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Conditions | Yield |
---|---|
With lithium perchlorate for 5h; Heating; | 98% |
With 1H-imidazole In acetonitrile at 20℃; for 10h; | 98% |
With Sulfuric acid immobilized on silica gel at 20℃; for 1h; neat (no solvent); | 91% |
Conditions | Yield |
---|---|
With copper(II) perchlorate hexahydrate In neat (no solvent) at 20℃; for 0.5h; Inert atmosphere; | 97% |
With iodine at 50℃; for 0.166667h; Microwave irradiation; | 96% |
With butylmethylimidazolium dicyanamide at 25℃; for 24h; | 93% |
(1,4,6-tri-O-benzoyl-β-D-fructofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside
acetic anhydride
sucrose octaacetate
Conditions | Yield |
---|---|
Stage #1: (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; Stage #2: With acetic acid In tetrahydrofuran; methanol Inert atmosphere; Stage #3: acetic anhydride With pyridine; dmap Inert atmosphere; | 96% |
Conditions | Yield |
---|---|
With iodine at 20℃; for 0.5h; | 92% |
1',2,3,3',4',6'-hexa-O-acetyl sucrose
acetic anhydride
A
1,3,4,6,-tetra-O-acetyl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside
B
sucrose octaacetate
Conditions | Yield |
---|---|
In pyridine 1.) -70 deg C, 2.) -15 deg C, 72 h; | A 68% B 26% |
acetic anhydride
1',2,3,4,6,6'-hexa-O-acetylsucrose
A
1,3,6,-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
B
1',2,3,4,4',6,6'-hepta-O-acetylsucrose
C
sucrose octaacetate
Conditions | Yield |
---|---|
In pyridine 1)-15 degC, 17 h, 2) r.t., 24 h; | A 43% B 7% C 26% |
In pyridine 1) -15 degC, 17 h, 2) r.t., 24 h; | A 43% B 7% C 26% |
3-ketosucrose
acetic anhydride
A
allo-sucrose octaacetate
D
sucrose octaacetate
Conditions | Yield |
---|---|
With pyridine; sodium tetrahydroborate 1.) water, 2.) RT, 15 h; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; | A n/a B n/a C 37% D n/a |
Conditions | Yield |
---|---|
With trifluoroacetic anhydride |
acetic anhydride
(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl) 3,4,6-tri-O-benzyl-1-(2,2,6,6-tetramethyl-1-piperidinyl)-β-D-fructofuranoside
sucrose octaacetate
Conditions | Yield |
---|---|
With pyridine; ammonia; sodium 1) THF, -78 deg C, 4 h, 2) 0 deg C, 6 h; Yield given. Multistep reaction; |
acetic anhydride
2,3,4,6,6'-penta-O-acetyl-1'-O-p-toluenesulfonylsucrose
A
2,3,3',4,6,6'-hexa-O-acetyl-1',4'-anhydrosucrose
B
3,3',4,4',6,6'-hexa-O-acetyl-1',2-anhydrosucrose
C
sucrose octaacetate
Conditions | Yield |
---|---|
With methanol; sodium methylate 1) reflux, 24 h, 2) pyridine, r.t.; Yield given. Multistep reaction. Yields of byproduct given; |
1.Introduction of Sucrose octaacetate
The Sucrose octaacetate, also known as Octaacetylsucrose, is an acetylated derivative of sucrose with the formula C28H38O19. It belongs to the product categories of Biochemistry; Disaccharides; O-Substituted Sugars; Sugars. Its EINECS registry number is 126-14-7. With the CAS registry number 126-14-7, its IUPAC name is Acetic acid [(2S,3S,4R,5R)-4-acetoxy-2,5-bis(acetoxymethyl)-2-[ [(2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6- (acetoxymethyl)-2-tetrahydropyranyl]oxy]-3-tetrahydrofuranyl] ester. It is a white to creamy white powder.
2. Physical properties of Sucrose octaacetate
(1)ACD/LogP: 3.19; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 3.19; (4)ACD/LogD (pH 7.4): 3.19; (5)ACD/BCF (pH 5.5): 156.72; (6)ACD/BCF (pH 7.4): 156.72; (7)ACD/KOC (pH 5.5): 1296.82; (8)ACD/KOC (pH 7.4): 1296.82; (9)#H bond acceptors: 19; (10)#Freely Rotating Bonds: 21; (11)Index of Refraction: 1.508; (12)Molar Refractivity: 147.52 cm3; (13)Molar Volume: 494.4 cm3; (14)Surface Tension: 53.5 dyne/cm; (15)Density: 1.37 g/cm3; (16)Flash Point: 275 °C; (17)Enthalpy of Vaporization: 98.22 kJ/mol; (18)Boiling Point: 668.3 °C at 760 mmHg; (19)Vapour Pressure: 1.01E-17 mmHg at 25°C.
3.Structure descriptors of Sucrose octaacetate
(1)SMILES: O=C(O[C@H]1[C@H](O[C@H](COC(=O)C)[C@@H](OC(=O)C)[C@@H]1OC(=O)C)O[C@@]2(O[C@@H]([C@@H](OC(=O)C)[C@@H]2OC(=O)C)COC(=O)C)COC(=O)C)C
(2)InChI: InChI=1/C28H38O19/c1-12(29)37-9-20-22(40-15(4)32)24(42-17(6)34)25(43-18(7)35)27(45-20)47-28(11-39-14(3)31)26(44-19(8)36)23(41-16(5)33)21(46-28)10-38-13(2)30/h20-27H,9-11H2,1-8H3/t20-,21-,22-,23-,24+,25-,26+,27-,28+/m1/s1
(3)InChIKey: ZIJKGAXBCRWEOL-SAXBRCJIBA
4.Uses of Sucrose octaacetate
It is used commercially and industrially in a variety of applications. It is used as an inert ingredient in pesticides and herbicides. Sucrose octaacetate has been approved by the FDA as a food additive. It has a bitter taste which has led to its use as bitterant and an aversive agent. The chemical has also been used to determine tasters from non-tasters in mice.
5. Safety information of Sucrose octaacetate
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable gloves and eye/face protection.
6. The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
rabbit | LD50 | skin | > 5gm/kg (5000mg/kg) | Food and Chemical Toxicology. Vol. 20, Pg. 827, 1982. | |
rat | LD50 | oral | > 5gm/kg (5000mg/kg) | Food and Chemical Toxicology. Vol. 20, Pg. 827, 1982. |