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14152-97-7, GITC, 2,3,4,6-tetra-o-acetyl-glucopyranosyl isothiocyanate, CAS:14152-97-7

14152-97-7, GITC, 2,3,4,6-tetra-o-acetylglucopyranosylisothiocyanate,
CAS:14152-97-7
C15H19NO9S / 389.38
MFCD00043085

2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl isothiocyanate

GITC ,2,3,4,6-四乙酰基-BATA-D-葡萄糖异硫氰酸酯

2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl isothiocyanate (TGIT) is a compound that mimics the melanoma antigen. It has been used to identify human pathogens in biological samples and has shown to have an antibody response. TGIT has also been used as a fluorescent probe for nucleic acids in analytical methods and polymerase chain reaction. This chemical can be used as a fluorescence detector in titration calorimetry. TGIT is not acutely toxic, but can cause cell lysis when combined with trifluoroacetic acid.

2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate, also known as GlcNITC, is a chemical compound that is derived from the reaction between glucosamine and allyl isothiocyanate.

Synthesis and Characterization:

GlcNITC can be synthesized by reacting glucosamine with allyl isothiocyanate. The reaction is generally carried out in the presence of a base. The compound can be characterized using various analytical techniques such as Nuclear Magnetic Resonance (NMR) spectroscopy, infrared spectroscopy (IR), and mass spectrometry (MS).

Analytical Methods:

GlcNITC can be analyzed using various analytical techniques such as HPLC, TLC, and GC. The compound can also be quantified using spectrophotometric methods.

Biological Properties:

Studies have shown that GlcNITC has anti-inflammatory, anti-tumor, and anti-oxidant properties. It has been reported to induce cell cycle arrest and apoptosis in cancer cells.

Toxicity and Safety in Scientific Experiments:

Studies have shown that GlcNITC is relatively non-toxic and safe for use in scientific experiments. However, it is recommended to use the compound in a well-ventilated area and with appropriate personal protective equipment.

Applications in Scientific Experiments:

GlcNITC has been used in various scientific experiments as a chemical probe to study biological processes such as glycosylation and glycation. It has also been used as a fluorescent probe to study protein-protein interactions.

Current State of Research:

Research on GlcNITC is still in its early stages. However, several studies have shown promising results in the development of new therapeutic agents against cancer.

Potential Implications in Various Fields of Research and Industry:

GlcNITC has potential applications in the fields of biotechnology, pharmacology, and medicinal chemistry. The compound could also have implications in the development of new drugs for cancer treatment.

Limitations and Future Directions:

The limitations of GlcNITC include its low solubility in non-polar solvents and its relatively low potency as an anti-tumor agent. Future directions for research include the development of new synthetic methods for GlcNITC, the characterization of its binding sites on target proteins, and the evaluation of its efficacy in animal models of cancer.

Future Directions:

- Development of GlcNITC prodrugs to improve solubility and bioavailability.

- Evaluation of GlcNITC in combination with other anti-cancer agents to enhance its therapeutic potential.

- Investigation of the mechanism of action of GlcNITC in cancer cells.

- Development of GlcNITC derivatives with improved potency and selectivity.

- Evaluation of GlcNITC in animal models of cancer metastasis.

CAS Number14152-97-7
Product Name2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate
IUPAC Name(3,4,5-triacetyloxy-6-isothiocyanatooxan-2-yl)methyl acetate
Molecular FormulaC15H19NO9S
Molecular Weight389.38 g/mol
InChIInChI=1S/C15H19NO9S/c1-7(17)21-5-11-12(22-8(2)18)13(23-9(3)19)14(24-10(4)20)15(25-11)16-6-26/h11-15H,5H2,1-4H3
InChI KeyWOWNQYXIQWQJRJ-UXXRCYHCSA-N
SMILESCC(=O)OCC1C(C(C(C(O1)N=C=S)OC(=O)C)OC(=O)C)OC(=O)C
Synonyms2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate, 2,3,4,6-tetra-O-acetylglucopyranosylisothiocyanate, 2,3,4,6-tetra-O-acetylglucopyranosylisothiocyanate, (D)-isomer, GITC, TAGIT
Canonical SMILESCC(=O)OCC1C(C(C(C(O1)N=C=S)OC(=O)C)OC(=O)C)OC(=O)C
Isomeric SMILESCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)N=C=S)OC(=O)C)OC(=O)C)OC(=O)C


CAS No: 14152-97-7 MDL No: MFCD00043085 Chemical Formula: C15H19NO9S Molecular Weight: 389.38

COA:

Product name: 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate

CAS: 14152-97-7                         M.F.: C15H19NO9S                   M.W.: 389.38

Items

Standards

Results

Appearance

White crystalline power

Positive

Solubility

Readily soluble in CHCl3and

insoluble in water

Positive

NMR and MS

Should comply

Complies

Identification

IR and HPLC

Positive

M.P.

111  –115 

112  –114 

Specific rotation

+3.8°  to  +4.2°

+4.1°

Loss Weight On Dryness

Max. 1%

Complies

TLC

One spot

Complies

Water

Max. 0.5%

Complies

Assay by TLC

Min. 98%

99.2%

References:

1. Kinoshita T, et al., J. Chromatogr. 1980, 202, 375
2. Beil. 18, V, 1153

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