Sorbitan monostearate

Last updated

Sorbitan monostearate
Sorbitan monostearate.svg
Names
Preferred IUPAC name
(2R)-2-[(2R,3R,4S)-3,4-Dihydroxyoxolan-2-yl]-2-hydroxyethyl octadecanoate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.014.241 OOjs UI icon edit-ltr-progressive.svg
E number E491 (thickeners, ...)
PubChem CID
UNII
  • InChI=1S/C24H46O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(27)29-19-21(26)24-23(28)20(25)18-30-24/h20-21,23-26,28H,2-19H2,1H3/t20-,21+,23+,24+/m0/s1 Yes check.svgY
    Key: HVUMOYIDDBPOLL-XWVZOOPGSA-N Yes check.svgY
  • InChI=1/C24H46O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(27)29-19-21(26)24-23(28)20(25)18-30-24/h20-21,23-26,28H,2-19H2,1H3/t20-,21+,23+,24+/m0/s1
    Key: HVUMOYIDDBPOLL-XWVZOOPGBK
  • O[C@H](COC(=O)CCCCCCCCCCCCCCCCC)[C@H]1OC[C@H](O)[C@H]1O
Properties
C24H46O6
Molar mass 430.62 g/mol
AppearanceWaxy powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)
Infobox references

Sorbitan monostearate is an ester of sorbitan (a sorbitol derivative) and stearic acid and is sometimes referred to as a synthetic wax. [1]

Contents

Uses

Sorbitan monostearate is used in the manufacture of food and healthcare products as a non-ionic surfactant with emulsifying, dispersing, and wetting properties.[ citation needed ] It is also employed to create synthetic fibers, metal machining fluid, and as a brightener in the leather industry. Sorbitans are also known as "Spans".

Sorbitan monostearate has been approved by the European Union for use as a food additive (emulsifier) (E number: E 491). [2] It is also approved for use by the British Pharmacopoeia. [3]

See also

Related Research Articles

Food additive Substances added to food

Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt, (salting), smoke (smoking), sugar (crystallization), etc. This allows for longer-lasting foods such as bacon, sweets or wines. With the advent of processed foods in the second half of the twentieth century, many additives have been introduced, of both natural and artificial origin. Food additives also include substances that may be introduced to food indirectly in the manufacturing process, through packaging, or during storage or transport.

E number Codes for food additives

E numbers are codes for substances used as food additives for use within the European Union (EU) and European Free Trade Association (EFTA). Commonly found on food labels, their safety assessment and approval are the responsibility of the European Food Safety Authority (EFSA).

Sorbitol Chemical compound

Sorbitol, less commonly known as glucitol, is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alcohol group (−CH2OH). Most sorbitol is made from potato starch, but it is also found in nature, for example in apples, pears, peaches, and prunes. It is converted to fructose by sorbitol-6-phosphate 2-dehydrogenase. Sorbitol 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.

Surfactant Substance that lowers the surface tension between a liquid and another material

Surfactants are compounds that lower the surface tension between two liquids, between a gas and a liquid, or between a liquid and a solid. Surfactants may act as detergents, wetting agents, emulsifiers, foaming agents, or dispersants.

Food coloring Dye, pigment, or substance that imparts color when it is added to food or drink

Food coloring, or color additive, is any dye, pigment, or substance that imparts color when it is added to food or drink. They come in many forms consisting of liquids, powders, gels, and pastes. Food coloring is used in both commercial food production and domestic cooking. Food colorants are also used in a variety of non-food applications, including cosmetics, pharmaceuticals, home craft projects, and medical devices.

Sodium stearoyl-2-lactylate is a versatile, FDA approved food additive used to improve the mix tolerance and volume of processed foods. It is one type of a commercially available lactylate. SSL is non-toxic, biodegradable, and typically manufactured using biorenewable feedstocks. Because SSL is a safe and highly effective food additive, it is used in a wide variety of products ranging from baked goods and desserts to pet foods.

Lecithin A generic term for amphiphilic substances of plant and animal origin

Lecithin is a generic term to designate any group of yellow-brownish fatty substances occurring in animal and plant tissues which are amphiphilic – they attract both water and fatty substances, and are used for smoothing food textures, emulsifying, homogenizing liquid mixtures, and repelling sticking materials.

Sodium benzoate Chemical compound

Sodium benzoate is a substance which has the chemical formula C6H5COONa. It is a widely used food pickling agent, with an E number of E211. It is the sodium salt of benzoic acid and exists in this form when dissolved in water. It can be produced by reacting sodium hydroxide with benzoic acid.

Polysorbate

Polysorbates are a class of emulsifiers used in some pharmaceuticals and food preparation. They are often used in cosmetics to solubilize essential oils into water-based products. Polysorbates are oily liquids derived from ethoxylated sorbitan esterified with fatty acids. Common brand names for polysorbates include Kolliphor, Scattics, Alkest, Canarcel, and Tween.

Monoglyceride

Monoglycerides are a class of glycerides which are composed of a molecule of glycerol linked to a fatty acid via an ester bond. As glycerol contains both primary and secondary alcohol groups two different types of monoglycerides may be formed; 1-monoacylglycerols where the fatty acid is attached to a primary alcohol, or a 2-monoacylglycerols where the fatty acid is attached to the secondary alcohol.

Polysorbate 20 is a polysorbate-type nonionic surfactant formed by the ethoxylation of sorbitan before the addition of lauric acid. Its stability and relative nontoxicity allows it to be used as a detergent and emulsifier in a number of domestic, scientific, and pharmacological applications. As the name implies the ethoxylation process leaves the molecule with 20 repeat units of polyethylene glycol; in practice these are distributed across 4 different chains, leading to a commercial product containing a range of chemical species.

Benzethonium chloride Chemical compound

Benzethonium chloride, also known as hyamine is a synthetic quaternary ammonium salt. This compound is an odorless white solid, soluble in water. It has surfactant, antiseptic, and anti-infective properties, and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in cosmetics and toiletries such as soap, mouthwashes, anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride is also used in the food industry as a hard surface disinfectant.

Sorbitan Chemical compound

Sorbitan is a mixture of isomeric organic compounds derived from the dehydration of sorbitol and is an intermediate in the conversion of sorbitol to isosorbide. Sorbitan is primarily used in the production of surfactants such as polysorbates; which are important emulsifying agents, with a total annual demand of more than 10000 tons in 2012.

Sorbitan tristearate Chemical compound

Sorbitan tristearate is a nonionic surfactant. It is variously used as a dispersing agent, emulsifier, and stabilizer, in food and in aerosol sprays. As a food additive, it has the E number E492. Brand names for polysorbates include Alkest, Canarcel, and Span. The consistency of sorbitan tristearate is waxy; its color is light cream to tan.

Dough conditioner

A dough conditioner, flour treatment agent, improving agent or bread improver is any ingredient or chemical added to bread dough to strengthen its texture or otherwise improve it in some way. Dough conditioners may include enzymes, yeast nutrients, mineral salts, oxidants and reductants, bleaching agents and emulsifiers. They are food additives combined with flour to improve baking functionality. Flour treatment agents are used to increase the speed of dough rising and to improve the strength and workability of the dough. While they are an important component of modern factory baking, some small-scale bakers reject them in favour of longer fermentation periods that produce greater depth of flavour.

Glycerol monostearate, commonly known as GMS, is a monoglyceride commonly used as an emulsifier in foods. It takes the form of a white, odorless, and sweet-tasting flaky powder that is hygroscopic. Chemically it is the glycerol ester of stearic acid.

Lactylates are organic compounds that are FDA approved for use as food additives and cosmetic ingredients. These additives are non-toxic, biodegradable, and typically manufactured using biorenewable feedstocks. Owing to their safety and versatile functionality, lactylates are used in a wide variety of food and non-food applications. In the United States, the Food Chemicals Codex specifies the labeling requirements for food ingredients including lactylates. In the European Union, lactylates must be labelled in accordance with the requirements of the applicable EU regulation. Lactylates may be labelled as calcium stearoyl lactylate (CSL), sodium stearoyl lactylate (SSL), or lactylic esters of fatty acids (LEFA).

Sorbitan monolaurate is a mixture of esters formed from the fatty acid lauric acid and polyols derived from sorbitol, including sorbitan and isosorbide. As a food additive, it is designated with the E number E493.

Sorbitan monopalmitate (SMP) is a food additive, permitted by the EU. It is entry E495 in the E number list of permitted food additives. It is also known under the trade name Span 40.

References

  1. Ingredients – Sorbitan Monostearate at sci-toys.com
  2. Current EU approved additives and their E Numbers, Food Standards Agency, 26 November 2010
  3. The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 18 March 2010.