PRODUCTS

E466 (CARBOXYMETHYLCELLULOSE)

CAS Number: 9000-11-7
European Community (EC) Number: 618-378-6
IUPAC Name:
sodium;2,3,4,5,6-pentahydroxyhexanal;acetate
Molecular Formula: C8H15NaO8

DESCRIPTION:
E466 (Carboxymethylcellulose) (CMC) or cellulose gum 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.
E466 (Carboxymethylcellulose) is often used as its sodium salt, sodium E466 (Carboxymethylcellulose).
E466 (Carboxymethylcellulose) is used to be marketed under the name Tylose, a registered trademark of SE Tylose.
Preparation of E466 (Carboxymethylcellulose):
E466 (Carboxymethylcellulose) 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.

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

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.
E466 (Carboxymethylcellulose) is low viscosity cellulose gum
E466 (Carboxymethylcellulose) is superior water retention properties for baking applications
E466 (Carboxymethylcellulose)controls texture and ice crystal growth in frozen dairy products
E466 (Carboxymethylcellulose) improves moisture retention in low calorie foods
E466 (Carboxymethylcellulose) is cold/hot soluble, non-gelling

E466 (Carboxymethylcellulose) (CMC), also known as cellulose gum or Tylose, and its sodium salt are important cellulose derivatives.
The bound carboxymethyl groups (-CH2-COOH) along the polymer chain makes the cellulose water-soluble.
When dissolved, E466 (Carboxymethylcellulose) increases the viscosity of aqueous solutions, suspensions and emulsions, and at higher concentration, E466 (Carboxymethylcellulose) provides pseudo-plasticity or thixotropy.
As a natural polyelectrolyte, CMC imparts a surface charge to neutral particles and thus, can be used to improve the stability of aqueous colloids and gels or to induce agglomeration.

E466 (Carboxymethylcellulose) or CMC is a water soluble salt.
E466 (Carboxymethylcellulose) belongs to the family of the polymers produced by etherification of native cellulose by substituting hydroxyl groups of carboxymethyl groups in the cellulose chain.
Being dissolved in hot or cold water, the CMC can be produced with different physical and chemical properties.
These properties can affect the behavior of the product in its various applications, as well as being essential for optimizing production costs.
E466 (Carboxymethylcellulose) is a non-toxic product

Carboxymethylcellulose is a cellulose derivative that consists of the cellulose backbone made up of glucopyranose monomers and their hydroxyl groups bound to carboxymethyl groups.
Carboxymethylcellulose is added in food products as a viscosity modifier or thickener and emulsifier.
Carboxymethylcellulose is also one of the most common viscous polymers used in artificial tears, and has shown to be effective in the treatment of aqueous tear-deficient dry eye symptoms and ocular surface staining.
The viscous and mucoadhesive properties as well as its anionic charge allow prolonged retention time in the ocular surface.
Sodium carboxymethylcellulose is the most commonly used salt.

CAS Number: 9000-11-7
European Community (EC) Number: 618-378-6
IUPAC Name: sodium;2,3,4,5,6-pentahydroxyhexanal;acetate
Molecular Formula: C8H15NaO8

Mechanism of action:

Carboxymethylcellulose binds to the surface of corneal epithelial cells via its glucopyranose subunits binding to glucose receptors GLUT-1 .
The residence time of carboxymethylcellulose bound to corneal cells is approximately 2 hours as indicated by a short-term binding assay
Binding of carboxymethylcellulose to the matrix proteins stimulated corneal epithelial cell attachment, migration, and re-epithelialization of corneal wounds.

Pharmacodynamics:
In a randomized clinical study of patients with mild or moderate forms of eye dryness, ophthalmic treatment with sodium carboxymethylcellulose resulted in a diminished frequency of symptoms compared to the placebo group.
Carboxymethylcellulose interacts with human corneal epithelial cells to facilitate corneal epithelial wound healing and attenuate eye irritation in a dose-dependent manner.
It exhibits protective actions on the ocular surface in various applications; it mediates cytoprotective effects on the ocular surface when applied prior to contact lenses and reduces the incidence of epithelial defects during LASIK

Uses of E466 (Carboxymethylcellulose):

CMC is used in food under the E number E466 or E469 (when it is enzymatically hydrolyzed) as a viscosity modifier or thickener, and to stabilize emulsions in various products including ice cream.
E466 (Carboxymethylcellulose) is also a constituent of many non-food products, such as toothpaste, laxatives, diet pills, water-based paints, detergents, textile sizing, reusable heat packs, various paper products, and also in leather crafting to help burnish the edges.
E466 (Carboxymethylcellulose) 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.
CMC is used extensively in gluten free and reduced fat food products.
In laundry detergents, E466 (Carboxymethylcellulose) 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.
In ophthalmology, CMC is used as a lubricant in artificial tears to treat dry eyes.
Extensive treatment may be required to treat severe dry eye syndrome or Meibomian gland dysfunction (MGD).

CMC is also used as a thickening agent, for example, in the oil-drilling industry as an ingredient of drilling mud, where it acts as a viscosity modifier and water retention agent.
Sodium CMC(Na CMC) for example, is used as a negative control agent for alopecia in rabbits.

Knitted fabric made of cellulose (e.g. cotton or viscose rayon) may be converted into CMC and used in various medical applications.
A poly-vinyl chloride (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.
Fabric used as a dressing following ear nose and throat surgical procedures.
Water is added to form a gel, and this gel is inserted into the sinus cavity following surgery.
Insoluble microgranular CMC is used as a cation-exchange resin in ion-exchange chromatography for purification of proteins.
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.

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 Walocel, 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 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

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

CMC is sometimes used as an electrode binder in advanced battery applications (i.e. lithium ion batteries), especially with graphite anodes.
CMC's water solubility allows for less toxic and costly processing than with non-water-soluble binders, like the traditional polyvinylidene fluoride (PVDF), which requires toxic n-methylpyrrolidone (NMP) for processing.
CMC is often used in conjunction with styrene-butadiene rubber (SBR) for electrodes requiring extra flexibility, e.g. for use with silicon-containing anodes.
E466 (Carboxymethylcellulose) is used in drilling muds, detergents, resin emulsion paints, adhesives, printing inks, and textile sizes.
E466 (Carboxymethylcellulose) is also used as a protective colloid, a stabilizer for foods, and a pharmaceutical additive.
E466 (Carboxymethylcellulose) is used as a bulk laxative, emulsifier and thickener in cosmetics and pharmaceuticals, and stabilizer for reagents.
E466 (Carboxymethylcellulose) formerly registered in the US for use as an insecticide for ornamentals and flowering plants .
Permitted for use as an inert ingredient in non-food pesticide products .
E466 (Carboxymethylcellulose) is used as an anticaking agent, drying agent, emulsifier, formulation aid, humectant, stabilizer or thickener, and texturizer in foods.

E466 (Carboxymethylcellulose) is used as an additive in industry that enables different applications:
•    Thickener
•    Stabilizing
•    Filled
•    Dietary fiber
•    Emulsifier
Other applications can be performed in the following fields:
Construction: E466 (Carboxymethylcellulose) is used in cement compositions acting as a stabilizer and hydrophilic agent.
Detergents: E466 (Carboxymethylcellulose) is used for soaps and detergents acting as an inhibitor of fat redeposition on fabrics after being eliminated by the detergent.
Paper: E466 (Carboxymethylcellulose) reduces consumption of wax paper wax having lower penetration of wax paper cartons.
Agriculture: E466 (Carboxymethylcellulose) is suspending agent in pesticides and water-based sprays.
Also E466 (Carboxymethylcellulose) is used as an aid in the degradation of some highly polluting fertilizers.
Adhesives: E466 (Carboxymethylcellulose) is additive in glues and adhesives.
Cosmetics: E466 (Carboxymethylcellulose) is used for dental impression materials and pastes or gels toothpaste.
Water-based paints: E466 (Carboxymethylcellulose) is used as thickener and suspending of the pigments in the fluid.
Oil: In drilling muds to avoid ground settlement.
Plastic: plastic viscosity increases as latex.
Ceramics: E466 (Carboxymethylcellulose) is used to join pieces of porcelain.
Textile: antideformate Agent fabrics.
Pharmaceutical industry: E466 (Carboxymethylcellulose) is used as forming gels, stabilizer for suspensions, emulsions, sprays and bioadhesive.
Food: E466 (Carboxymethylcellulose) is assistant in the batter ice cream, cream and cream; as an auxiliary to form gels in gelatins and puddings; dressings and fillings thickener, suspending agent in fruit juices, etc.
Medicine: E466 (Carboxymethylcellulose) is used in formation of gels in heart surgeries, thoracic and cornea.

CAS Number: 9000-11-7
European Community (EC) Number: 618-378-6
IUPAC Name:
sodium;2,3,4,5,6-pentahydroxyhexanal;acetate
Molecular Formula: C8H15NaO8

Culinary uses of E466 (Carboxymethylcellulose):
CMC powder is widely used in the ice cream industry, to make ice creams without churning or extremely low temperatures, thereby eliminating the need for the conventional churners or salt ice mixes.
CMC is used in baking breads and cakes.
The use of CMC gives the loaf an improved quality at a reduced cost, by reducing the need of fat. CMC is also used as an emulsifier in high quality biscuits.
By dispersing fat uniformly in the dough, E466 (Carboxymethylcellulose) improves the release of the dough from the moulds and cutters, achieving well-shaped biscuits without any distorted edges.
E466 (Carboxymethylcellulose) can also help to reduce the amount of egg yolk or fat used in making the biscuits.
Use of CMC in candy preparation ensures smooth dispersion in flavour oils, and improves texture and quality.
CMC is used in chewing gums, margarines and peanut butter as an emulsifier.

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 better understood, exo-cellulases are dominant in the degradation of crystalline (e.g. Avicel) and not soluble (e.g. CMC) cellulose.

Sodium E466 (Carboxymethylcellulose) (CMC) is used in many products including adhesives, sealants, coatings, textiles, ceramics, mining products, building and construction materials, laundry detergents, pulp, paper, and tobacco.
E466 (Carboxymethylcellulose) functions as a dispersant agent, emulsifier, stabilizer, water retainer, thickener and clarifying agent.
E466 (Carboxymethylcellulose) is used as a film-forming and binding agent, for example to agglomerate and bind iron ore into pellets.
Since CMC is physiologically harmless, E466 (Carboxymethylcellulose) is also widely used in the food, cosmetic, and pharmaceutical industries.
In food products, E466 (Carboxymethylcellulose) acts as a thickener, stabilizer and binder and helps to control crystallization, moisture retention, and fat uptake.
In cosmetic products such as creams and lotions, E466 (Carboxymethylcellulose) thickens and stabilizes the product and improves its moisturising effect.
And in tooth pastes E466 (Carboxymethylcellulose) is added to adjust the viscosity profile

Carboxymethylcellulose (CMC) is a thickening agent that is made by reacting CELLULOSE (wood pulp, cotton lint) with a derivative of acetic acid (the acid in vinegar).
Carboxymethylcellulose is also called cellulose gum.

CMC has long been considered safe, but a 2015 study funded by the National Institutes of Health raised some doubts.
It found that both CMC and another emulsifier (polysorbate 80) affected gut bacteria and triggered inflammatory bowel disease symptoms and other changes in the gut, as well as obesity and a set of obesity-related disease risk factors known as metabolic syndrome.
In mice that were predisposed to colitis, the emulsifiers promoted the disease.
It is possible that polysorbates, CMC, and other emulsifiers act like detergents to disrupt the mucous layer that lines the gut, and that the results of the study may apply to other emulsifiers as well. Research is needed to determine long-term effects of these and other emulsifiers at levels that people consume.

CMC is not absorbed or digested, so the FDA allows it to be included with “dietary fiber” on food labels.
CMC isn’t as healthful as fiber that comes from natural foods.

CAS Number: 9000-11-7
European Community (EC) Number: 618-378-6
IUPAC Name:
sodium;2,3,4,5,6-pentahydroxyhexanal;acetate
Molecular Formula: C8H15NaO8

Chemical and Physical Properties of E466 (Carboxymethylcellulose):

Molecular Weight:    262.19
Hydrogen Bond Donor Count:    5
Hydrogen Bond Acceptor Count:    8
Rotatable Bond Count:    5
Exact Mass:    262.06646171
Monoisotopic Mass:    262.06646171
Topological Polar Surface Area:    158 Å²
Heavy Atom Count:    17
Formal Charge:    0
Complexity:    173
Isotope Atom Count:    0
Defined Atom Stereocenter Count:    0
Undefined Atom Stereocenter Count:    4
Defined Bond Stereocenter Count:    0
Undefined Bond Stereocenter Count:    0
Covalently-Bonded Unit Count:    3
Compound Is Canonicalized:    Yes
Physical State :Solid
Solubility :Soluble in water (20 mg/ml).
Storage :Store at room temperature
Physical Description:
•    White solid
•    Powdered form is hygroscopic
•    White or slightly yellowish hygroscopic solid
•    Nearly odorless
•    Beige hygroscopic powder

Chemical Classes:
Biological Agents -> Polysaccharides

Specifications of E466 (Carboxymethylcellulose):
Thanks to its versatility, the CMC can be used for various functions, which facilitate the use by different industries. Its most prominent features are:
•    Solubility
•    Rheology
•    Adsorption Surfaces
These main properties facilitate the CMC to control different properties of aqueous systems stabilizing effects such as water retention, thixotropic or training films.

There are different parameters that define the properties of the CMC:
Purity (content of active CMC): the CMC is produced with sodium purity giving the product.
Viscosity: one of the most interesting features of the CMC which can vary from low to high.
It is measured by digital viscometers in certain temperatures and in different dissolution percentages (1%, 2% or 4%).
Degree of substitution: is the average number of sodium carboxymethyl groups per anhydroglucose unit in the cellulose structure.
This parameter is important in various areas of product application.
Physical form: CMC can produce powder or granular.

CAS Number: 9000-11-7
European Community (EC) Number: 618-378-6
IUPAC Name:
sodium;2,3,4,5,6-pentahydroxyhexanal;acetate
Molecular Formula: C8H15NaO8

Synonyms:

Depositor-Supplied Synonyms:
9004-32-4

SODIUM E466 (Carboxymethylcellulose)

Cellulose gum

E466 (Carboxymethylcellulose), sodium salt

sodium;2,3,4,5,6-pentahydroxyhexanal;acetate

Carboxymethylcellulose sodium (USP)

Carboxymethylcellulose cellulose carboxymethyl ether

CMC powder

Celluvisc (TN)

C8H15NaO8

Carmellose sodium (JP17)

CHEMBL242021

C.M.C. (TN)

CHEBI:31357

E466

K625

D01544

E466 (Carboxymethylcellulose) sodium - Viscosity 100 - 300 mPa.s