Sucrose Octaacetate 707 17 Food Chemicals Codex, 6th edn. Bethesda, MD: United States Lipari JM, Reiland TL. Flavors and flavor modifiers. Swarbrick J, Boylan Pharmacopeia, 2008; 932. JC, eds. Encyclopedia of Pharmaceutical Technology, 2nd edn, vol. 2: New York: Marcel Dekker, 2002; 1255–1263. Wolraich ML et al. Effects of diets high in sucrose or aspartame on the 20 General References behavior and cognitive performance of children. N Engl J Med 1994; Armstrong NA. In: Swarbrick J, Boylan JC, eds. Encyclopedia of 330: 301–307. Pharmaceutical Technology, 2nd edn, vol. 3: New York: Marcel Dekker, 2002; 2713–2732. 21 Author European Directorate for the Quality of Medicines and Healthcare NA Armstrong. (EDQM). European Pharmacopoeia – State Of Work Of International Harmonisation. Pharmeuropa 2009; 21(1): 142–143. http://www.edq- m.eu/site/-614.html (accessed 3 February 2009). 22 Date of Revision Jackson EB, ed. Sugar Confectionery Manufacture. Glasgow: Blackie, 1990. 3 February 2009. Sucrose Octaacetate 1 Nonproprietary Names 8 Description USP-NF: Sucrose Octaacetate Sucrose octaacetate occurs as white hygroscopic powder. It is practically odorless with a bitter taste. 2 Synonyms a-D-Glucopyranoside, 1,3,4,6-tetra-O-acetyl-b-D-fructofuranosyl-, 9 Pharmacopeial Specifications tetraacetate; octaacetylsucrose. See Table I. 3 Chemical Name and CAS Registry Number Table I: Pharmacopeial specifications for sucrose octaacetate. Acetic acid[(2S,3S,4R,5R)-4-acetoxy-2,5-bis(acetoxymethyl)-2- Test USP32–NF27 [[(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)-2-tetra- hydropyranyl]oxy]-3-tetrahydrofuranyl]ester [126-14-7] Water 41.0% Residue on ignition 40.1% Melting temperature 4788C 4 Empirical Formula and Molecular Weight Acidity þ Assay (anhydrous) 98.0–100.5% C28H38O19 678.59 5 Structural Formula 10 Typical Properties S Boiling point 2608C Flash point 307.38C Melting point 898C (decomposes above 2858C) Refractive index 1.47 Solubility see Table II. Specific gravity 1.28 at 208C (water = 1) 25.4 Specific rotation [a]D = þ58.58 Table II: Solubility of sucrose octaacetate. Solvent Solubility at 208C Acetone 1 in 0.3 Benzene 1 in 0.6 Ethanol (95%) 1 in 11 6 Functional Category Glacial acetic acid 1 in 0.7 Toluene 1 in 0.5 Alcohol denaturant; bittering agent. Water 1 in 1100 7 Applications in Pharmaceutical Formulation or Technology Sucrose octaacetate is used as an alcohol denaturant in pharma- 11 Stability and Storage Conditions ceutical formulations. It is also used as a bittering agent, and is Sucrose octaacetate is a stable material and should be stored in a incorporated into preparations intended to deter nail-biting or well-closed, airtight container. Store in a cool, dry place; moisture thumb-sucking. may cause instability. 708 Sucrose Octaacetate SEM 1: Excipient: sucrose octaacetate; manufacturer: Sigma-Aldrich Inc.; LD50 (rabbit, skin): >5 g/kg lot no.: RS33841’08; magnification: 100Â; voltage: 5 kV. (3) LD50 (rat, oral): >5 g/kg 15 Handling Precautions Observe normal precautions appropriate to the circumstances and quantity of the material handled. When heated to decomposition, sucrose octaacetate emits acrid smoke and irritating vapors. Compatible chemical-resistant gloves and eye safety goggles are recommended. Respiratory protection is not required, but dust masks may be used for protection from nuisance levels of dust. 16 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.(4) 17 Related Substances Sodium acetate; sucrose. SEM 2: Excipient: sucrose octaacetate; manufacturer: Sigma-Aldrich Inc.; 18 Comments lot no.: RS33841’08; magnification: 500Â; voltage: 5 kV. Sucrose octaacetate is a naturally occurring substance that has been isolated from plant material: the root of Clematis japonica contains 0.15% of sucrose octaacetate by dry weight. At a concentration of 0.06% sucrose octaacetate renders sugar too bitter for human consumption.(5) The EINECS number for sucrose octaacetate is 204-772-1. The PubChem Compound ID (CID) for sucrose octaacetate is 219904. 19 Specific References 1 Amagasa M, Yanagita T. Industrial uses of cane sugar I. Catalytic effects of pyridine on the acetylation of sucrose. Kogyo Kagaku Zasshi 1940; 43(Suppl.): 444–445. 2 Amagasa M, Tobisima H. Industrial uses of cane sugar II. The influence of temperature and the amount of acetic anhydride upon the acetylation of sucrose with pyridine as catalyst. Kogyo Kagaku Zasshi 1941; 44(Suppl.): 40–41. 3 Lewis RJ, ed. Sax’s Dangerous Properties of Industrial Materials, 11th edn. New York: Wiley, 2004; 2755. S 4 Jarvis CM. Reassessment of the exemption from the requirement of a tolerance for sucrose octaacetate (CAS Reg. No. 126-14-7). US EPA Memorandum, December 21, 2005: 1–10. 5 Thierry DM et al. Preparation of sucrose octaacetate – a bitter-tasting compound. J Chem Educ 1992; 69(8): 668–669. 12 Incompatibilities — 20 General References 13 Method of Manufacture Sciencelab, Inc. Material safety data sheet: Sucrose octaacetate, 9 October 2005. Sucrose octaacetate is typically produced by chemical synthesis; one reported synthetic method is by pyridine-catalyzed acetylation of (1,2) sucrose. 21 Authors RA Ferraina, DD Ladipo. 14 Safety Sucrose octaacetate is generally regarded as safe. It is considered slightly hazardous in cases of skin contact (irritant), ingestion, or 22 Date of Revision inhalation. 3 March 2009..