Sorbitan
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Names | |
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IUPAC name
(3S)-2-(1,2-Dihydroxyethyl)tetrahydrofuran-3,4-diol
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Other names
1,4-anhydrosorbitol
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Identifiers | |
12441-09-7 ![]() |
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Jmol 3D model | Interactive image |
PubChem | 103023 |
UNII | 6O92ICV9RU ![]() |
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Properties | |
C6H12O5 | |
Molar mass | 164.16 g/mol |
Appearance | colourless solid |
Vapor pressure | {{{value}}} |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references | |
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.[1] Sorbitan is primarily used in the production of surfactants such as polysorbates; which are important emulsifying agents.
Synthesis
Sorbitan is produced by the dehydration of sorbitol and is an intermediate in the conversion of sorbitol to isosorbide. The dehydration reaction usually produces sorbitan as a mixture of five- and six-membered cyclic ethers (1,4-anhydrosorbitol, 1,5-anhydrosorbitol and 1,4,3,6-dianhydrosorbitol)[2] with the five-membered 1,4-anhydrosorbitol form being the dominate product. The rate of formation of sorbitan is typically grater than that of isosorbide, which allows it to be produced selectively, providing the reaction conditions are carefully controlled. Interestingly, the dehydration reaction has been shown to work even in the presence of excess water.[3]
Surfactant derivatives
Esters
Sorbitan esters (also known as Spans) are nonionic surfactants that are used as emulsifying agents in the preparation of emulsions, creams, and ointments for pharmaceutical and cosmetic use. When used alone they produce stable water-in-oil emulsions but they are frequently used with a polysorbate in varying proportions to produce water-in-oil or oil-in-water emulsions or creams with a variety of different textures and consistencies. Sorbitan esters are also used as emulsifiers and stabilisers in food.[4]
- Sorbitan esters (Spans)
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Sorbitan monostearate (Span 60, E number: E491)
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Sorbitan tristearate.png
Sorbitan tristearate (Span 65, E number: E492)
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Sorbitan monolaurate.svg
Sorbitan monolaurate (Span 20, E number: E493)
Polysorbate
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Exothylated sorbitan esters are known as polysorbates (trade name: Tweens). They are an important class of emulsifiers used in a variety of settings, including pharmaceuticals and food.
References
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Merck Index, 12th Edition, 8872
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- Tetrahydrofurans
- Non-ionic surfactants