Sorbitan trioleate

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Structural formula
Structure of sorbitan trioleate
General
Surname Sorbitan trioleate
other names
  • ( Z , Z , Z ) sorbitan tri-9-octadecenoate
  • [(2 R ) -2 - [(3 R , 4 S ) -4-hydroxy-3 - [( Z ) -octadec-9-enoyl] oxyoxolan-2-yl] -2 - [( Z ) -octadec- 9-enoyl] oxyethyl] ( Z ) -octadec-9-enoate ( IUPAC )
  • SORBITAN TRIOLEATE ( INCI )
Molecular formula C 60 H 108 O 8
Brief description

Amber colored, viscous liquid

External identifiers / databases
CAS number 26266-58-0
EC number 247-569-3
ECHA InfoCard 100.043.230
PubChem 9920343
Wikidata Q27287216
properties
Molar mass 957.52 g mol −1
Physical state

liquid

solubility

practically insoluble but dispersible in water, soluble in fatty oils, somewhat soluble in ethanol

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
Toxicological data

> 39,800 mg kg −1 ( LD 50 , rat (male + female) ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sorbitan triolate (trade name for example Span 85 , Arlacel 85 ) is a sorbitan fatty acid ester , a triester of sorbitol or its anhydride sorbitan .

Extraction and presentation

Sorbitan trioleate is obtained by esterifying sorbitol or its monoanhydride with oleic acid in a molar ratio of 1: 3. Since the commercially available raw material “oleic acid” is a mixture of different fatty acids with oleic acid as the main component, the sorbitan trioleate obtained in this way is also a mixture of the esterification products with these fatty acids. The oleic acid used can be of animal or vegetable origin.

use

Sorbitan trioleate is used as a dispersant or emulsifier in human and veterinary medicinal products and in cosmetics as well as in other technical applications; it is considered biodegradable. It is not permitted as a food additive in the European Union, but is included in the Codex Alimentarius list of food additives with INS number 496.

Due to the very low HLB value of 1.8, water-in-oil emulsions (W / O emulsions) are formed, but it is mostly used in mixtures with other emulsifiers with a higher HLB value.

properties

Sorbitan trioleate used pharmaceutically contains 65.0 to 88.0% oleic acid in the fatty acid fraction. 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 trioleate is a pale yellow to pale yellow or brown, solid substance that turns into an amber-colored, oily or viscous liquid at around 25 ° C. The relative density is about 0.98.

See also

Individual evidence

  1. ↑ Entry on SORBITAN TRIOLEATE in the CosIng database of the EU Commission, accessed on April 12, 2020.
  2. ^ A b Rowe, Raymond C., Paul J. Sheskey, Quinn, Marian E.: Handbook of Pharmaceutical Excipients . Ed .: Pharmaceutical Press / American Pharmacists Association. 6th edition. RPS Publishing, London 2009, ISBN 978-0-85369-792-3 , pp. 675-678 .
  3. ↑ a b EDQM (Ed.): European Pharmacopoeia 9.0 . (Monograph No. 1044).
  4. ↑ a b c Datasheet Span ® 85, from Sigma-Aldrich , accessed on December 27, 2019 ( PDF ).
  5. ^ Croda homepage. Retrieved on February 9, 2017 (English, product search for SPAN 85).
  6. ↑ CAC / GL 36-1989 - Class Names and the International Numbering System for Food Additives. Retrieved January 26, 2017 (English).