Sorbitol

Base Information

• Chemical Name: Sorbitol
• CAS No.: 50-70-4
• Deprecated CAS: 15060-73-8,36134-87-9,3959-53-3,63800-20-4,75398-79-7,8013-15-8,8014-89-9,8036-93-9,8042-39-5,8045-74-7,8046-05-7,98201-93-5,952319-42-5,36134-87-9,3959-53-3,63800-20-4,8013-15-8,8014-89-9,8036-93-9,8042-39-5,8045-74-7,8046-05-7,952319-42-5,98201-93-5
• Molecular Formula: C6H14O6
• Molecular Weight: 182.174
• Hs Code.: 2905.44 Oral rat LD50: 15900 mg/kg
• European Community (EC) Number: 200-061-5
• ICSC Number: 0892
• NSC Number: 759608
• UNII: 506T60A25R
• DSSTox Substance ID: DTXSID5023588
• Nikkaji Number: J2.299C
• Wikipedia: Sorbitol
• Wikidata: Q245280
• NCI Thesaurus Code: C29462
• RXCUI: 9945
• Metabolomics Workbench ID: 37159
• ChEMBL ID: CHEMBL1682
• Mol file: 50-70-4.mol

Synonyms:Sorbitol syrup C;Sorbitur;Sorbogem 712;Sorbostyl;Sorbitol Powder;Sorbitol (7CI);(-)-Sorbitol;C*Sorbidex;C*Sorbidex P 16616;CSorbidex 16100;Cholaxine;Cystosol;D-Sorbit 50M;Glucarine;Glucitol;Karion;Karioninstant;L-Gulitol;Multitol;NSC 25944;Neosorb;Neosorb 20/60DC;Neosorb 70/02SB;Neosorb 70/70;Neosorb P 60;Nivitin;Resulax;Sionit K;Sionite;Siosan;Sorbex R;Sorbex Rp;Sorbex S;Sorbidex S 16601;Sorbit LTSP;Sorbit T 70;Sorbit W-Powder;Sorbit WP;Sorbitol F;Sorbitol FP;Sorbitol S;

Chemical Property of Sorbitol

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: <0.1 mm Hg ( 25 °C)
• Melting Point: 98-100 °C(lit.)
• Refractive Index: 1.4600
• Boiling Point: 494.9 °C at 760 mmHg
• PKA: pKa (17.5°): 13.6
• Flash Point: 292.5 °C
• PSA: 121.38000
• Density: 1.596 g/cm³
• LogP: -3.58540
• Storage Temp.: Store at RT.
• Sensitive.: Hygroscopic
• Solubility.: H2O: 1 M at 20 °C, clear, colorless
• Water Solubility.: SOLUBLE
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 182.07903816
• Heavy Atom Count: 12
• Complexity: 105

Purity/Quality:

99% ^*data from raw suppliers

Sorbitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 8-36-26-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Biological Agents -> Monosaccharides and Derivatives
• Canonical SMILES: C(C(C(C(C(CO)O)O)O)O)O
• Isomeric SMILES: C([C@H]([C@H]([C@@H]([C@H](CO)O)O)O)O)O
• Recent ClinicalTrials: Metabolic Cofactor Supplementation in Alzheimer's Disease (AD) and Parkinson's Disease (PD) Patients
• Recent NIPH Clinical Trials: Questionnaire survey on bitterness of asenapine
• Inhalation Risk: A nuisance-causing concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance may cause effects on the gastrointestinal tract.
• Uses: 1. Daily chemical industry Sorbitol can be used as an excipient, moisturizing agents, and antifreeze agents in toothpaste, with the added amount being up to 25 to 30%. This can help maintain the lubrication, color, and good taste for the paste. In cosmetics field, it is used as an anti-drying agent (substitute glycerol) which can enhance the stretch and lubricity of emulsifier, and thus is suitable for long-term storage; Sorbitan esters and sorbitan fatty acid ester as well as its ethylene oxide adducts having a advantage of a small skin irritation which is thus widely used in the cosmetics industry. 2. The food industry Adding sorbitol into foods can prevent the drying of food and make food stay fresh and soft. Application in bread cake has a significant effect. The sweetness of sorbitol is lower than that of sucrose, and can’t be exploited by any bacteria. It is an important raw material for production of sugar-free candy and a variety of anti-caries food. Since the metabolism of the product does not cause increase of blood sugar, it can also be applied as a sweetener agent and nutrient agent for the food of patients with diabetes. Sorbitol does not contain an aldehyde group and is not easily oxidized. It will not have Maillard reaction with amino acids upon heating. It also has certain physiological activity. It can prevent the denaturation of the carotenoids and edible fats and protein; adding this product to the concentrated milk can extend the shelf life; it can also be used to improve the color, flavor and taste of small intestine and has significant stabilizing effect and long-term storage effect on fish pate. Similar effect can also be observed in the jam. 3. the pharmaceutical industry Sorbitol can be used as raw material in vitamin C; also can be used as feed syrup, injection fluids, and raw material of medicine tablet; as a drug dispersion agent and fillers, cryoprotectants, anti-crystallizing agent, medicine stabilizers, wetting agents, capsules plasticized agents, sweetening agents, and ointment matrix. 4. the chemical industry Sorbitol abietin is often used as the raw material for common architectural coatings, also used as plasticizers and lubricants for application in polyvinyl chloride resin and other polymers. It can from complex with iron, copper, and aluminum ion in alkaline solution to be applied to the washing and bleaching in textile industry. Using sorbitol and propylene oxide as a starting material can produce rigid polyurethane foam as well as have some flame retardant properties. The above information is edited by the lookchem of Dai Xiongfeng. D-Sorbitol is a sugar alcohol that is naturally found in Toyon berries. D-Sorbitol is used to increase stability of silver nanoparticles and is also used as a sugar substitute. 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. In manufacture of sorbose, ascorbic acid, propylene glycol, synthetic plasticizers and resins; as humectant (moisture conditioner) on printing rolls, in leather, tobacco. In writing inks to insure a smooth flow and to prevent crusting on the point of the pen. In antifreeze mixtures with glycerol or glycols. In candy manufacture of to increase shelf life by retarding the solidification of sugar; as humectant and softener in shredded coconut and peanut butter; as texturizer in foods; as sequestrant in soft drinks and wines. Used to reduce the undesirable aftertaste of saccharin in foodstuffs; as sugar substitute for diabetics. Pharmaceutic aid (flavor; tablet excipient); to increase absorption of vitamins and other nutrients in pharmaceutical preparations: Chem. Eng. News 36, 59 (Feb. 24, 1958).
• Production method: 1. Pour the prepared 53% aqueous solution of glucose into the autoclave, adding the nickel catalyst of 0.1% the weight of glucose; after replacement of the air, add hydrogen at about 3.5MPa, 150 °C, and pH8.2-8.4; control the endpoint with residual sugar content being lower than 0.5%. After precipitation for 5 min, put the resulting solution of sorbitol through ion exchange resin to obtain the refined product. Material fixed consumption amount: hydrochloric acid 19kg/t, caustic 36kg/ t, solid base 6kg/t, aluminum-nickel alloy powder 3kg/t, orally administrated glucose 518kg/t, activated carbon 4kg/t. 2. It is obtained from the hydrogenation of glucose with the nickel catalyst at high temperature and high pressure after which the product is further refined through the ion exchange resin, concentrated,crystallized, and, separated to obtain the final product. 3. Domestic production of sorbitol mostly applied continuously or intermittently hydrogenation of refined glucose obtained from starch saccharification: C6H12O6 + H2 [Ni] → C6H14O6 Pour the prepared 53% aqueous solution of glucose into the autoclave, adding the nickel catalyst of 0.1% the weight of glucose; after replacement of the air, add hydrogen at about 3.5MPa, 150 °C, and pH8.2-8.4; control the endpoint with residual sugar content being lower than 0.5%. After precipitation for 5 min, put the resulting solution of sorbitol through ion exchange resin to obtain the refined product. The above-mentioned process is simple without the necessity of isolation before obtaining qualified products as well as without "three wastes" pollution. However, for the starch, the yield is only 50%, and thus has a higher cost. Introduction of new technology by direct hydrogenation on starch saccharification liquid can obtain a yield up to 85%.
• Therapeutic Function: Cholecystokinetic, Diuretic, Pharmaceutic aid

Technology Process of Sorbitol

There total 361 articles about Sorbitol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 57.0%

Cellobiose (13360-52-6) → β-D-glucose (492-61-5) + D-sorbitol (50-70-4) + β-D-Glcp-(1->4)-D-glucitol (535-94-4)

Guidance literature:

With water; hydrogen; at 180 ℃; for 1h; under 37503.8 Torr; High pressure;

DOI:10.1007/s11426-018-9321-0

Reference yield:

Glycolaldehyde (141-46-8) → 1,2,3,4-butanetetrol (2319-57-5,2418-52-2,6968-16-7,7493-90-5,7541-59-5,10030-58-7,188346-77-2,149-32-6) + sorbitol (50-70-4,69-65-8,87-78-5,133-43-7,488-44-8,488-45-9,608-66-2,643-01-6,643-03-8,5552-13-6,6706-59-8,24557-79-7,25878-23-3,26566-34-7,45007-61-2,60660-56-2,60660-57-3,60660-58-4,132747-27-4)

Guidance literature:

Glycolaldehyde; With L-proline; In water; at 20 ℃;

With sodium tetrahydroborate; In methanol; at 0 ℃; Title compound not separated from byproducts;

DOI:10.1002/chem.200500139

Reference yield:

cellulose (9004-34-6) → propylene glycol (57-55-6,63625-56-9) + 1,2,3,4-butanetetrol (2319-57-5,2418-52-2,6968-16-7,7493-90-5,7541-59-5,10030-58-7,188346-77-2,149-32-6) + ethylene glycol (107-21-1) + sorbitol (50-70-4,69-65-8,87-78-5,133-43-7,488-44-8,488-45-9,608-66-2,643-01-6,643-03-8,5552-13-6,6706-59-8,24557-79-7,25878-23-3,26566-34-7,45007-61-2,60660-56-2,60660-57-3,60660-58-4,132747-27-4)

Guidance literature:

With hydrogen; In water; at 199.84 ℃; for 0.5h; under 45004.5 Torr; Autoclave;

DOI:10.1039/c2gc36088h

upstream raw materials:

D-Fructose

L-sorbose

fructose

D-glucose

Downstream raw materials:

1-[2-(furan-2-yl)-5-hydroxy-6-(hydroxymethyl)-1,3-dioxan-4-yl]ethane-1,2-diol

O¹,O³;O²,O⁴;O⁵,O⁶-((R,S,S)-trifurfurylidene)-D-glucitol

O¹,O³;O²,O⁴-dimethanediyl-D-glucitol

(1S,5R,6R)-5-<(4R)-1,3-dioxolan-4-yl>-2,4,7,9-tetraoxabicyclo<4.4.0>decane

Refernces

• 1、 Messer,Trifonoff,Stern,Collins,Bradbury. "Structure of a marsupial-mild trisaccharide.". . p. 327 - 334. Retrieved 1980.
• 2、 Upare, Pravin P.,Hwang, Young Kyu,Kim, Jin Chul,Lee, Jeong Hyeon,Kwak, Sang Kyu,Hwang, Dong Won. "A Robust and Highly Selective Catalytic System of Copper–Silica Nanocomposite and 1-Butanol in Fructose Hydrogenation to Mannitol". . p. 5050 - 5057. Retrieved 2020.
• 3、 Mandal, Soumitra,Maity, Kankan K.,Bhunia, Sanjoy K.,Dey, Biswajit,Patra, Sukesh,Sikdar, Samir R.,Islam, Syed S.. "Chemical analysis of new water-soluble (1→6)-, (1→4)-α, β-glucan and water-insoluble (1→3)-, (1→4)-β-glucan (Calocyban) from alkaline extract of an edible mushroom, Calocybe indica (Dudh Chattu)". . p. 2657 - 2663. Retrieved 2010.
• 4、 Kanwal, Nayab,Adhikari, Achyut,Hameed, Abdul,Hafizur, Rahman M.,Musharraf, Syed Ghulam. "Isolation and characterization of non-sulfated and sulfated triterpenoid saponins from Fagonia indica". . p. 151 - 159. Retrieved 2017.
• 5、 Verenikina et al.. "". . . Retrieved 1977.
• 6、 Adachi, Osao,Ano, Yoshitaka,Moonmangmee, Duangtip,Shinagawa, Emiko,Toyama, Hirohide,Theeragool, Gunjana,Lotong, Napha,Matsushita, Kazunobu. "Crystallization and properties of NADPH-dependent L-sorbose reductase from Gluconobacter melanogenus IFO 3294". . p. 2137 - 2143. Retrieved 1999.
• 7、 Kwon, Ji Soo,Kim, Ji Sun,Lee, Hak Sung,Lee, Man Sig. "Surface modification of SiO2 for highly dispersed Pd/SiO2 Catalyst". . p. 882 - 887. Retrieved 2019.
• 8、 Supeno, Minto,Nurhaidapasaribu,Siburian, Rikson. "Role OfTiO2 pillared bentonit and catalyst nickel for hydrogenation glucose to generate sorbitol". . p. 2819 - 2825. Retrieved 2018.
• 9、 Wei, Wei,Wang, Cong,Zhao, Yu,Peng, Shichao,Zhang, Haoyang,Bian, Yipeng,Li, Hexing,Zhou, Xinggui,Li, Hui. "Biochemical composite synthesized by stepwise crosslinking: An efficient platform for one-pot biomass conversion". . p. 78 - 85. Retrieved 2015.
• 10、 Dabbawala, Aasif A.,Mishra, Dinesh K.,Hwang, Jin-Soo. "Selective hydrogenation of D-glucose using amine functionalized nanoporous polymer supported Ru nanoparticles based catalyst". . p. 163 - 173. Retrieved 2016.