Sucrose octaacetate

Sucrose octaacetate

Names
IUPAC name Acetic acid [(2S,3S,4R,5R)-4-acetoxy-2,5-bis(acetoxymethyl)-2-[ [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6- (acetoxymethyl)-2-tetrahydropyranyl]oxy]-3-tetrahydrofuranyl] ester
Identifiers
CAS Number	126-14-7
Jmol interactive 3D	Image
PubChem	31340
SMILES CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)O[C@]2([C@H]([C@@H]([C@H](O2)COC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
Properties
Chemical formula	C28H38O19
Molar mass	678.59 g/mol
Appearance	needles
Density	1.27 g/cm^3 at 16 °C
Melting point	86.5 °C (187.7 °F; 359.6 K)
Boiling point	250 °C (482 °F; 523 K) at 1 mmHg
Solubility in water	slightly soluble in water
Solubility	soluble in ethanol, diethyl ether, acetone, benzene, chloroform[1]
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

Sucrose octaacetate is an acetylated derivative of sucrose. It is used commercially and industrially in a variety of applications. It is used as an inert ingredient in pesticides and herbicides. As of December 2005, sucrose octaacetate was determined by the EPA to be usable as an inert ingredient in pesticides due to its low toxicity.^[2]

Sucrose octaacetate has been approved by the FDA as a food additive. It has a bitter taste which has led to its use as bitterant and an aversive agent. The chemical has also been used to determine tasters from non-tasters in mice.^[3]

References

1. Lide, David R. (1998), Handbook of Chemistry and Physics (87 ed.), Boca Raton, FL: CRC Press, pp. 3–506, ISBN 0-8493-0594-2
2. Inert Reassessment: Sucrose Octaacetate (CAS Reg. No. 126-14-7)
3. Intermediate sucrose octa-acetate sensitivity suggests a third allele at mouse bitter taste locus Soa and Soa-Rua identity - Harder et al. 17 (4): 391 - Chemical Senses