white to creamy white powder
Sucrose octaacetate is odorless with an intensly bitter flavor influenced by food acids
Sucrose octaacetate occurs as white hygroscopic powder. It is
practically odorless with a bitter taste.
Adhesive; impregnating and insulating papers; in lacquers and plastics; as a denaturant for alcohol.
Octa-O-acetyl D-(+)-Surcose was used in studies involving human bitter taste receptor hTAS2R46.
ChEBI: Sucrose octaacetate is a glycoside.
Sucrose octaacetate is typically produced by chemical synthesis; one
reported synthetic method is by pyridine-catalyzed acetylation of
sucrose.
May be prepared by heating sucrose, acetamide and sodium acetate; or by acetylation of sucrose using acetic anhydride, zinc chloride and acetic acid.
Pharmaceutical Applications
Sucrose octaacetate is used as an alcohol denaturant in pharmaceutical
formulations. It is also used as a bittering agent, and is
incorporated into preparations intended to deter nail-biting or
thumb-sucking.
Slightly toxic by ingestion andskin contact. A skin irritant. When heated todecomposition it emits acrid smoke and irritating vapors.
Sucrose octaacetate is generally regarded as safe. It is considered
slightly hazardous in cases of skin contact (irritant), ingestion, or
inhalation.
LD50 (rabbit, skin): >5 g/kg
LD50 (rat, oral): >5 g/kg
Sucrose octaacetate is a stable material and should be stored in a
well-closed, airtight container. Store in a cool, dry place; moisture
may cause instability.
After three recrystallisations from EtOH or 95% EtOH (charcoal), the m of the octaacetate rises to 88-90o, or Et2O with m 89o and [] D +58.5o (c 2.6, EtOH). It has a bitter taste. [Linstead et al. J Am Chem Soc 62 3260 1940, Lemieux & Huber J Am Chem Soc 78 4117 1956, Beilstein 17/8 V 410.]
GRAS listed. Approved by the FDA as both a direct and an indirect
food additive, and as a nail-biting deterrent for over-the-counter
drug products.
