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Key Documents

252603

Sigma-Aldrich

D-(+)-Sucrose octaacetate

98%

Synonym(s):

Octa-O-acetylsucrose, SOA, Sucrose octaacetate

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About This Item

Empirical Formula (Hill Notation):
C28H38O19
CAS Number:
Molecular Weight:
678.59
Beilstein:
79290
EC Number:
MDL number:
UNSPSC Code:
12352108
PubChem Substance ID:
NACRES:
NA.22

Assay

98%

form

powder

optical activity

[α]22/D +58.8°, c = 2.5 in ethanol

bp

260 °C (lit.)

mp

82-85 °C (lit.)

SMILES string

CC(=O)OC[C@H]1O[C@H](O[C@]2(COC(C)=O)O[C@H](COC(C)=O)[C@@H](OC(C)=O)[C@@H]2OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O

InChI

1S/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

InChI key

ZIJKGAXBCRWEOL-SAXBRCJISA-N

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Application

Sucrose octaacetate (SOA) is a bitter-tasting acetylated sugar that is commonly used to study gustatory sensitivity in mice.
  • SOA can undergo partial deacetylation by lipases or proteases to form analogs, which are useful intermediates for synthesizing artificial sweeteners.
  • It can also be used as an in situ seed and a soft template to synthesize polyaniline (PANI) nanofibers under acidic conditions by the oxidative polymerization of aniline using ammonium peroxydisulfate (APS) as an oxidizing agent.

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sucrose octaacetate-taster mice have more vallate taste buds than non-tasters .
Miller Jr I J and Whitney G
Neuroscience Letters, 100(1-3) (1989)
Regioselective enzymatic deacetylation of sucrose octaacetate in organic solvents.
Palmer D C and Terradas F
Tetrahedron Letters, 35(11), 1673-1676 (1994)
Sucrose octaacetate tasting in a heterogeneous population of CFW mice.
Gannon K S and Whitney G
Behavior Genetics, 19(3), 417-431 (1989)
{Human taste thresholds for sucrose octaacetate.
Boughter Jr J D and Whitney G
Chemical Senses, 18(4), 445-448 (1993)
Synthesis of polyaniline nanostructures via soft template of sucrose octaacetate.
Qiu H, et al.
Synt. Metals, 160(11-12), 1179-1183 (2010)

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