Sucrose octaacetate supplier

Name
Sucrose octaacetate
EINECS 204-772-1
CAS No. 126-14-7
Article Data31
CAS DataBase
Density 1.28 g/cm³
Solubility slightly soluble in water
Melting Point 82-85 °C(lit.)
Formula C₂₈H₃₈O₁₉
Boiling Point 668.3 °C at 760 mmHg
Molecular Weight 678.598
Flash Point 275 °C
Transport Information
Appearance white to creamy white powder
Safety 24/25-37/39-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Sucrose,octaacetate (6CI,7CI,8CI);a-D-Glucopyranoside, 1,3,4,6-tetra-O-acetyl-b-D-fructofuranosyl, tetraacetate (9CI);2,3,4,6,1',3',4',6'-Octa-O-acetylsucrose;NSC 1695;Octa-O-acetylsucrose;Octaacetyl sucrose;Saccharose octaacetate;
PSA 238.09000
LogP -0.82920

Synthetic route

: 57-50-1
sucrose

: 108-24-7
acetic anhydride

: 126-14-7
sucrose octaacetate

Conditions

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%

: 108-24-7
acetic anhydride

: 57-50-1
Sucrose

: 126-14-7
sucrose octaacetate

Conditions

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%

: 1092961-95-9
(1,4,6-tri-O-benzoyl-β-D-fructofuranosyl) 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside

: 108-24-7
acetic anhydride

: 126-14-7
sucrose octaacetate

Conditions

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%

: 108-22-5
Isopropenyl acetate

: 57-50-1
Sucrose

: 126-14-7
sucrose octaacetate

Conditions

Conditions	Yield
With iodine at 20℃; for 0.5h;	92%

: 52706-47-5
1',2,3,3',4',6'-hexa-O-acetyl sucrose

: 108-24-7
acetic anhydride

A: 53269-82-2
1,3,4,6,-tetra-O-acetyl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside

B: 126-14-7
sucrose octaacetate

Conditions

Conditions	Yield
In pyridine 1.) -70 deg C, 2.) -15 deg C, 72 h;	A 68% B 26%

...Expand

: 108-24-7
acetic anhydride

: 102069-21-6
1',2,3,4,6,6'-hexa-O-acetylsucrose

A: 53269-83-3
1,3,6,-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

B: 105444-14-2
1',2,3,4,4',6,6'-hepta-O-acetylsucrose

C: 126-14-7
sucrose octaacetate

Conditions

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%

...Expand

: 1883-12-1
3-ketosucrose

: 108-24-7
acetic anhydride

A: 75800-69-0
allo-sucrose octaacetate

B: 2,3,6-tri-O-acetyl-α-D-allopyranosyl 1,3,4,6-tetra-O-acetyl-β-D-fructofuranoside

C: 2,4,6-tri-O-acetyl-α-D-allopyranosyl 1,3,4,6-tetra-O-acetyl-β-D-fructofuranoside

D: 126-14-7
sucrose octaacetate

Conditions

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

...Expand

: 64-19-7
acetic acid

: 57-50-1
Sucrose

: 126-14-7
sucrose octaacetate

Conditions

Conditions	Yield
With trifluoroacetic anhydride

: 108-24-7
acetic anhydride

: 129264-68-2
(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

: 126-14-7
sucrose octaacetate

Conditions

Conditions	Yield
With pyridine; ammonia; sodium 1) THF, -78 deg C, 4 h, 2) 0 deg C, 6 h; Yield given. Multistep reaction;

: 108-24-7
acetic anhydride

: 115520-96-2
2,3,4,6,6'-penta-O-acetyl-1'-O-p-toluenesulfonylsucrose

A: 88238-29-3
2,3,3',4,6,6'-hexa-O-acetyl-1',4'-anhydrosucrose

B: 73411-10-6, 115728-54-6
3,3',4,4',6,6'-hexa-O-acetyl-1',2-anhydrosucrose

C: 126-14-7
sucrose octaacetate

Conditions

Conditions	Yield
With methanol; sodium methylate 1) reflux, 24 h, 2) pyridine, r.t.; Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 108-24-7
acetic anhydride

: 57-50-1
Sucrose

A: 67831-76-9
1,3,4-Tri-O-acetyl-2,6-anhydro-β-D-fructofuranose

B: 118759-70-9
((2R,3S,4S,5R)-3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methyl acetate

C: 126-14-7
sucrose octaacetate

Conditions

Conditions	Yield
With triethylboraxine 1.) pyridine, toluene, 130 deg C (bath temp.), 22 h, 2.) 30 deg C, 8 h; Yield given. Multistep reaction. Yields of byproduct given;
Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: 108-24-7
acetic anhydride

: 57-50-1
Sucrose

A: 40984-21-2
2,3,4,1’,3’,4’-hexa-O-acetyl-6,6’-dideoxydiazidosucrose

B: 35014-72-3
6-Deoxy-6-azidol-hepta-O-acetylsaccharose

C: 126-14-7
sucrose octaacetate

Conditions

Conditions	Yield
Yield given. Multistep reaction. Yields of byproduct given;

...Expand

: Acetic acid (2R,3R,4S,5S)-4-acetoxy-2,5-bis-acetoxymethyl-2-((2R,4aR,6R,7R,8S,8aR)-7,8-diacetoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-tetrahydro-furan-3-yl ester

: 108-24-7
acetic anhydride

: 126-14-7
sucrose octaacetate

Conditions

Conditions	Yield
With perchloric acid at 20℃; for 0.333333h;

: 74-83-9
methyl bromide

: 126-14-7
sucrose octaacetate

: 5346-73-6
(2R,3R,4S,5R,6R)-2-((2S,3R,4S,5R)-3,4-Dimethoxy-2,5-bis-methoxymethyl-tetrahydro-furan-2-yloxy)-3,4,5-trimethoxy-6-methoxymethyl-tetrahydro-pyran

Conditions

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In benzene for 5h; Ambient temperature;	96%

: 126-14-7
sucrose octaacetate

: 57-50-1
Sucrose

Conditions

Conditions	Yield
magnesium oxide In methanol for 1h; Ambient temperature;	90%
With sodium methylate In methanol at 20℃; for 3h; Inert atmosphere;	90%
With methanol; potassium cyanide for 0.5h; Ambient temperature;	75%

: 126-14-7
sucrose octaacetate

: 53269-83-3
1,3,6,-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
With 25 mmol/l sodium phosphate buffer; Candida rugosa lipase immobilised on octyl agarose In acetonitrile at 25℃; pH=7.0; Kinetics; Product distribution; Further Variations:; Reagents;	77%
lipase type II from porcine pancreas In di-isopropyl ether at 45℃; for 24h; regioselective deacetylation with various enzymes;
lipase type II from porcine pancreas In di-isopropyl ether at 45℃; for 24h;

: 126-14-7
sucrose octaacetate

: 64644-60-6
3,4,6-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
With phosphate buffer; protease N In water; N,N-dimethyl-formamide at 37℃; for 96h; regioselective hydrolysis by various enzymes;	74%
With phosphate buffer; protease N In water; N,N-dimethyl-formamide at 37℃; for 96h;	74%
With magnesium chloride In aq. phosphate buffer; N,N-dimethyl-formamide at 35℃; for 48h; Reagent/catalyst; Solvent; Enzymatic reaction; regioselective reaction;	41%
With Alcalase In aq. phosphate buffer; water; N,N-dimethyl-formamide at 37℃; for 24h; pH=7; Enzymatic reaction;	27.4%

: 126-14-7
sucrose octaacetate

: 35520-98-0
3,4,-di-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
With phosphate buffer; Alcalase In water; N,N-dimethyl-formamide at 37℃; for 72h;	60%

: 126-14-7
sucrose octaacetate

A: 53269-83-3
1,3,6,-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

B: 64644-60-6
3,4,6-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
With phosphate buffer; Candida lipase In water; N,N-dimethyl-formamide at 37℃; for 96h;	A 54% B 6%

: 126-14-7
sucrose octaacetate

: 53269-82-2
1,3,4,6,-tetra-O-acetyl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
With phosphate buffer; Lipase AP6 In ethanol; water at 37℃; for 20h;	40%
Multi-step reaction with 2 steps 1: lipase Ap 12 from Aspergillus niger / diisopropyl ether / 24 h / 45 °C 2: silica gel View Scheme

: 126-14-7
sucrose octaacetate

: 30694-61-2
1,3,4,6,-tetra-O-acetyl-β-D-fructofuranosyl 2,3,4-tri-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
With phosphate buffer; sodium chloride; calcium chloride; Lipase AP6 at 37℃; for 20h;	40%

: 126-14-7
sucrose octaacetate

: 30694-62-3
1,3,4'-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
With phosphate buffer; sodium chloride; calcium chloride; chymotrypsin at 37℃; for 72h;	30%
SP-435 lipase from Candida antarctica In di-isopropyl ether at 45℃; for 24h;

: 126-14-7
sucrose octaacetate

A: 52706-47-5
1',2,3,3',4',6'-hexa-O-acetyl sucrose

B: 1,3,4,6-tetra-O-acetyl-β-D-fructofuranosyl 2-O-acetyl-α-D-glucopyranoside

C: 1,3,4,6-tetra-O-acetyl-β-D-fructofuranosyl 2,6-di-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
for 72h; Ambient temperature; lipase OF, phosphate buffer pH 7.0 (contg. NaCl and CaCl2);	A 25% B 26% C 7%
for 72h; Ambient temperature; lipase OF, phosphate buffer pH 7.0 (contg. NaCl and CaCl2);	A 25% B 26% C 7%

...Expand

: 126-14-7
sucrose octaacetate

A: 53269-83-3
1,3,6,-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

B: 53269-82-2
1,3,4,6,-tetra-O-acetyl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside

C: 30694-61-2
1,3,4,6,-tetra-O-acetyl-β-D-fructofuranosyl 2,3,4-tri-O-acetyl-α-D-glucopyranoside

D: 64644-60-6
3,4,6-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
With aluminum oxide Ambient temperature;	A 4% B 9% C 24% D 11%

...Expand

: 29848-79-1
methyl hexadecanoate-d31

: 126-14-7
sucrose octaacetate

sucrose octapalmitate-d248: sucrose octapalmitate-d248

Conditions

Conditions	Yield
With sodium at 80 - 110℃; for 2h; Esterification;	24%

: 126-14-7
sucrose octaacetate

: 102069-21-6
1',2,3,4,6,6'-hexa-O-acetylsucrose

Conditions

Conditions	Yield
With propylamine for 0.833333h; Mechanism; Ambient temperature; other sucrose derivative, other reagents, other time;	22%
With propylamine for 0.833333h; Ambient temperature;	22%

: 126-14-7
sucrose octaacetate

A: 53269-83-3
1,3,6,-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

B: 30694-62-3
1,3,4'-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

C: 102069-21-6
1',2,3,4,6,6'-hexa-O-acetylsucrose

D: 64644-60-6
3,4,6-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
With potassium carbonate on alumina In methanol for 6h; Ambient temperature; Further byproducts given. Yields of byproduct given;	A 15.65% B n/a C 14.24 % Chromat. D 7.62 % Chromat.
With potassium carbonate on alumina In methanol for 6h; Ambient temperature; Yield given. Further byproducts given;	A 15.65 % Chromat. B n/a C 14.24 % Chromat. D 7.62 % Chromat.
With potassium carbonate on alumina In methanol for 21h; Ambient temperature; Further byproducts given. Yields of byproduct given;	A 9.59 % Chromat. B n/a C 33.77 % Chromat. D 5.19 % Chromat.
With potassium carbonate on alumina In methanol for 6h; Ambient temperature; Further byproducts given;	A 15.65 % Chromat. B n/a C 14.24 % Chromat. D 7.62 % Chromat.

...Expand

: 16649-49-3
Acetic anhydride-d6

: 126-14-7
sucrose octaacetate

: perdeuteroacetylated of 2,3,4,6,3',4',6'-heptaacetyl sucrose

Conditions

Conditions	Yield
With perdeuteriopyridine at 45℃;

: 126-14-7
sucrose octaacetate

A: 35520-98-0
3,4,-di-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

B: 30694-62-3
1,3,4'-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

C: 35867-25-5
2,3,6,3',4'-pentaacetyl sucrose (6-PAS)

D: 64644-60-6
3,4,6-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
serine protease from Bacillus subtilis In di-isopropyl ether at 45℃; for 120h; Yield given. Yields of byproduct given;

...Expand

: 126-14-7
sucrose octaacetate

A: 35520-98-0
3,4,-di-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

B: 64644-60-6
3,4,6-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
serine protease from Bacillus subtilis In di-isopropyl ether at 45℃; for 24h; Yield given. Yields of byproduct given;

: 126-14-7
sucrose octaacetate

A: 53269-83-3
1,3,6,-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

B: 30694-62-3
1,3,4'-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

C: 102069-21-6
1',2,3,4,6,6'-hexa-O-acetylsucrose

D: 105444-14-2
1',2,3,4,4',6,6'-hepta-O-acetylsucrose

Conditions

Conditions	Yield
With potassium carbonate on alumina In methanol for 6h; Ambient temperature; Yield given. Further byproducts given. Title compound not separated from byproducts;	A 15.65 % Chromat. B n/a C 14.24 % Chromat. D n/a

...Expand

: 126-14-7
sucrose octaacetate

A: 53269-82-2
1,3,4,6,-tetra-O-acetyl-β-D-fructofuranosyl 2,3,6-tri-O-acetyl-α-D-glucopyranoside

B: 30694-61-2
1,3,4,6,-tetra-O-acetyl-β-D-fructofuranosyl 2,3,4-tri-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
lipase AP 12 from Aspergillus niger In di-isopropyl ether at 45℃; for 24h; Yield given. Yields of byproduct given;

: 126-14-7
sucrose octaacetate

A: 30694-62-3
1,3,4'-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

B: 64644-60-6
3,4,6-tri-O-acetyl-β-D-fructofuranosyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Conditions

Conditions	Yield
serine protease from Bacillus subtilis In di-isopropyl ether at 45℃; for 24h; Yield given. Yields of byproduct given;

Sucrose octaacetate Consensus Reports

Reported in EPA TSCA Inventory.

Sucrose octaacetate Specification

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.

Product Name

Sucrose octaacetate

Synthetic route

Sucrose octaacetate Consensus Reports

Sucrose octaacetate Specification

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