alpha-D-Glucopyranoside, alpha-D-glucopyranosyl

Base Information

• Chemical Name: alpha-D-Glucopyranoside, alpha-D-glucopyranosyl
• CAS No.: 99-20-7
• Molecular Formula: C12H22O11
• Molecular Weight: 342.3
• Hs Code.: 29400090
• NSC Number: 2093
• DSSTox Substance ID: DTXSID40859175
• Wikidata: Q104167739
• Mol file: 99-20-7.mol

Synonyms:B,B-TREHALOSE;1174299-27-4;2-(hydroxymethyl)-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxane-3,4,5-triol;NSC2093;.alpha.-D-Glucopyranoside, .alpha.-D-glucopyranosyl;2-(hydroxymethyl)-6-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-3,4,5-triol;.alpha.-Trehalose;.alpha.-D-Trehalose;Hexopyranosyl hexopyranoside;Trehalose, alpha,alpha'-;.alpha.,.alpha.-Trehalose;MFCD00006628;SCHEMBL137621;DTXSID40859175;HDTRYLNUVZCQOY-UHFFFAOYSA-N;BCP07695;SB19117;|A-D-Glucopyranosyl-|A-D-glucopyranoside;SY009512;FT-0600041;FT-0622099;FT-0632446;EN300-19821;Z104475610;87F82840-8E16-44B0-BF95-F1CBF910BF92;2-(Hydroxymethyl)-6-([3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl]oxy)tetrahydro-2h-pyran-3,4,5-triol

Chemical Property of alpha-D-Glucopyranoside, alpha-D-glucopyranosyl

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Vapor Pressure: 3.87E-21mmHg at 25°C
• Melting Point: 203 °C
• Refractive Index: 197 ° (C=7, H2O)
• Boiling Point: 675.384 °C at 760 mmHg
• PKA: 12.53±0.70(Predicted)
• Flash Point: 362.259 °C
• PSA: 189.53000
• Density: 1.768 g/cm³
• LogP: -5.39720
• Storage Temp.: Inert atmosphere,Room Temperature
• Sensitive.: Hygroscopic
• Solubility.: Soluble in water; very slightly soluble in ethanol (95%); practically insoluble in ether.
• Water Solubility.: Soluble in water.
• XLogP3: -4.2
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 342.11621151
• Heavy Atom Count: 23
• Complexity: 348

Purity/Quality:

99% ^*data from raw suppliers

D-Trehalose ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(C1C(C(C(C(O1)OC2C(C(C(C(O2)CO)O)O)O)O)O)O)O
• Description: Trehalose is a nonreducing disaccharide in which the two glucose molecules are linked together in an α,α-1,1-glycosidic linkage. α,α-trehalose is the only anomer of trehalose, which has been isolated from and biosynthesized in living organisms. This sugar is present in a wide variety of organisms, including bacteria, yeast, fungi, insects, invertebrates, and lower and higher plants, where it may serve as a source of energy and carbon.? It can be used as a stabilizer and protectant of proteins and membranes: protection from dehydration; protection from damage by oxygen radicals (against oxidation); protection from cold; as a sensing compound and/or growth regulator; as a structural component of the bacterial cell wall. Trehalose is used in the biopharmaceutical preservation of labile protein drugs and in the cryopreservation of human cells. It is used as an ingredient for dried and processed food, and as an artificial sweetener, with a relative sweetness of 40-45% that of sucrose. Several safety studies on trehalose have been evaluated by JECFA, 2001 and allocated an ADI of ‘not specified’. Trehalose is approved in Japan, Korea, Taiwan, and UK. Trehalose could be possibly used in an eye drop solution to against corneal damage due to desiccation (dry eye syndrome).
• Uses: trehalose is a humectant and moisturizer, it helps bind water in the skin and increase the skin’s moisture content. It is a naturally occurring plant sugar. D-(+)-Trehalose can be used for the effects of sucrose on blood avidity in mosquitoes.

Technology Process of alpha-D-Glucopyranoside, alpha-D-glucopyranosyl

There total 39 articles about alpha-D-Glucopyranoside, alpha-D-glucopyranosyl which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

4,6;4',6'-di-O-benzylidene-α,α-D-trehalose (18929-82-3,60949-45-3,97390-02-8,127128-52-3) → TREHALOSE (99-20-7)

Guidance literature:

With methanol; toluene-4-sulfonic acid; at 20 ℃; for 0.0333333h; sonication;

DOI:10.1021/jo060374w

Reference yield: 95.0%

(2R,3R,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol (615564-31-3) → TREHALOSE (99-20-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 24h;

DOI:10.1021/ol034836t

Reference yield:

adenosine-5'-(α-D-glucopyranosyl)diphosphate (2140-58-1) + D-glucose (50-99-7) → TREHALOSE (99-20-7) + adenosine 5'-diphosphate (58-64-0,905904-58-7)

Guidance literature:

With Pyrococcus horikoshii trehalose synthase; at 60 ℃; for 24h; pH=6; aq. acetate buffer; Enzymatic reaction;

DOI:10.1016/j.procbio.2010.07.030

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-glucopyranosyl-(1?1)-2,3,4,6-tetra-O-benzyl-D-glucopyranoside

alpha-D-glucopyranose

β-D-glucopyranosyl fluoride

D-Glucose

Downstream raw materials:

6-O-(triphenylmethyl)-α-D-glucopyranosyl-6'-O-(triphenylmethyl)-α-D-glucopyranoside

2',3',4',6'-Tetra-O-benzoyl-α-D-glucopyranosyl 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranoside

6,6'-di-O-palmitoyl-α,α-trehalose

2,3,4,6,2',3',4',6'-octa-O-trimethylsilyl-α,α-D-trehalose

Refernces

• 1、 Pe?a-Zalbidea, Santiago,Huang, Ashley Y.-T.,Kavunja, Herbert W.,Salinas, Beatriz,Desco, Manuel,Drake, Christopher,Woodruff, Peter J.,Vaquero, Juan J.,Swarts, Benjamin M.. "Chemoenzymatic radiosynthesis of 2-deoxy-2-[18F]fluoro-D-trehalose ([18F]-2-FDTre): A PET radioprobe for in vivo tracing of trehalose metabolism". . p. 16 - 22. Retrieved 2019.
• 2、 John, George,Zhu, Guangyu,Li, Jun,Dordick, Jonathan S.. "Enzymatically derived sugar-containing self-assembled organogels with nanostructured morphologies". . p. 4772 - 4775. Retrieved 2006.
• 3、 Kizawa,Miyazaki,Yokota,Kanegae,Miyagawa,Sugiyama. "Trehalose production by a strain of Micrococcus varians". . p. 1522 - 1527. Retrieved 1995.
• 4、 -. "COMPOSITIONS AND METHODS". . . Retrieved 2019/08/26.