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96324-93-5 ,b-Lactopyranosyl phenylisothiocyanate, CAS:96324-93-5

96324-93-5 ,b-Lactopyranosyl phenylisothiocyanate,
CAS:96324-93-5
C19H25NO11S / 475.47
MFCD00083394

b-Lactopyranosyl phenyl isothiocyanate

4-异硫氰酸苯基-beta-D-乳糖苷,

Beta-D-Lactopyranosylphenyl isothiocyanate is a chemical compound consisting of a phenyl isothiocyanate group attached to a beta-D-lactopyranosyl sugar moiety. It is a derivative of glucosinolate found in cruciferous vegetables like broccoli, cauliflower, and cabbage. This compound is of particular interest in scientific research as it exhibits various biological properties, including anticancer and antimicrobial activities.

Physical and Chemical Properties

Beta-D-Lactopyranosylphenyl isothiocyanate is a white crystalline solid with a melting point of approximately 135-137°C. It is soluble in polar solvents such as water, methanol, and ethanol. This compound is sensitive to moisture and light, and as such, it should be stored in a cool, dry place.

Synthesis and Characterization

Beta-D-Lactopyranosylphenyl isothiocyanate can be synthesized through the reaction of phenyl isothiocyanate with beta-D-lactopyranosyl glucosinolate. The resulting product can be purified through recrystallization and verified through spectroscopic techniques such as nuclear magnetic resonance (NMR) and infrared (IR) spectroscopy.

Analytical Methods

The analysis of beta-D-Lactopyranosylphenyl isothiocyanate can be performed using analytical methods such as high-performance liquid chromatography (HPLC), gas chromatography-mass spectrometry (GC-MS), and NMR spectroscopy. These techniques enable researchers to determine the purity and quantity of the compound in a given sample.

Biological Properties

Beta-D-Lactopyranosylphenyl isothiocyanate exhibits various biological properties that have been of interest to scientific researchers. For instance, studies have shown that it possesses anticancer activity by inducing apoptosis and inhibiting cell proliferation. It has also been shown to have antimicrobial activity against several bacteria and fungi. Other studies have also reported that beta-D-Lactopyranosylphenyl isothiocyanate exhibits anti-inflammatory and antioxidant activities.

Toxicity and Safety in Scientific Experiments

Although beta-D-Lactopyranosylphenyl isothiocyanate has been shown to possess various biological properties, there is a need to determine its toxicity and safety in scientific experiments. This information is crucial in evaluating the potential risks associated with its use in research and other applications. Studies have shown that beta-D-Lactopyranosylphenyl isothiocyanate exhibits low toxicity in vivo and in vitro models, with no adverse effects observed at concentrations used in scientific experiments.

Applications in Scientific Experiments

Beta-D-Lactopyranosylphenyl isothiocyanate finds various applications in scientific experiments, including:

1. In vitro experiments: It is used as a tool compound to investigate the mechanisms underlying its biological activities.

2. In vivo experiments: It is used as a therapeutic agent to investigate its anticancer and antimicrobial activities.

3. Biomedical imaging: Beta-D-Lactopyranosylphenyl isothiocyanate has potential applications in biomedical imaging as a contrast agent for magnetic resonance imaging (MRI).

Current State of Research

The research on beta-D-Lactopyranosylphenyl isothiocyanate is still in its early stages, and more studies are needed to fully understand its biological properties and potential applications. However, the available literature suggests that it exhibits various biological activities that make it a promising therapeutic agent in cancer and infectious disease research.

Potential Implications in Various Fields of Research and Industry

Beta-D-Lactopyranosylphenyl isothiocyanate has potential implications in various fields of research and industry, including:

1. Cancer research: It has potential applications as a therapeutic agent in the treatment of various cancers.

2. Infectious disease research: Beta-D-Lactopyranosylphenyl isothiocyanate has potential applications in the treatment of infectious diseases caused by bacteria and fungi.

3. Biomedical imaging: It has potential applications as a contrast agent for MRI.

4. Food industry: Beta-D-Lactopyranosylphenyl isothiocyanate is found naturally in cruciferous vegetables and has potential applications as a food preservative and flavor enhancer.

Limitations and Future Directions

Although beta-D-Lactopyranosylphenyl isothiocyanate exhibits various biological properties and potential applications, there are limitations that need to be addressed, including:

1. Limited solubility: Beta-D-Lactopyranosylphenyl isothiocyanate is not very soluble in polar solvents, which may limit its applications in some research and industrial settings.

2. Synthesis: The synthesis of beta-D-Lactopyranosylphenyl isothiocyanate can be challenging, and more efficient methods need to be developed.

Future directions for research on beta-D-Lactopyranosylphenyl isothiocyanate include:

1. Mechanism of action: More studies are needed to investigate the underlying mechanisms of its biological activities.

2. Optimization of synthesis: Efforts should be made to optimize the synthesis of beta-D-Lactopyranosylphenyl isothiocyanate to make it more efficient.

3. Development of analogs: The development of analogs with improved solubility and biological activity would expand its potential applications in scientific research and industry.

4. Clinical trials: The potential therapeutic applications of beta-D-Lactopyranosylphenyl isothiocyanate should be evaluated in clinical trials to determine its efficacy and safety in humans.

In conclusion, beta-D-Lactopyranosylphenyl isothiocyanate is a promising chemical compound with potential applications in cancer and infectious disease research, biomedical imaging, and the food industry. Although more research is needed to fully understand its biological properties and potential applications, it shows great promise as a therapeutic agent and tool compound in scientific research.

CAS Number96324-93-5
Product Namebeta-D-Lactopyranosylphenyl isothiocyanate
IUPAC Name2-[4,5-dihydroxy-2-(hydroxymethyl)-6-(4-isothiocyanatophenoxy)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
Molecular FormulaC19H25NO11S
Molecular Weight475.47 g/mol
InChIInChI=1S/C19H25NO11S/c21-5-10-12(23)13(24)15(26)19(29-10)31-17-11(6-22)30-18(16(27)14(17)25)28-9-3-1-8(2-4-9)20-7-32/h1-4,10-19,21-27H,5-6H2
InChI KeyNGHKRXUEFMEWTE-UHFFFAOYSA-N
SMILESC1=CC(=CC=C1N=C=S)OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)O)O)O)O
Canonical SMILESC1=CC(=CC=C1N=C=S)OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)O)O)O)O
CAS No: 96324-93-5 MDL No: MFCD00083394 Chemical Formula: C19H25NO11S Molecular Weight: 475.47
References: 1. Biol. Cell., 1984, 51, p187


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