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A1269

Sigma-Aldrich

4-Aminophenyl β-D-glucopyranoside

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About This Item

Empirical Formula (Hill Notation):
C12H17NO6
CAS Number:
20818-25-1
Molecular Weight:
271.27
MDL number:
MFCD00067365
UNSPSC Code:
12352201
PubChem Substance ID:
24890520
NACRES:
NA.25

Assay

≥98% (TLC)

Quality Level

200

form

powder

optical activity

[α]/D -65.00 to -59.00°, c = 9.00-11.00 mg/mL in water

technique(s)

thin layer chromatography (TLC): suitable

solubility

water: 49.00-51.00 mg/mL, clear to slightly hazy, colorless to light yellow

storage temp.

−20°C

SMILES string

Nc1ccc(OC2OC(CO)C(O)C(O)C2O)cc1

InChI

1S/C12H17NO6/c13-6-1-3-7(4-2-6)18-12-11(17)10(16)9(15)8(5-14)19-12/h1-4,8-12,14-17H,5,13H2

InChI key

MIAKOEWBCMPCQR-UHFFFAOYSA-N

Application

P-Aminophenyl β-D-glucopyranoside is used to create derivitized agarose beads useful for the analysis of the surfaces of cancer cells. 4-Aminophenyl β-D-glucopyranoside is used to derivatize biocompatible single-crystalline gold tabular nanoparticles, nanoprisms (NPRs) to improve their stability and cellular uptake.

Other Notes

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

监管及禁止进口产品

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Certificates of Analysis (COA)

Lot/Batch Number
0000112142
0000096929
039M4120V
13181140
076M4132V

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Beatriz Pelaz et al.
Langmuir : the ACS journal of surfaces and colloids, 28(24), 8965-8970 (2012-01-21)
The paper describes a novel and straightforward wet-chemical synthetic route to produce biocompatible single-crystalline gold tabular nanoparticles, herein called nanoprisms (NPRs) due to their characteristic shape. Besides the novelty of the method to produce NPRs with an unprecedented high yield
Zhirui Guo et al.
Journal of colloid and interface science, 348(1), 29-36 (2010-05-21)
Gold nanoprisms with average edge size of approximately 140 nm and thickness of approximately 8 nm were achieved in high-purity ( approximately 97%) by exploiting the electrostatic aggregation and shape effects through a modified seed-mediated approach. The proposed strategy lies
Reductive syntheses of p-aminophenyl-beta-D-glucoside and its conversion to beta-glucosyl Yariv reagent.
I Ganjian et al.
Analytical biochemistry, 246(1), 152-155 (1997-03-01)
M Naoi et al.
Journal of neurochemistry, 50(4), 1297-1301 (1988-04-01)
Rat clonal pheochromocytoma PC12h cells were found to bind beta-galactosidase modified with specific glycosides. The enzyme modified with p-aminophenyl beta-D-glucoside was most effectively bound to the cells, followed by alpha-D-mannoside and alpha-D-glucoside. The binding was dependent on the number of
Maria R Khurrum et al.
Acta histochemica, 104(3), 217-223 (2002-10-23)
Standard histochemical analysis of cells and tissues generally involves procedures that utilize a relatively small number of probes such as dyes, and generally requires hours or days to process. Our laboratory has developed a novel method for histochemical surveys of
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