Carboxymethyl cellulose

Carboxymethyl cellulose

Names
Other names Carboxymethylcellulose; carmellose; E466
Identifiers
CAS Registry Number	9000-11-7 Y
ChEBI	CHEBI:85146 N
ChEMBL	ChEMBL1909054 N
ChemSpider	Y
Properties
Chemical formula	variable
Molar mass	variable
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

Carboxymethyl cellulose (CMC) or cellulose gum^[1] is a cellulose derivative with carboxymethyl groups (-CH₂-COOH) bound to some of the hydroxyl groups of the glucopyranose monomers that make up the cellulose backbone. It is often used as its sodium salt, sodium carboxymethyl cellulose.

Preparation

It is synthesized by the alkali-catalyzed reaction of cellulose with chloroacetic acid. The polar (organic acid) carboxyl groups render the cellulose soluble and chemically reactive.

The functional properties of CMC depend on the degree of substitution of the cellulose structure (i.e., how many of the hydroxyl groups have taken part in the substitution reaction), as well as the chain length of the cellulose backbone structure and the degree of clustering of the carboxymethyl substituents.

Uses

CMC is used in food under the E number E466 as a viscosity modifier or thickener, and to stabilize emulsions in various products including ice cream. It is also a constituent of many non-food products, such as toothpaste, laxatives, diet pills, water-based paints, detergents, textile sizing, and various paper products. It is used primarily because it has high viscosity, is nontoxic, and is generally considered to be hypoallergenic as the major source fiber is either softwood pulp or cotton linter.^[2][3] CMC is used extensively in gluten free ^[4] and reduced fat food products.^[5] In laundry detergents, it is used as a soil suspension polymer designed to deposit onto cotton and other cellulosic fabrics, creating a negatively charged barrier to soils in the wash solution. CMC is used as a lubricant in artificial tears. Sometimes methyl cellulose (MC) is used, but its nonpolar methyl groups (-CH₃) do not add any solubility or chemical reactivity to the base cellulose.

Following the initial reaction, the resultant mixture produces about 60% CMC plus 40% salts (sodium chloride and sodium glycolate). This product is the so-called technical CMC which is used in detergents. A further purification process is used to remove these salts to produce the pure CMC used for food, pharmaceutical, and dentifrice (toothpaste) applications. An intermediate "semipurified" grade is also produced, typically used in paper applications such as restoration of archival documents.

CMC is also used in pharmaceuticals as a thickening agent, and in the oil-drilling industry as an ingredient of drilling mud, where it acts as a viscosity modifier and water retention agent. Polyanionic cellulose (PAC) derived from cellulose is also used in oilfield practice. CMC is both chemically and physically distinguished from polyanionic cellulose. CMC is definitely a carboxylic acid, where PAC is an ether. Although CMC and PAC are manufactured from the same raw materials, by adjusting the type of cellulose and stoichiometry of the reactants, different final products may be produced. The primary difference between the CMC and PAC production processes is in the radicalization step.

Knitted fabric made of cellulose (eg cotton or viscose rayon) may be converted into CMC and used in various medical applications. 1 Device for epitaxis (nose bleeding). A pvc balloon is covered by CMC knitted fabric reinforced by nylon. The device is soaked in water to form a gel, this is inserted into the nose and the balloon inflated. The combination of the inflated balloon and the therapeutic effect of the cmc stops the bleeding. (see "Rapid Rhino") 2 Fabric used as a dressing following ENT surgical procedures. 3 Added water to form a gel. This gel is inserted into sinus cavity following surgery.

Insoluble microgranular CMC is used as a cation-exchange resin in ion-exchange chromatography for purification of proteins.^[6] Presumably, the level of derivatization is much lower, so the solubility properties of microgranular cellulose are retained, while adding sufficient negatively charged carboxylate groups to bind to positively charged proteins.

CMC is also used in ice packs to form a eutectic mixture resulting in a lower freezing point, and therefore more cooling capacity than ice.^[7]

Aqueous solutions of CMC have also been used to disperse carbon nanotubes. The long CMC molecules are thought to wrap around the nanotubes, allowing them to be dispersed in water. In conservation-restoration, it is used as an adhesive or fixative (commercial name Klucel).

CMC is used to achieve tartrate or cold stability in wine. This innovation may save megawatts of electricity used to chill wine in warm climates. It is more stable than metatartaric acid and is very effective in inhibiting tartrate precipitation. It is reported (Gerbaux 1996) that KHT crystals, in presence of CMC, grow slower and change their morphology. Their shape becomes flatter because they lose 2 of the 7 faces, changing their dimensions. CMC molecules, negatively charged at wine pH, interact with the electropositive surface of the crystals, where potassium ions are accumulated. The slower growth of the crystals and the modification of their shape are caused by the competition between CMC molecules and bitartrate ions for binding to the KHT crystals (Cracherau et al. 2001).

In veterinary medicine, CMC is used in abdominal surgeries in large animals, particularly horses, to prevent the formation of bowel adhesions.

Culinary Uses

CMC powder is widely used in ice cream industry. It is used to make ice creams without churning mechanism or extreme low temperatures thereby eliminating the need of the conventional churners or salt ice mixes.^[8]CMC is used in bakery products like breads and cake preparation. The use of CMC gives loaf a much improved quality at a reduced cost to the baker economizing on the fat component. CMC is also used as an emulsifier in producing high quality Biscuits. Due to CMC, fat disperses uniformly in the dough and hence CMC improves the release of the dough from the moulds and cutters to achieve well-shaped biscuits without any distorted edges. It can help to reduce consumption of egg yolk or fat used in making biscuits, thus achieving economy.Use of CMC. in the candy preparation, ensures smooth dispersion in flavour oils, improves texture & quality. They are used in chewing gums, margarines and peanut butter as emulsifier.^[9]

Enzymology

CMC has also been used extensively to characterize enzyme activity from endoglucanases (part of the cellulase complex). CMC is a highly specific substrate for endo-acting cellulases, as its structure has been engineered to decrystallize cellulose and create amorphous sites that are ideal for endoglucanase action. CMC is desirable because the catalysis product (glucose) is easily measured using a reducing sugar assay, such as 3,5-dinitrosalicylic acid. Using CMC in enzyme assays is especially important in regard to screening for cellulase enzymes that are needed for more efficient cellulosic ethanol conversion. However, CMC has also been misused in earlier work with cellulase enzymes, as many had associated whole cellulase activity with CMC hydrolysis. As the mechanism of cellulose depolymerization has become more understood, exocellulases are shown to be dominant in the degradation of crystalline (e.g. Avicel) and not soluble (e.g. CMC) cellulose.

See also

• Hydroxypropyl cellulose
• Methyl cellulose
• Croscarmellose sodium

References

External links

• CMC chemical structure and properties
• MC and CMC: commercial preparations and various uses, including paper conservation; bibliography