グルシトール

外観

白色の結晶性粉末

定義

本品は、次の化学式で表される六価のアルコールである。

溶解性

水に溶けやすく、熱エタノールにやや溶けやすい。

解説

C6H14O6(182.17)．D-ソルビトールともいう．ヘキシトールの一種．D-マンニトール，D-ガラクチトールと同様に広く植物界に分布する．とくにヨーロッパ産のミヤマナナカマドSorbus aucupariaや日本産のS.commixta Hedlundの果実では5～10％，紅藻Bostrychia scorpoidesには13.6％ も含まれる．これらから抽出されるほか，D-グルコースの還元により合成される．吸湿性の結晶．無水物の融点112 ℃．[α]_D"－1.9°(水)．＋7°(ホウ砂水)．水，エタノールに可溶．甘味がある．Acetobacter xylinum，A.suboxydansなどの細菌により，選択的に酸化されてL-ソルボースを生じる．グルシトールは，ビタミンCの合成原料，皮革などの軟化剤，不凍剤，糖尿病患者用の甘味料，利尿剤，そのほか利用範囲が広い．LD50 15900 mg/kg(ラット，経口)．森北出版「化学辞典（第2版）

用途

食品添加物（甘味料）、化粧品用

用途

有機合成原料(ソルボース、ソルビタン)、甘味料研究用。

化粧品の成分用途

保湿.湿潤剤、保水剤、香料、香味剤

効能

診断補助薬 (造影補助), 緩下剤, 灌流液, 賦形剤, 栄養補給剤

商品名

D−ソルビトール (丸石製薬); D−ソルビトール (丸石製薬); D−ソルビトール (興和); ウロマチック (バクスター)

使用上の注意

アルゴン封入

化学的特性

Sorbitol is D-glucitol. It is a hexahydric alcohol related to mannose and is isomeric with mannitol.
Sorbitol occurs as an odorless, white or almost colorless, crystalline, hygroscopic powder. Four crystalline polymorphs and one amorphous form of sorbitol have been identified that have slightly different physical properties, e.g. melting point. Sorbitol is available in a wide range of grades and polymorphic forms, such as granules, flakes, or pellets that tend to cake less than the powdered form and have more desirable compression characteristics. Sorbitol has a pleasant, cooling, sweet taste and has approximately 50–60% of the sweetness of sucrose.

天然物の起源

Sorbitol is one of the most widely found sugar alcohols in nature with relatively high concentrations occurring in apples, pears, plums, peaches and apricots. Also reported found in several varieties of berries, seaweed and algae.

使用

Sorbitol is a humectant that is a polyol (polyhydric alcohol) produced by hydrogenation of glucose with good solubility in water and poor solubility in oil. It is approximately 60% as sweet as sugar, and has a caloric value of 2.6 kcal/g. It is highly hygroscopic and has a pleasant, sweet taste. It maintains moistness in shredded coconut, pet foods, and candy. In sugarless frozen desserts, it depresses the freezing point, adds solids, and contributes some sweetness. It is used in low-calorie beverages to provide body and taste. It is used in dietary foods such as sugarless candy, chewing gum, and ice cream. It is also used as a crystallization modifier in soft sugar-based confections.

定義

ChEBI: The D-enantiomer of glucitol (also known as D-sorbitol).

製造方法

Sorbitol is manufactured by hydrogenation of glucose with hydrogen and active nickel catalyst. It is commercially available as 70% syrup or as a pure white powder.

調製方法

Sorbitol occurs naturally in the ripe berries of many trees and plants. It was first isolated in 1872 from the berries of the Mountain Ash (Sorbus americana).
Industrially, sorbitol is prepared by high-pressure hydrogenation with a copper–chromium or nickel catalyst, or by electrolytic reduction of glucose and corn syrup. If cane or beet sugars are used as a source, the disaccharide is hydrolyzed to dextrose and fructose prior to hydrogenation.

一般的な説明

Odorless colorless solid. Sinks and mixes with water.

空気と水の反応

Water soluble.

反応プロフィール

D-Sorbitol is an alcohol. Flammable and/or toxic gases are generated by the combination of alcohols with alkali metals, nitrides, and strong reducing agents. They react with oxoacids and carboxylic acids to form esters plus water. Oxidizing agents convert them to aldehydes or ketones. Alcohols exhibit both weak acid and weak base behavior. They may initiate the polymerization of isocyanates and epoxides.

健康ハザード

Hot liquid will burn skin.

応用例（製薬）

Sorbitol is widely used as an excipient in pharmaceutical formulations. It is also used extensively in cosmetics and food products.
Sorbitol is used as a diluent in tablet formulations prepared by either wet granulation or direct compression. It is particularly useful in chewable tablets owing to its pleasant, sweet taste and cooling sensation. In capsule formulations it is used as a plasticizer for gelatin. Sorbitol has been used as a plasticizer in film formulations.
In liquid preparations sorbitol is used as a vehicle in sugar-free formulations and as a stabilizer for drug, vitamin, and antacid suspensions. Furthermore, sorbitol is used as an excipient in liquid parenteral biologic formulations to provide effective protein stabilization in the liquid state. It has also been shown to be a suitable carrier to enhance the in vitro dissolution rate of indometacin. In syrups it is effective in preventing crystallization around the cap of bottles. Sorbitol is additionally used in injectable and topical preparations, and therapeutically as an osmotic laxative.
Sorbitol may also be used analytically as a marker for assessing liver blood flow.

安全性プロファイル

Mildly toxic by ingestion. Human systemic effects by ingestion: hypermotility and diarrhea. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.

安全性

Sorbitol is widely used in a number of pharmaceutical products and occurs naturally in many edible fruits and berries. It is absorbed more slowly from the gastrointestinal tract than sucrose and is metabolized in the liver to fructose and glucose. Its caloric value is approximately 16.7 J/g (4 cal/g). Sorbitol is better tolerated by diabetics than sucrose and is widely used in many sugar-free liquid vehicles. However, it is not considered to be unconditionally safe for diabetics.
Reports of adverse reactions to sorbitol are largely due to its action as an osmotic laxative when ingested orally,(17–19) which may be exploited therapeutically. Ingestion of large quantities of sorbitol (>20 g/day in adults) should therefore be avoided. Sorbitol is not readily fermented by oral microorganisms and has little effect on dental plaque pH; hence, it is generally considered to be noncariogenic.
Sorbitol is generally considered to be more irritating than mannitol.
LD50 (mouse, IV): 9.48 g/kg
LD50 (mouse, oral): 17.8 g/kg
LD50 (rat, IV): 7.1 g/kg
LD50 (rat, SC): 29.6 g/kg

貯蔵

Sorbitol is chemically relatively inert and is compatible with most excipients. It is stable in air in the absence of catalysts and in cold, dilute acids and alkalis. Sorbitol does not darken or decompose at elevated temperatures or in the presence of amines. It is nonflammable, noncorrosive, and nonvolatile.
Although sorbitol is resistant to fermentation by many microorganisms, a preservative should be added to sorbitol solutions. Solutions may be stored in glass, plastic, aluminum, and stainless steel containers. Solutions for injection may be sterilized by autoclaving.
The bulk material is hygroscopic and should be stored in an airtight container in a cool, dry place.

純化方法

Crystallise D(-)-sorbitol (as hemihydrate) several times from EtOH/water (1:1), then dry it by fusing and storing over anhydrous MgSO4. [Koch et al. J Am Chem Soc 75 953 1953, Beilstein 1 IV 2839.]

不和合性

Sorbitol will form water-soluble chelates with many divalent and trivalent metal ions in strongly acidic and alkaline conditions. Addition of liquid polyethylene glycols to sorbitol solution, with vigorous agitation, produces a waxy, water-soluble gel with a melting point of 35–40℃. Sorbitol solutions also react with iron oxide to become discolored.
Sorbitol increases the degradation rate of penicillins in neutral and aqueous solutions.

規制状況(Regulatory Status)

GRAS listed. Accepted for use as a food additive in Europe. Included in the FDA Inactive Ingredients Database (intra-articular and IM injections; nasal; oral capsules, solutions, suspensions, syrups and tablets; rectal, topical, and vaginal preparations). Included in parenteral and nonparenteral medicines licensed in the UK. Included in the Canadian List of Acceptable Non-medicinal Ingredients.