Sucrose octaacetate

Base Information

• Chemical Name: Sucrose octaacetate
• CAS No.: 126-14-7
• Deprecated CAS: 68006-08-6,94273-23-1
• Molecular Formula: C28H38O19
• Molecular Weight: 678.598
• Hs Code.: 29400090
• European Community (EC) Number: 204-772-1
• UNII: 07V591057T
• DSSTox Substance ID: DTXSID3042423
• Nikkaji Number: J5.550F
• Wikipedia: Sucrose_octaacetate
• Wikidata: Q410482
• ChEMBL ID: CHEMBL2105790
• Mol file: 126-14-7.mol

Synonyms:octaacetyl sucrose;sucrose octa acetate;sucrose octaacetate;sucrose octaacetate, ((alpha-D)-fructofuranosyl)-isomer

Chemical Property of Sucrose octaacetate

Chemical Property:

• Appearance/Colour: white to creamy white powder
• Vapor Pressure: 1.01E-17mmHg at 25°C
• Melting Point: 82-85 °C(lit.)
• Refractive Index: 60 ° (C=2, EtOH)
• Boiling Point: 668.3 °C at 760 mmHg
• Flash Point: 275 °C
• PSA: 238.09000
• Density: 1.28 g/cm³
• LogP: -0.82920
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• Water Solubility.: SLIGHTLY SOLUBLE
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 21
• Exact Mass: 678.20072898
• Heavy Atom Count: 47
• Complexity: 1210

Purity/Quality:

99% ^*data from raw suppliers

Sucrose octaacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Disaccharides
• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OC2(C(C(C(O2)COC(=O)C)OC(=O)C)OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric 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
• Uses: LC-MS Analysis of Sucralose and Sucrose Octacetate on Ascentis RP-Amide Octa-O-acetyl D-(+)-Surcose was used in studies involving human bitter taste receptor hTAS2R46. Adhesive; impregnating and insulating papers; in lacquers and plastics; as a denaturant for alcohol.

Technology Process of Sucrose octaacetate

There total 14 articles about Sucrose octaacetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

sucrose (57-50-1) + acetic anhydride (108-24-7) → sucrose octaacetate (126-14-7)

Guidance literature:

With lithium perchlorate; for 5h; Heating;

DOI:10.1016/j.tet.2004.06.138

Reference yield: 97.0%

acetic anhydride (108-24-7) + Sucrose (57-50-1) → sucrose octaacetate (126-14-7)

Guidance literature:

With copper(II) perchlorate hexahydrate; In neat (no solvent); at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1039/c5ra03461b

Reference yield: 96.0%

(1,4,6-tri-O-benzoyl-β-D-fructofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside (1092961-95-9) + acetic anhydride (108-24-7) → sucrose octaacetate (126-14-7)

Guidance literature:

(1,4,6-tri-O-benzoyl-β-D-fructofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside; With ammonia; sodium; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

With acetic acid; In tetrahydrofuran; methanol; Inert atmosphere;

acetic anhydride; With pyridine; dmap; Inert atmosphere;

DOI:10.1016/j.tetasy.2008.09.008

upstream raw materials:

acetic anhydride

Sucrose

acetic acid

1',2,3,3',4',6'-hexa-O-acetyl sucrose

Downstream raw materials:

3,4,-di-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

1,3,4'-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

2,3,6,3',4'-pentaacetyl sucrose (6-PAS)

3,4,6-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Refernces

• 1、 Stanek,Cerna. "-". . p. 329. Retrieved 1963.
• 2、 R. Van Heerden, Fanie,Vincent Brandt,G. Roux, David. "Isolation and synthesis of trans- and cis-(-)-clovamides and their deoxy analogues from the bark of Dalbergia melanoxylon". . p. 2125 - 2129. Retrieved 1980.
• 3、 Forsyth, Stewart A.,MacFarlane, Douglas R.,Thomson, Robin J.,Von Itzstein, Mark. "Rapid, clean, and mild O-acetylation of alcohols and carbohydrates in an ionic liquid". . p. 714 - 715. Retrieved 2002.
• 4、 Chatterjee, Debnath,Paul, Abhijit,Rajkamal,Yadav, Somnath. "Cu(ClO4)2·6H2O catalyzed solvent free per-O-acetylation and sequential one-pot conversions of sugars to thioglycosides". . p. 29669 - 29674. Retrieved 2015/05/20.
• 5、 Zhang, Jianbo,Zhang, Bo,Zhou, Jiafen,Li, Juan,Shi, Chunjuan,Huang, Ting,Wang, Zhongfu,Tang, Jie. "H2SO4-SiO2: Highly efficient and reusable catalyst for per-O-acetylation of carbohydrates under solvent-free conditions". experimental part. p. 165 - 177. Retrieved 2012/01/19.