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Sucrose octaacetate

Alias: NSC-1695; NSC 1695; Sucrose octaacetate
Cat No.:V14474 Purity: ≥98%
Sucrose octaacetate is an acetylated analogue of sucrose that has a strong bitter taste and can be used as a bitter substitute.
Sucrose octaacetate
Sucrose octaacetate Chemical Structure CAS No.: 126-14-7
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Sucrose octaacetate is an acetylated analogue of sucrose that has a strong bitter taste and can be used as a bitter substitute. Sucrose octaacetate is used as a food additive and also as a binder and plasticizer. Sucrose octaacetate is also used in many pesticides, insecticides, and other toxic products to prevent accidental poisoning. Sucrose octaacetate can also be used as a soft template to synthesize polyaniline (PANI) nanofibers.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Because of its bitter taste, sucrose octaacetate is non-toxic and has a wide range of uses. For instance, sucrose octaacetate at a concentration of 0.06% (w/w) becomes excessively bitter when ingested. There are 255 distinct isomers and breakdown products that sucrose octaacetate can generate, and they all have extremely low molar absorptivities [1]. 2 and 3 g of sucrose octaacetate were used to create polyaniline (PANI) nanofibers and nanorods, respectively. An increase in sucrose octaacetate concentration led to the observation of nanostructures with irregularly formed agglomerates, such as particles and scaffolds. The molecular structure of the resultant polyaniline remains unaffected by the presence of sucrose octaacetate during the polymerization process, only causing morphological modifications. Due to its increased crystallinity, highly ordered structure, and electrical conductivity, 2 g of sucrose octaacetate-polymerized PANI exhibits higher thermal stability than 1, 3, and 4 g of PANI produced from sucrose octaacetate [3].
ln Vivo
No recombination between the sucrose octaacetate avoidance phenotype and the PRP haplotype was detected in any mouse population. Therefore, Soa and Prp are either very near or identical. To examine the latter hypothesis, two type A proline-rich protein genes (MP2 and M14) (∼30 kb apart at the Prp locus) were separately separated from a sucrose octaacetate taster inbred strain ( SWR) were transplanted to sucrose octaacetate-non-taste inbred line (FVB). In a two-bottle test, 5 MP2 transgenic mice and 7 M14 transgenic mice were insensitive to 1 mM sucrose octaacetate, thereby keeping the non-taste FVB phenotype. Expression of type A Prp gene mRNA alone or combined does not enhance SOA taste sensitivity in non-taster mice [2].
References

[1]. Chapter Five - Sucrose octaacetate. Profiles of Drug Substances, Excipients and Related Methodology. Volume 44, 2019, Pages 267-291.

[2]. Sucrose octaacetate avoidance in nontaster mice is not enhanced by two type-A Prp transgenes from taster mice. Chem Senses. 2000 Feb;25(1):39-45.

[3]. Synthesis of polyaniline nanostructures via soft template of sucrose octaacetate. Synthetic Metals.Volume 160, Issues 11–12, June 2010, Pages 1179-1183.

Additional Infomation
Sucrose octaacetate is a glycoside.
Sucrose octaacetate has been reported in Planchonella vitiensis with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C28H38O19
Molecular Weight
678.59
Exact Mass
678.2
CAS #
126-14-7
PubChem CID
31340
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
668.3±55.0 °C at 760 mmHg
Melting Point
82-85 °C(lit.)
Flash Point
275.0±31.5 °C
Vapour Pressure
0.0±2.0 mmHg at 25°C
Index of Refraction
1.509
LogP
3.19
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
19
Rotatable Bond Count
21
Heavy Atom Count
47
Complexity
1210
Defined Atom Stereocenter Count
9
SMILES
FC(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(C(C([H])([H])C([H])([H])C([H])([H])C([H])([H])OC1C(=C([H])C(C(=O)OC([H])([H])C([H])([H])C(C2C([H])=C(C3=C(C=2[H])C(C2C([H])=C(C([H])=C(C3=2)[N+](=O)[O-])[N+](=O)[O-])=O)[N+](=O)[O-])=O)=C([H])C=1OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)OC([H])([H])C([H])([H])C([H])([H])C([H])([H])C(C(C(C(C(C(C(C(F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)(F)F)F.O=C=C([H])[H]
InChi Key
ZIJKGAXBCRWEOL-SAXBRCJISA-N
InChi Code
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
Chemical Name
[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2S,3S,4R,5R)-3,4-diacetyloxy-2,5-bis(acetyloxymethyl)oxolan-2-yl]oxyoxan-2-yl]methyl acetate
Synonyms
NSC-1695; NSC 1695; Sucrose octaacetate
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~100 mg/mL (~147.36 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.07 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (3.07 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (3.07 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.4736 mL 7.3682 mL 14.7364 mL
5 mM 0.2947 mL 1.4736 mL 2.9473 mL
10 mM 0.1474 mL 0.7368 mL 1.4736 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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g/mol

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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