Sorbitan fatty acid ester

Structure of sorbitol and its anhydride 1,4-sorbitan
Five-ring and six-ring forms of the sorbitan fatty acid ester

The sorbitan fatty acid esters (trade name for example Span ) are esters of sorbitol or its anhydrides ( sorbitan , isosorbide ) with one to three fatty acids each . Sorbitan can be formed from sorbitol by removing water .

The sorbitan component can be present in the compound both as a cyclic furanose (five-membered ring) and as a cyclic pyranose (six-membered ring) form. Since there are several OH groups in the sorbitol or sorbitan molecule , different isomers can arise in the representation .

Properties and use

Sorbitan fatty acid esters are cream-colored to amber-colored liquids or solids with a characteristic smell and taste. They are generally soluble in oils and also in most organic solvents. They are insoluble in water, but are usually dispersible. Sorbitan fatty acid esters serve to stabilize water-in-oil emulsions . Some esters are approved in the EU as food additives E 491, E 492, E 493, E 494 and E 495 only for use in certain foods with a fixed maximum amount.

These include:

Cakes and biscuits and puff pastries (with a maximum of 10 g / kg)
Chocolate and other cocoa products (maximum 10 g / kg)
Fruit jellies and jams (with a maximum of 25 mg / kg)
Ice cream (maximum 500 mg / kg)
Desserts and sugar confectionery (with a maximum of 5 g / kg)
Coffee creamer (maximum 5 g / kg)
Baker's yeast ( quantum satis )

Representative


Surname	E number	CAS number	Empirical molecular formula	HLB value	LD ₅₀	IUPAC name
Sorbitan monolaurate	E493	1338-39-2	C ₁₈ H ₃₄ O ₆	8.6	33.6 g kg ^-1 (oral, rat)	[2 - [(2 R , 3 S , 4 R ) -3,4-dihydroxytetrahydrofuran-2-yl] -2-hydroxy-ethyl] dodecanoate
Sorbitan monopalmitate	E 495	1338-40-5	C ₂₂ H ₄₂ O ₆	6.7		[2 - [(2 R , 3 S , 4 R ) -3,4-dihydroxytetrahydrofuran-2-yl] -2-hydroxy-ethyl] hexadecanoate
Sorbitan monostearate	E 491	1338-41-6	C ₂₄ H ₄₆ O ₆	4.7	31 g kg ^-1 (oral, rat)	[2 - [(2 R , 3 S , 4 R ) -3,4-dihydroxytetrahydrofuran-2-yl] -2-hydroxy-ethyl] octadecanoate
Sorbitan monoisostearate	-	71902-01-7	C ₂₄ H ₄₆ O ₆	4.7
Sorbitan monooleate	E 494	1338-43-8	C ₂₄ H ₄₄ O ₆	4.3		[2- (3,4-Dihydroxyoxolan-2-yl) -2-hydroxyethyl] - ( E ) -octadec-9-enoate
Sorbitan sesquioleate	-	8007-43-0	C ₃₃ H ₆₀ O _6.5	3.7		2- (3,4-Dihydroxyoxolan-2-yl) ethane-1,2-diol-mono / bis - [(9 Z ) -octadec-9-enoate]
Sorbitan tristearate	E 492	26658-19-5	C ₆₀ H ₁₁₄ O ₈	2.1		[2 - [(2 R , 3 S , 4 R ) -4-hydroxy-3-octadecanoyloxy-oxolan-2-yl] -2-octadecanoyloxy-ethyl] octadecanoate
Sorbitan trioleate	-	26266-58-0	C ₆₀ H ₁₀₈ O ₈	1.8		[(2R) -2 - [(3R, 4S) -4-hydroxy-3 - [(Z) -octadec-9-enoyl] oxyoxolan-2-yl] -2 - [(Z) -octadec-9-enoyl ] oxyethyl] - (Z) -octadec-9-enoate

Health assessments

The sorbitan fatty acid esters are considered to be toxicologically harmless. The permitted daily dose for the group of sorbitan fatty acid esters is 10 mg / kg body weight per day. This corresponds to the equivalent of 26 mg / kg body weight per day of sorbitan monostearate .

Derivatives

Ethoxylated sorbitan fatty acid esters ( polysorbates ) are also used as surfactants and emulsifiers.

Individual evidence

^ W. Baltes: Food chemistry . 6th edition. Springer, 2007, ISBN 978-3-540-38183-9 , pp. 175 , doi : 10.1007 / 978-3-540-38183-9 .
↑ ^a ^b ^c ^d ^e ^f ^g 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.
^ Hans-Dieter Belitz , Werner Grosch, Peter Schieberle : Textbook of food chemistry . 6th completely revised edition. Berlin 2007, ISBN 978-3-540-73201-3 , pp. 475 , doi : 10.1007 / 978-3-540-73202-0 .
↑ Regulation (EC) No. 1333/2008 in the consolidated version of October 28, 2019
^ Journal of the American College of Toxicology . Vol. 4 (3), p. 65, 1985.
↑ ^a ^b W. Baltes: Food chemistry . 6th edition. Springer, 2007, ISBN 978-3-540-38183-9 , pp. 177 , doi : 10.1007 / 978-3-540-38183-9 .
^ Food Research. Vol. 21, p. 348, 1956.
↑ 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 .

[1] W. Baltes: Food chemistry . 6th edition. Springer, 2007, ISBN 978-3-540-38183-9 , pp. 175 , doi : 10.1007 / 978-3-540-38183-9 .

[HoPE6-2] ↑ ^a ^b ^c ^d ^e ^f ^g 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.

[3] Hans-Dieter Belitz , Werner Grosch, Peter Schieberle : Textbook of food chemistry . 6th completely revised edition. Berlin 2007, ISBN 978-3-540-73201-3 , pp. 475 , doi : 10.1007 / 978-3-540-73202-0 .

[4] Regulation (EC) No. 1333/2008 in the consolidated version of October 28, 2019

[5] Journal of the American College of Toxicology . Vol. 4 (3), p. 65, 1985.

[baltes-hlb-6] W. Baltes: Food chemistry . 6th edition. Springer, 2007, ISBN 978-3-540-38183-9 , pp. 177 , doi : 10.1007 / 978-3-540-38183-9 .

[7] Food Research. Vol. 21, p. 348, 1956.

[efsa-8] 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 .