Sucrose octaacetate

Sucrose octaacetate Property

Melting point:

82-85 °C(lit.)

Boiling point:

260 °C(lit.)

alpha 

D25.4 +58.5° (c = 2.56 in abs alcohol)

Density 

1.28

FEMA 

3038 | SUCROSE OCTAACETATE

refractive index 

60 ° (C=2, EtOH)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)

form 

Powder

color 

White to creamy white

Odor

odorless

Odor Type

odorless

optical activity

[α]22/D +58.8°, c = 2.5 in ethanol

Water Solubility 

SLIGHTLY SOLUBLE

Merck 

14,8881

BRN 

79290

InChIKey

ZIJKGAXBCRWEOL-SAXBRCJISA-N

LogP

3.19

CAS DataBase Reference

126-14-7(CAS DataBase Reference)

NIST Chemistry Reference

Sucrose, octaacetate(126-14-7)

EPA Substance Registry System

Sucrose octaacetate (126-14-7)

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

24/25-37/39-26

WGK Germany 

2

RTECS 

WN6620000

F 

3

HS Code 

29400090

Toxicity

LD50 orally in Rabbit: 5000 mg/kg LD50 dermal Rabbit 5000 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Sucrose octaacetate Chemical Properties,Usage,Production

Chemical Properties

white to creamy white powder

Chemical Properties

Sucrose octaacetate occurs as white hygroscopic powder. It is practically odorless with a bitter taste.

Chemical Properties

Sucrose octaacetate is odorless with an intensly bitter flavor influenced by food acids

Uses

LC-MS Analysis of Sucralose and Sucrose Octacetate on Ascentis RP-Amide

Uses

Octa-O-acetyl D-(+)-Surcose was used in studies involving human bitter taste receptor hTAS2R46.

Uses

Adhesive; impregnating and insulating papers; in lacquers and plastics; as a denaturant for alcohol.

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.