E 420

E 420 that occurs in rose hips and rowan berries. 
E 420 can be synthesized by the reduction of glucose. 
E 420 is used to make vitamin C (ascorbic acid) and surfactants. 

CAS:    50-70-4
MF:    C6H14O6
MW:    182.17
EINECS:    200-061-5

E 420 is also used in medicines and as a sweetener (particularly in foods for diabetics). 
E 420 is an isomer of mannitol.
A polyhydric alcohol, CH2OH(CHOH)4CH2OH, derived from glucose; E 420 is isomeric with mannitol. 
E 420 is found in rose hips and rowan berries and is manufactured by the catalytic reduction of glucose with hydrogen. 
E 420 is used as a sweetener (in diabetic foods) and in the manufacture of vitamin C and various cosmetics, foodstuffs, and medicines.

E 420 is a non-volatile polyhydric sugar alcohol. 
E 420 is chemically stable and not easily to be oxidized by air. 
E 420 is easily soluble in water, hot ethanol, methanol, isopropanol, butanol alcohol, cyclohexanol, phenol, acetone, acetic acid and dimethyl formamide. 
E 420 is widely distributed in nature plant fruit. 
E 420 is not easy to be fermented by various kinds of microorganism and have a excellent heat resistance without decomposing even at high temperature (200 °C). 
E 420 is initially separated from the mountain strawberry by the Boussingault (French) et al. The pH value of the saturated aqueous solution is 6 to 7. 

E 420 is isomer of mannitol, Taylor alcohol, and galactose alcohol. 
E 420 has a refreshing sweet taste with sweetness being 65% of sucrose. 
E 420 has excellent moisture absorption capability with a low calorific value and has very wide range of effects on the food, cosmetic, pharmaceutical field. 
When applied in food, E 420 can prevent the food drying, aging, and can extend the shelf life of products as well as effectively prevent the precipitation of sugars and salts contained in the foods and thus maintain the strength balance of sweetness, sour, bitter and enhance food flavor. 
E 420 can be synthesize from the hydrogenation of glucose under heating and high pressure with the existence of nickel catalyst.

E 420 is chemically relatively inert and is compatible with most excipients. 
E 420 is stable in air in the absence of catalysts and in cold, dilute acids and alkalis. 
E 420 does not darken or decompose at elevated temperatures or in the presence of amines. 
E 420 is nonflammable, noncorrosive, and nonvolatile.
Although E 420 is resistant to fermentation by many microorganisms, a preservative should be added to sorbitol solutions. 
E 420 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.

E 420 will form water-soluble chelates with many divalent and trivalent metal ions in strongly acidic and alkaline conditions. 
Addition of liquid polyethylene glycols to E 420, with vigorous agitation, produces a waxy, water-soluble gel with a melting point of 35–40℃. 
E 420 solutions also react with iron oxide to become discolored.
E 420 increases the degradation rate of penicillins in neutral and aqueous solutions.

E 420, also known as glucitol, occurs widely in plants, such as, the fruits of the Sorbus and Crataegus spp.  
Commercially E 420 is produced by the catalytic hydrogenation of glucose (Collins, 2006).  Sorbitol is approved as a sugar substitute with the E number 420 and has ‘generally recognized as safe’ status (GRAS) from the US Food and Drug Administration. 
E 420 is about 60% as sweet as sucrose and is a mild laxative.  

E 420 has a wide range of other functional properties, including: humectancy, plasticizing ability, non-cariogenicity, and good chemical stability in harsh conditions, such as, alkaline pH and heat. 
Toothpaste production is the second largest application of E 420, accounting for 50,000 tons a year in Western Europe alone.  
Other important uses of E 420 as a humectant, include: formulation of cough syrups, multivitamin preparations, emulsions, and suspensions (O’Neil, 2013).

E 420 can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alcohol group (−CH2OH). 
Most E 420 is made from potato starch, but it is also found in nature, for example in apples, pears, peaches, and prunes.
E 420 is converted to fructose by sorbitol-6-phosphate 2-dehydrogenase. 
E 420 is an isomer of mannitol, another sugar alcohol; the two differ only in the orientation of the hydroxyl group on carbon 2.
While similar, the two sugar alcohols have very different sources in nature, melting points, and uses.
As an over-the-counter drug, E 420 is used as a laxative to treat constipation.

E 420 Chemical Properties
Melting point: 98-100 °C (lit.)
Alpha: 4 º (per eur. pharm.)
Boiling point: 4bp760 105°
Density: 1.28 g/mL at 25 °C
Vapor density: <1 (vs air)
Vapor pressure: <0.1 mm Hg ( 25 °C)
Refractive index: n20/D 1.46
FEMA: 3029 | D-SORBITOL
Fp: >100°C
Storage temp.: room temp
Solubility: Very soluble in water, slightly soluble in ethanol
Form: liquid
pka: pKa (17.5°): 13.6
Color: White
Specific Gravity: 1.28
Odor: Odorless
PH Range: 5 - 7 at 182 g/l at 25 °C
PH: 5.0-7.0 (25℃, 1M in H2O)
optical activity: [α]20/D 1.5±0.3°, c = 10% in H2O
Water Solubility: SOLUBLE
Sensitive: Hygroscopic
λmax λ: 260 nm Amax: 0.04
λ: 280 nm Amax: 0.045
Merck: 14,8725
BRN: 1721899
Stability: Stable. Avoid strong oxidizing agents. Protect from moisture.
InChIKey: FBPFZTCFMRRESA-JGWLITMVSA-N
CAS DataBase Reference: 50-70-4(CAS DataBase Reference)
NIST Chemistry Reference: E 420(50-70-4)
EPA Substance Registry System: E 420 (50-70-4)

E 420 is white and odorless crystalline powder with sweet taste and being hygroscopic. 
E 420 can be dissolved in water (235g/100g water, 25 °C), glycerin, and propylene glycol; and is slightly soluble in methanol, ethanol, acetic acid, and phenol and acetamide solution but almost insoluble in most other organic solvents.
E 420 is D-glucitol. 

E 420 is a hexahydric alcohol related to mannose and is isomeric with mannitol.
E 420 occurs as an odorless, white or almost colorless, crystalline, hygroscopic powder. 
Four crystalline polymorphs and one amorphous form of E 420 have been identified that have slightly different physical properties, e.g. melting point. 
E 420 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. 
E 420 has a pleasant, cooling, sweet taste and has approximately 50–60% of the sweetness of sucrose.

Uses    

1. Daily chemical industry
E 420 can be used as an excipient, moisturizing agents, and antifreeze agents in toothpaste, with the added amount being up to 25 to 30%. 
E 420 can help maintain the lubrication, color, and good taste for the paste. 
In cosmetics field, E 420 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 E 420's 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 E 420 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 E 420 is lower than that of sucrose, and can’t be exploited by any bacteria. 
E 420 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, E 420 can also be applied as a sweetener agent and nutrient agent for the food of patients with diabetes.
E 420 does not contain an aldehyde group and is not easily oxidized.

E 420 will not have Maillard reaction with amino acids upon heating. 
E 420 also has certain physiological activity. 
E 420 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
E 420 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.

Laxative
As is the case with other sugar alcohols, foods containing E 420 can cause gastrointestinal distress. 
E 420 can be used as a laxative when taken orally or as an enema.
E 420 works as a laxative by drawing water into the large intestine, stimulating bowel movements.
E 420 has been determined safe for use by the elderly, although it is not recommended without the advice of a physician.

E 420 is commonly used orally as a one-time dose of 30–150 millilitres (1.1–5.3 imp fl oz; 1.0–5.1 US fl oz) 70% solution.
E 420 may also be used as a one-time rectal enema.

Other medical applications
E 420 is used in bacterial culture media to distinguish the pathogenic Escherichia coli O157:H7 from most other strains of E. coli, because it is usually unable to ferment sorbitol, unlike 93% of known E. coli strains.

A treatment for hyperkalaemia (elevated blood potassium) uses E 420 and the ion-exchange resin sodium polystyrene sulfonate (tradename Kayexalate).
The resin exchanges sodium ions for potassium ions in the bowel, while E 420 helps to eliminate it. 
In 2010, the U.S. FDA issued a warning of increased risk for gastrointestinal necrosis with this combination.
E 420 is also used in the manufacture of softgel capsules to store single doses of liquid medicines.

Health care, food, and cosmetic uses
E 420 often is used in modern cosmetics as a humectant and thickener.
E 420 is also used in mouthwash and toothpaste. 
Some transparent gels can be made only with E 420, because of its high refractive index.

E 420 is used as a cryoprotectant additive (mixed with sucrose and sodium polyphosphates) in the manufacture of surimi, a processed fish paste.
E 420 is also used as a humectant in some cigarettes.

Beyond its use as a sugar substitute in reduced-sugar foods, E 420 is also used as a humectant in cookies and low-moisture foods like peanut butter and fruit preserves. 
In baking, E 420 is also valuable because it acts as a plasticizer, and slows down the staling process.

Miscellaneous uses
A mixture of E 420 and potassium nitrate has found some success as an amateur solid rocket fuel.

E 420 is identified as a potential key chemical intermediate for production of fuels from biomass resources. 
Carbohydrate fractions in biomass such as cellulose undergo sequential hydrolysis and hydrogenation in the presence of metal catalysts to produce E 420.
Complete reduction of E 420 opens the way to alkanes, such as hexane, which can be used as a biofuel. 
Hydrogen required for this reaction can be produced by aqueous phase catalytic reforming of E 420.

19 C6H14O6 → 13 C6H14 + 36 CO2 + 42 H2O
The above chemical reaction is exothermic, and 1.5 moles of E 420 generate approximately 1 mole of hexane. 
When hydrogen is co-fed, no carbon dioxide is produced.

E 420 based polyols are used in the production of polyurethane foam for the construction industry.
E 420 is also added after electroporation of yeasts in transformation protocols, allowing the cells to recover by raising the osmolarity of the medium.

4. the chemical industry
E 420 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.
E 420 can from complex with iron, copper, and aluminum ion in alkaline solution to be applied to the washing and bleaching in textile industry.
Using E 420 and propylene oxide as a starting material can produce rigid polyurethane foam as well as have some flame retardant properties.

E 420 is a sugar alcohol that is naturally found in Toyon berries. 
E 420 is used to increase stability of silver nanoparticles and is also used as a sugar substitute.
E 420 is a humectant that is a polyol (polyhydric alcohol) produced by hydrogenation of glucose with good solubility in water and poor solubility in oil. 
E 420 is approximately 60% as sweet as sugar, and has a caloric value of 2.6 kcal/g. 
E 420 is highly hygroscopic and has a pleasant, sweet taste. 
E 420 maintains moistness in shredded coconut, pet foods, and candy. 
In sugarless frozen desserts, E 420 depresses the freezing point, adds solids, and contributes some sweetness. 

E 420 is used in low-calorie beverages to provide body and taste. 
E 420 is used in dietary foods such as sugarless candy, chewing gum, and ice cream. 
E 420 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. 
E 420 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).

E 420 is widely used as an excipient in pharmaceutical formulations. 
E 420 is also used extensively in cosmetics and food products.
E 420 is used as a diluent in tablet formulations prepared by either wet granulation or direct compression. 
E 420 is particularly useful in chewable tablets owing to its pleasant, sweet taste and cooling sensation. 
In capsule formulations E 420 is used as a plasticizer for gelatin. 
E 420 has been used as a plasticizer in film formulations.

In liquid preparations E 420 is used as a vehicle in sugar-free formulations and as a stabilizer for drug, vitamin, and antacid suspensions. 
Furthermore, E 420 is used as an excipient in liquid parenteral biologic formulations to provide effective protein stabilization in the liquid state. 
E 420 has also been shown to be a suitable carrier to enhance the in vitro dissolution rate of indometacin. 
In syrups E 420 is effective in preventing crystallization around the cap of bottles. 
E 420 is additionally used in injectable and topical preparations, and therapeutically as an osmotic laxative.
E 420 may also be used analytically as a marker for assessing liver blood flow.

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. E 420 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 E 420 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 E 420 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%.

Manufacturing Process    
20 ml of a suspension of CTAB-permeabilized cells of Zymomonas mobilis were mixed with 80 ml of a 4% carrageenan solution and the mixture was poured into shallow dishes and allowed to rigidify. 
The rigidified immobilizate was then divided into 3x3x3 mm cubes, exposed to a solution of 0.3 M KCl overnight and then divided into batches and exposed to one of the following treatments:

(A) Cubes stabilized with potassium ions were used without further treatment for production of sorbitol/gluconic acid.

(B) Cubes were incubated with a 1.0% solution of polyethyleneimine at room temperature for 30 min and then treated with glutaraldehyde at 4°C for 30 min.

Comparison of two rigidification methods:
A volume of 450 ml of cubes treated by the method described in (A) were reacted in a 1.5 liter fluidized bed fermenter with a substrate solution comprised of 100 g/L glucose, 100 g/L fructose and a protein concentration of 6.1 g/L, at a D of 0.053 h-1, and titrated with 3 N KOH. 
After 48 hours, 68.8% of the substrate was converted with a resulting production of 3.65 g sorbitol/L*h and 0.6 g sorbitol/g protein*h. 
After approximately 50 days, the productivity of the fermenter was reduced by about one half.

Cubes treated as described (B) using glutaraldehyde at a concentration of 0.5%, were reacted in a 1.6 liter fermenter with a substrate solution comprised of 100 g/L glucose, 100 g/L fructose and a protein concentration of 8.6 g/L, at a D of 0.055 h-1, and titrated with 3 N KOH. 
After 48 hours, 90.0% of the substrate was converted with a resulting production of 4.95 g sorbitol/L*h and 0 58 g sorbitol/g protein*h. 
After 75 days, the productivity of the fermenter was reduced by only 3.5%.

Reactivity Profile    
E 420 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.

Synonyms
D-Sorbitol
sorbitol
D-Glucitol
50-70-4
glucitol
L-Gulitol
(-)-Sorbitol
Glucarine
Diakarmon
Multitol
Sorbilande
Sorbostyl
D-(-)-Sorbitol
Esasorb
Neosorb
Nivitin
Siosan
Sorbite
Sorbol
Cholaxine
Sionit
Sionite
Sionon
Sorbo
Karion instant
Sorbitol F
Sorbex Rp
Sorbitol FP
D-Sorbol
Sionit K
Sorbex M
Sorbex R
Sorbex S
Sorbex X
Hexahydric alcohol
Sorbicolan
Sorvilande
Gulitol
(2R,3R,4R,5S)-Hexane-1,2,3,4,5,6-hexaol
Neosorb P 60
D-Sorbite
Foodol D 70
Neosorb 20/60DC
Neosorb 70/02
Neosorb 70/70
Glucitol, D-
Neosorb P 20/60
Karion
d-Sorbit
Karion (carbohydrate)
(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol
FEMA No. 3029
Probilagol
D-1,2,3,4,5,6-Hexanehexol
CCRIS 1898
G-ol
Neosorb P 60W
AI3-19424
HSDB 801
iso-sorbide
Glc-ol
NSC 25944
Sorbitol (e420)
CHEBI:17924
Ins no.420(i)
Ins-420(i)
Resulax
Sorbilax
1,2,3,4,5,6-Hexanehexol
E 420
E-420(i)
NSC-25944
506T60A25R
7B5697N
D-Sorbit 1000 microg/mL in Methanol
E420
Medevac
DSSTox_CID_3588
DSSTox_RID_77095
DSSTox_GSID_23588
Sorbitur
(2S,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol
26566-34-7
Sorbit DP
CAS-50-70-4
123236-29-3
SMR000112219
Sorbitol [USP:NF]
Sorbitol 3% in plastic container
WURCS=2.0/1,1,0/[h2122h]/1/
EINECS 200-061-5
MFCD00004708
Solbitol
SORBITOL 3.3% IN PLASTIC CONTAINER
Sorbitol S
DTXSID5023588
Sorbitol FK
UNII-506T60A25R
Sorbit D-Powder
Sorbit S
Sorbit W-Powder
Sorbit WP
Sorbitol (NF)
Neosorb P60
Kyowa Powder 50M
Sorbogem 712
Sorbitol (Glucitol)
Sorbit D 70
Sorbit DP 50
Sorbit L 70
Sorbit T 70
Sorbit W 70
D-Sorbitol, 99%
Sorbit W-Powder 50
D-[2-2H]Glucitol
D-sorbitol; D-glucitol
D-Sorbitol (JP17)
SORBITOL [HSDB]
SORBITOL [INCI]
SORBITOL [FCC]
SORBITOL [USP]
SORBITOL [II]
SORBITOL [MI]
SORBITOL [VANDF]
D-Sorbitol, >=98%
D-SORBITOL [JAN]
SCHEMBL763
Sorbit Kyowa Powder 50M
SORBITOL [MART.]
bmse000115
bmse000803
bmse001007
D-SORBITOL [FHFI]
Epitope ID:114708
SORBITOL [USP-RS]
SORBITOL [WHO-DD]
Isomalt impurity, sorbitol-
D-Sorbitol, NF/FCC grade
CHEMBL1682
MLS001333209
MLS001333210
SORBITOL [ORANGE BOOK]
D-Sorbitol, analytical standard
D-Sorbitol, for electrophoresis
SORBITOL [EP MONOGRAPH]
D-Sorbitol, BioXtra, >=98%
D-Sorbitol, for synthesis, 99%
HMS2094K21
HMS2270A18
Pharmakon1600-01300028
HY-B0400
Tox21_201937
Tox21_303388
D-Sorbitol, >=98%, FCC, FG
NSC759608
s2393
ZINC18279893
AKOS015899604
D-Sorbitol, plant cell culture tested
CCG-229392
DB01638
NSC-759608
Sorbitol 3% in plastic container (TN)
ISOMALT IMPURITY C [EP IMPURITY]
NCGC00164353-01
NCGC00164353-02
NCGC00164353-03
NCGC00257447-01
NCGC00259486-01
AC-13186
CS-13177
MALTITOL IMPURITY A [EP IMPURITY]
D-Sorbitol, SAJ first grade, >=97.0%
SBI-0206688.P002
SORBITOL-MANNITOL COMPONENT SORBITOL
D-Sorbitol, for molecular biology, >=98%
D-Sorbitol, BioUltra, >=99.5% (HPLC)
D-Sorbitol, SAJ special grade, >=99.0%
D-Sorbitol, Vetec(TM) reagent grade, 97%
E-420
S0065
SW220289-1
D-Sorbitol, crystallized, >=99.0% (HPLC)
SORBITOL COMPONENT OF SORBITOL-MANNITOL
A15606
C00794
D00096
E70384
AB00919085_06
D-Sorbitol, liquid, tested according to Ph.Eur.
EN300-7832133
ISOMALT IMPURITY, SORBITOL- [USP IMPURITY]
Q245280
5-(4-Methoxyphenyl)-1,3-Oxazole-4-CarboxylicAcid
LACTITOL MONOHYDRATE IMPURITY E [EP IMPURITY]
Sorbitol, European Pharmacopoeia (EP) Reference Standard
75DE42C3-7C3B-4802-95E0-463F02268BDC
Sorbitol, United States Pharmacopeia (USP) Reference Standard
D-Sorbitol, BioReagent, cell culture tested, plant cell culture tested
Sorbitol, Pharmaceutical Secondary Standard; Certified Reference Material