Sorbitan monooleate

from Wikipedia, the free encyclopedia
Structural formula
Structure of sorbitan monooleate
General
Surname Sorbitan monooleate
other names
  • E  494
  • SORBITAN OLEATE ( INCI )
  • Span 80 (brand name)
Molecular formula C 24 H 44 O 6
External identifiers / databases
CAS number 1338-43-8
EC number 215-665-4
ECHA InfoCard 100.014.242
PubChem 9920342
ChemSpider 8095979
Wikidata Q2303156
properties
Molar mass 428.60 g mol −1
density

0.99 g / mL at 20 ° C
1.01 g / mL

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sorbitan monooleate is a sorbitan fatty acid ester , an ester of sorbitol or 1,4-sorbitan anhydride ( sorbitan for short ) with a fatty acid , mainly oleic acid , linoleic acid and palmitic acid . It is used in the food industry and for pharmaceutical and cosmetic preparations as an emulsifier . It is approved in the EU under the number E 494 as a food additive for certain foods (including various baked goods, ice cream, desserts and sugar products and creamer ). The permitted daily dose is 5 mg / kg body weight and day. It is also used in forensics to extract explosives in order to identify them using gas chromatography coupled with mass spectrometry .

properties

Sorbitan monooleate used pharmaceutically is a mixture which is generally obtained by esterifying sorbitol and / or its mono- and dianhydrides with oleic acid in a molar ratio of 1: 1. The oleic acid content in the fatty acid fraction is 65.0 to 88.0%. It also contains linoleic acid (maximum 18.0%), palmitic acid (maximum 16.0%), palmitoleic acid (maximum 8.0%), stearic acid (maximum 6.0%), myristic acid (maximum 5.0%), linolenic acid ( maximum 4.0%) and fatty acids with a chain length of more than 18 carbon atoms (maximum 4.0%). Pharmaceutical sorbitan monooleate is a brownish yellow, viscous liquid with a relative density of about 0.99 and practically insoluble but dispersible in water. It is soluble in fatty oils to form a cloudy solution and is miscible with ethanol 96%. The acid number is at most 8.0 and the hydroxyl number 190 to 210. The HLB value is 4.3.

See also

Individual evidence

  1. ↑ Entry on E 494: Sorbitan monooleate in the European database for food additives, accessed on June 28, 2020.
  2. ↑ Entry on SORBITAN OLEATE in the CosIng database of the EU Commission, accessed on April 12, 2020.
  3. ↑ a b c d Datasheet Span ® 80 from Sigma-Aldrich , accessed on March 23, 2020 ( PDF ).
  4. ↑ a b Sorbitan Esters (Sorbitan Fatty Acid Esters) . In: Handbook of Pharmaceutical Excipients , 6th edition. RC Rowe, PJ Sheskey, ME Quinn. Pharmaceutical Press, London, 2009. p. 675 ff.
  5. ↑ Alicja Mortensen, Fernando Aguilar u. a .: Re ‐ evaluation of sorbitan monostearate (E491), sorbitan tristearate (E492), sorbitan monolaurate (E493), sorbitan monooleate (E494) and sorbitan monopalmitate (E495) when used as food additives. In: EFSA Journal. 15, 2017, doi: 10.2903 / j.efsa.2017.4788 .
  6. ↑ Fei-Fei Tian, ​​Jing Yu, Jia-Hong Hu, Yong Zhang, Meng-Xia Xie, Yuan Liu, Xiang-Feng Wang, Hai-Ling Liu, Jie Han: Determination of emulsion explosives with Span-80 as emulsifier by gas chromatography - mass spectrometry. In: Journal of Chromatography A. 1218, 2011, p. 3521, doi: 10.1016 / j.chroma.2011.03.065 .
  7. ↑ European Pharmacopoeia , 8th edition, basic work 2024, p. 4855 f.