126-14-7 Usage
Chemical Properties
Different sources of media describe the Chemical Properties of 126-14-7 differently. You can refer to the following data:
1. white to creamy white powder
2. Sucrose octaacetate occurs as white hygroscopic powder. It is
practically odorless with a bitter taste.
3. Sucrose octaacetate is odorless with an intensly bitter flavor influenced by food acids
Uses
Different sources of media describe the Uses of 126-14-7 differently. You can refer to the following data:
1. LC-MS Analysis of Sucralose and Sucrose Octacetate on Ascentis RP-Amide
2. Octa-O-acetyl D-(+)-Surcose was used in studies involving human bitter taste receptor hTAS2R46.
3. Adhesive; impregnating and insulating papers; in lacquers and plastics; as a denaturant for alcohol.
Production Methods
Sucrose octaacetate is typically produced by chemical synthesis; one
reported synthetic method is by pyridine-catalyzed acetylation of
sucrose.
Preparation
May be prepared by heating sucrose, acetamide and sodium acetate; or by acetylation of sucrose using acetic anhydride, zinc chloride and acetic acid.
Pharmaceutical Applications
Sucrose octaacetate is used as an alcohol denaturant in pharmaceutical
formulations. It is also used as a bittering agent, and is
incorporated into preparations intended to deter nail-biting or
thumb-sucking.
Safety Profile
Slightly toxic by ingestion andskin contact. A skin irritant. When heated todecomposition it emits acrid smoke and irritating vapors.
Safety
Sucrose octaacetate is generally regarded as safe. It is considered
slightly hazardous in cases of skin contact (irritant), ingestion, or
inhalation.
LD50 (rabbit, skin): >5 g/kg
LD50 (rat, oral): >5 g/kg
storage
Sucrose octaacetate is a stable material and should be stored in a
well-closed, airtight container. Store in a cool, dry place; moisture
may cause instability.
Purification Methods
After three recrystallisations from EtOH or 95% EtOH (charcoal), the m of the octaacetate rises to 88-90o, or Et2O with m 89o and [] D +58.5o (c 2.6, EtOH). It has a bitter taste. [Linstead et al. J Am Chem Soc 62 3260 1940, Lemieux & Huber J Am Chem Soc 78 4117 1956, Beilstein 17/8 V 410.]
Regulatory Status
GRAS listed. Approved by the FDA as both a direct and an indirect
food additive, and as a nail-biting deterrent for over-the-counter
drug products.
Check Digit Verification of cas no
The CAS Registry Mumber 126-14-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,2 and 6 respectively; the second part has 2 digits, 1 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 126-14:
(5*1)+(4*2)+(3*6)+(2*1)+(1*4)=37
37 % 10 = 7
So 126-14-7 is a valid CAS Registry Number.
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
126-14-7Relevant articles and documents
A phenylpropanoid glycoside from Vaccaria segetalis
Sang, Shengmin,Lao, Aina,Wang, Hongcheng,Chen, Zhongliang,Uzawa, Jun,Fujimoto, Yasuo
, p. 569 - 571 (1998)
A new phenylpropanoid glycoside, named segetoside A, and a known compound, allantoin, have been isolated from the seeds of Vaccaria segetalis. On the basis of chemical and spectral data, the structure of segetoside A has been established as α-D-(6-O-dihydroferuloyl)glucopyranosyl(1 → 2)-β-D- fructofuranoside.
-
Cox et al.
, p. 968 (1933)
-
-
Ness,Fletcher
, p. 465,467 (1971)
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Tandem acetalation-acetylation of sugars and related derivatives with enolacetates under solvent-free conditions
Mukherjee, Debaraj,Shah, Bhahwal Ali,Gupta, Pankaj,Taneja, Subhash Chandra
, p. 8965 - 8968 (2007)
(Chemical Equation Presented) Molecular iodine catalyzes acetalation and acetylation of reducing sugars and sugar glycosides with stoichiometric amounts of enol acetates under solvent-free conditions, thereby facilitating the synthesis of various types of orthogonally protected sugar derivatives in short time and good yields. The outcome of the reaction can be controlled by variation in temperature. Thus at lower temperature, it is possible to obtain the acetonide acetate as a single product whereas peracetate is the major product at higher temperature.
I2/ionic liquid as a highly efficient catalyst for per-O-acetylation of sugar under microwave irradiation
Xiong, Xingquan,Yi, Chao,Han, Qian,Shi, Lin,Li, Sizhong
, p. 237 - 243 (2015/09/28)
A practical and highly efficient approach was developed to synthesize peracetylated sugar derivatives using a recyclable iodine/PEG400-based ionic liquid catalyst (I2/IL). The peracetylated sugars were readily obtained in a few minutes in excellent yields (90%-99%, 13 examples) on a multi-gram scale (50.0 mmol) by the reaction of sugar and acetic anhydride under microwave irradiation in the absence of a volatile organic solvent. The desired product was easily obtained by simple extraction with toluene from the reaction mixture, and I2/ILs can be readily recovered and reused at least six times without obvious loss in the yield. When the scale of the per-O-acetylation reaction was increased to 50.0 mmol, the desired product was still obtained in 90% yield after five recycles.
Synthesis of (+)-sucrose via β-d-psicofuranosylation
Uenishi, Jun'ichi,Ueda, Atsushi
experimental part, p. 2210 - 2217 (2009/04/04)
Despite the difficulty of direct β-furanosylation with d-fructose, the synthesis of β-d-fructofuranosyl α-d-glucopyranoside, (+)-sucrose 1, has been achieved stepwise, via β-selective d-psicofuranosylation followed by stereo inversion of a hydroxy group at the C-3 position on the furanose ring. d-Psicofuranosyl donor 10 was prepared in eight steps from d-ribose monoacetonide 3 in excellent yield.
