Chemical Properties
Sucrose octaacetate is odorless with an intensly bitter flavor influenced by food acids
Chemical Properties
Sucrose octaacetate occurs as white hygroscopic powder. It is
practically odorless with a bitter taste.
Chemical Properties
white to creamy white powder
Uses
Adhesive; impregnating and insulating papers; in lacquers and plastics; as a denaturant for alcohol.
Uses
Octa-O-acetyl D-(+)-Surcose was used in studies involving human bitter taste receptor hTAS2R46.
Definition
ChEBI: Sucrose octaacetate is a glycoside.
Preparation
May be prepared by heating sucrose, acetamide and sodium acetate; or by acetylation of sucrose using acetic anhydride, zinc chloride and acetic acid.
Production Methods
Sucrose octaacetate is typically produced by chemical synthesis; one
reported synthetic method is by pyridine-catalyzed acetylation of
sucrose.
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.
Safety Profile
Slightly toxic by ingestion andskin contact. A skin irritant. When heated todecomposition it emits acrid smoke and irritating vapors.
Safety
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
storage
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.
Purification Methods
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.]
Regulatory Status
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.
