/10/11 02:21:23」(JST)

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A sugar alcohol is a kind of alcohol prepared from sugar.^[1] These organic compounds are a class of polyols, also called polyhydric alcohol, polyalcohol, or glycitol. They are white, water-soluble solids that occur naturally and 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 to counter the low sweetness. Unlike sugars, sugar alcohols do not contribute to the formation of tooth cavities.

Erythritol is a sugar alcohol. It is 60-70% as sweet as sugar but contributes considerably fewer calories when consumed.

Production and 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.

Sugar alcohols occur naturally and at one time, mannitol was obtained from natural sources. Today, they are often obtained by hydrogenation of sugars, using Raney nickel catalysts.^[1] The conversion of glucose and mannose to sorbitol and mannitol is given:

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 annually. Xylitol and lacticol are obtained similarly. Erythritol on the other hand is obtained by fermentation of glucose and sucrose.

Health effects

Of these, xylitol is perhaps the most popular due to its similarity to sucrose in visual appearance and sweetness.^{[citation needed]} Sugar alcohols do not contribute to tooth decay.^[2]^[3]

However, consumption of sugar alcohols does affect blood sugar levels, although less than that of "regular" sugar (sucrose). Sugar alcohols may also cause bloating and diarrhea when consumed in excessive amounts.^[4]

Common sugar alcohols

Methanol (1-carbon)
Ethylene glycol (2-carbon)
Glycerol (3-carbon)
Erythritol (4-carbon)
Threitol (4-carbon)

Arabitol (5-carbon)
Xylitol (5-carbon)
Ribitol (5-carbon)

Mannitol (6-carbon)
Sorbitol (6-carbon)
Galactitol (6-carbon)
Fucitol (6-carbon)
Iditol (6-carbon)
Inositol (6-carbon; a cyclic sugar alcohol)

Volemitol (7-carbon)
Isomalt (12-carbon)
Maltitol (12-carbon)
Lactitol (12-carbon)
Maltotriitol (18-carbon)
Maltotetraitol (24-carbon)
Polyglycitol

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.

The simplest sugar alcohols, ethylene glycol and methanol, are sweet but notoriously toxic chemicals used in antifreeze. The more complex sugar alcohols are for the most part nontoxic.

Sugar alcohols as food additives

Name	Sweetness relative to sucrose	Food energy (kcal/g)	Sweetness per food energy, relative to sucrose
Arabitol	0.7	0.2	14
Erythritol	0.812	0.213	15
Glycerol	0.6	4.3	0.56
HSH	0.4–0.9	3.0	0.52–1.2
Isomalt	0.5	2.0	1.0
Lactitol	0.4	2.0	0.8
Maltitol	0.9	2.1	1.7
Mannitol	0.5	1.6	1.2
Sorbitol	0.6	2.6	0.92
Xylitol	1.0	2.4	1.6
Compare with: Sucrose	1.0	4.0	1.0

As a group, sugar alcohols are not as sweet as sucrose, and they have less food energy than sucrose. Their flavor is like 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, one with a strong heat of solution.^[5]

Sugar alcohols are usually incompletely absorbed into the blood stream from the small intestines 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. However, like many other incompletely digestible substances, overconsumption of sugar alcohols can lead to bloating, diarrhea and flatulence because they are not 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. 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]^[4]

The table above 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.

References

^ ^a ^b ^c Hubert Schiweck, Albert Bär, Roland Vogel, Eugen Schwarz, Markwart Kunz, Cécile Dusautois, Alexandre Clement, Caterine Lefranc, Bernd Lüssem, Matthias Moser, Siegfried Peters "Sugar Alcohols" Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim. doi:10.1002/14356007.a25_413.pub3
^ ^a ^b "Role of Sugar-Free Foods and Medications in Maintaining Good Oral Health". American Dental Assoiation. 2002-06-05. Retrieved 2010-08-01.
^ ^a ^b Bradshaw, DJ; Marsh, PD (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.
^ ^a ^b "Eat any sugar alcohol lately?". Yale-New Haven Hospital. 2005-03-10. Retrieved 2012-06-25.
^ 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.

External links

"Sugar Alcohols". The Sugar Association, Inc. 2012. Retrieved 2012-10-10.
Sugar Alcohol Fact Sheet - An International Food Information Council publication

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English Journal

Characterisation of the turbid particles in the extraction of sugar beet pectins.

Guo XM1, Zhu SM1, Tang Q1, Yu SJ2.
Food chemistry.Food Chem.2014 Nov 1;162:99-103. doi: 10.1016/j.foodchem.2014.04.045. Epub 2014 Apr 24.
This paper was aimed at characterising the insoluble substances (IS) responsible for the turbidity of the extract and impurity of the resulting pectins. Results showed that the IS caused a significant increase in the turbidity of the extract. The IS had bi-pyramidal shapes under the SEM observation.
PMID 24874363

The impact of extraction with a chelating agent under acidic conditions on the cell wall polymers of mango peel.

Jamsazzadeh Kermani Z1, Shpigelman A1, Kyomugasho C1, Van Buggenhout S1, Ramezani M1, Van Loey AM1, Hendrickx ME2.
Food chemistry.Food Chem.2014 Oct 15;161:199-207. doi: 10.1016/j.foodchem.2014.03.131. Epub 2014 Apr 5.
The objective of this research was to evaluate whether mango peel is a potential source of functional cell wall polymers. To reach this objective, the native pectin polymers (NPP) extracted as alcohol insoluble residue from mango peel, were characterised in terms of uronic acid content, degree of me
PMID 24837941

A GC-MS-based metabolomics study on the tubers of commercial potato cultivars upon storage.

Uri C1, Juhász Z1, Polgár Z2, Bánfalvi Z3.
Food chemistry.Food Chem.2014 Sep 15;159:287-92. doi: 10.1016/j.foodchem.2014.03.010. Epub 2014 Mar 14.
Using gas chromatography-mass spectrometry (GC-MS) as a system for the detection of amino acids, organic acids, sugars, sugar alcohols, and fatty acids, we characterised six commercial potato cultivars (Hópehely, Katica, Lorett, Somogyi kifli, Vénusz Gold, and White Lady) with different pedigrees,
PMID 24767057

Japanese Journal

共生関係にひそむ第三者 : 花蜜を利用する酵母・細菌が変える植物-送粉者相互作用

牧野崇司,横山潤
日本生態学会誌 64(2), 101-115, 2014-07-30
生物間相互作用において第三者の存在がその進化的帰結を変えることが知られている。動物媒花と花粉を運ぶ送粉者の相互作用も例外ではなく、他の開花種や植食者などの第三者の影響を受ける。本稿で着目する酵母や細菌もまた、送粉者が得るべき蜜を横取りすることで花と送粉者の関係に変化をもたらすことが予想されるものの、彼らは肉眼では見えないこともあってほとんど注目されてこなかった。しかし近年の分子的手法の普及にともな …
NAID 110009851609

Production of mannitol from raw glycerol by Candida azyma

Yoshikawa Jun,Habe Hiroshi,Morita Tomotake [他]
Journal of bioscience and bioengineering 117(6), 725-729, 2014-06
NAID 40020094466

Production of mannitol from raw glycerol by Candida azyma(MICROBIAL PHYSIOLOGY AND BIOTECHNOLOGY)

Yoshikawa Jun,Habe Hiroshi,Morita Tomotake,Fukuoka Tokuma,Imura Tomohiro,Iwabuchi Hiroyuki,Uemura Shingo,Tamura Takamitsu,Kitamoto Dai
Journal of bioscience and bioengineering 117(6), 725-729, 2014-06
To promote the effective use of raw glycerol, 13 yeast strains with the ability to produce mannitol from glycerol were isolated from environmental samples. Of the 13 strains, strain 7-12G was selected …
NAID 110009823158