Sorbitan monopalmitate

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Sorbitan monopalmitate
Sorbitan monopalmitate.svg
Names
IUPAC name
1,4-Anhydro-D-glucitol 6-hexadecanoate
Systematic IUPAC name
(2R)-2-[(2R,3R,4S)-3,4-Dihydroxyoxolan-2-yl]-2-hydroxyethyl hexadecanoate
Other names
  • Sorbitan palmitate
  • Span 40
  • E495
Identifiers
ECHA InfoCard 100.043.229 OOjs UI icon edit-ltr-progressive.svg
E number E495 (thickeners, ...)
PubChem CID
UNII
Properties
C22H42O6
Molar mass 402.572 g·mol−1
Melting point 46–47 °C (115–117 °F; 319–320 K) [1]
Hazards
Flash point 113 °C (235 °F; 386 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sorbitan monopalmitate (SMP) is a food additive, [2] permitted by the EU. It is entry E495 in the E number list of permitted food additives. [3] It is also known under the trade name Span 40. [4]

Synopsis

Sorbitan monopalmitate has been known since at least 1959. [5]

Around 2000, SMP was permitted by the EU in bakery products, icings, marmalades, simulations of milk and cream, beverage whiteners, liquid concentrates of fruit and herbs, sorbets, emulsified sauces, food supplements and chewing gum amongst others. [3]

SMP is a polysorbate that is derived from the mixture of partial esters of sorbitol treated with palmitic acid. SMP is a lipophilic surfactant. It may be found in combination with polysorbates. It is used to modify crystallisation of fats. [3] It is insoluble in water. [6] Up to 25 mg/kg bodyweight can be processed by humans. SMP is metabolized to sorbitol and palmitic acid, without any apparent side effects. The use of animal fats, like pork, in the production of SMP is possible. [4]

Related Research Articles

SMP may refer to:

<span class="mw-page-title-main">Sorbitol</span> 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.

<span class="mw-page-title-main">Triglyceride</span> Any ester of glycerol having all three hydroxyl groups esterified with fatty acids

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.

<span class="mw-page-title-main">Tallow</span> Rendered form of beef or mutton fat

Tallow is a rendered form of beef or mutton suet, primarily made up of triglycerides.

<span class="mw-page-title-main">Stearic acid</span> Eighteen-carbon straight-chain fatty acid

Stearic acid is a saturated fatty acid with an 18-carbon chain. The IUPAC name is octadecanoic acid. It is a soft waxy solid with the formula CH3(CH2)16CO2H. The triglyceride derived from three molecules of stearic acid is called stearin. Stearic acid is a prevalent fatty-acid in nature, found in many animal and vegetable fats, but is usually higher in animal fat than vegetable fat. It has a melting point of 69.4 °C and a pKa of 4.50.

<span class="mw-page-title-main">Lecithin</span> 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.

<span class="mw-page-title-main">Palmitic acid</span> Chemical compound

Palmitic acid is a fatty acid with a 16-carbon chain. It is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D ratio is 16:0. It is a major component of palm oil from the fruit of Elaeis guineensis, making up to 44% of total fats. Meats, cheeses, butter, and other dairy products also contain palmitic acid, amounting to 50–60% of total fats.

<span class="mw-page-title-main">Polysorbate</span> Class of chemical compounds

Polysorbates are a class of emulsifiers used in some pharmaceuticals and food preparation. They are commonly used in oral and topical pharmaceutical dosage forms. They are also 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, Tween, and Kotilen.

Emulsifying wax is a cosmetic emulsifying ingredient. The ingredient name is often followed by the initials NF, indicating that it conforms to the specifications of the National Formulary.

<span class="mw-page-title-main">Polysorbate 80</span> Nonionic surfactant and emulsifier used in food and cosmetics

Polysorbate 80 is a nonionic surfactant and emulsifier often used in pharmaceuticals, foods, and cosmetics. This synthetic compound is a viscous, water-soluble yellow liquid.

<span class="mw-page-title-main">Ascorbyl palmitate</span> Chemical compound

Ascorbyl palmitate is an ester formed from ascorbic acid and palmitic acid creating a fat-soluble form of vitamin C. In addition to its use as a source of vitamin C, it is also used as an antioxidant food additive. It is approved for use as a food additive in the EU, the U.S., Canada, Australia, and New Zealand.

Polysorbate 20 is a polysorbate-type nonionic surfactant formed by the ethoxylation of sorbitan monolaurate. 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.

Sorbitan monostearate is an ester of sorbitan and stearic acid and is sometimes referred to as a synthetic wax.

In microbiology, the phenotypic testing of mycobacteria uses a number of methods. The most-commonly used phenotypic tests to identify and distinguish Mycobacterium strains and species from each other are described below.

<span class="mw-page-title-main">Sorbitan</span> 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 10,000 tons in 2012.

<span class="mw-page-title-main">Sorbitan tristearate</span> 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.

<span class="mw-page-title-main">Dough conditioner</span>

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.

Lactylates are organic compounds that are FDA approved for use as food additives and cosmetic ingredients, e.g. as food-grade emulsifiers. 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.

References

  1. 1 2 "Sorbitan monopalmitate". Sigma-Aldrich.
  2. "Compound Summary for CID 14927 - Sorbitan Monopalmitate". PubChem.
  3. 1 2 3 "E495 - Sorbitan monopalmitate, polyoxyethylene (20) sorbitan monopalmitate, polyoxethylene, Tween 40, sorbitan, monohexadecanoate.Polysorbate 40". The UK Food Guide.
  4. 1 2 "E 495: Sorbitane mono palmitate". FOOD-INFO.
  5. BELL Jr., JT (1959). "Polyoxyethylene sorbitan monopalmitate (tween 40) as a vehicle for oil red O fat stain". Stain Technology. 34 (4): 219–21. doi:10.3109/10520295909114678. PMID   13668771.
  6. "E495 (Sorbitan Monopalmitate) (SMP)". ERVESA.