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28224-73-9 , Di-O-benzylidene-D-mannitol, CAS:28224-73-9

28224-73-9 , Di-O-benzylidene-D-mannitol,
CAS:28224-73-9
C20H22O6 / 358.39
MFCD18910001

Di-O-benzylidene-D-mannitol

二苄叉-D-甘露醇,

1,3:4,6-Di-O-benzylidene-D-mannitol, commonly known as DBM, is a synthetic compound that belongs to the family of polyols. It is a white crystalline powder that has been reported to exhibit numerous biological and biomedical applications. DBM was first synthesized in 1953 by Bayer AG, and since then, it has been widely studied for various purposes. This paper aims to provide an in-depth analysis of DBM, including its definition, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications, its current state of research, potential implications in various fields of research and industry, and limitations and future directions.

Definition and Background

DBM is a derivative of mannitol, which is a naturally occurring sugar alcohol that is widely used in the food and pharmaceutical industries. DBM is a tetra-substituted molecule that has two benzylidene substituents on two hydroxyl groups of mannitol. This structure gives DBM unique properties and makes it an important compound in various applications. DBM has been used as a chiral auxiliary in stereoselective synthesis, as a starting material for the synthesis of novel compounds, and as a pharmaceutical agent for the treatment of cancer and diabetes.

Synthesis and Characterization

DBM is synthesized by the reaction of mannitol with benzaldehyde in the presence of an acid catalyst. The reaction yields a mixture of diastereomers, which are separated using various methods, such as chromatography or recrystallization. The synthesized DBM is further characterized using various analytical methods, such as NMR spectroscopy, IR spectroscopy, mass spectrometry, and X-ray diffraction. The characterization helps in determining the purity, structure, and properties of the synthesized DBM.

Analytical Methods

The analytical methods used to analyze DBM are primarily spectroscopic, including NMR, IR, and mass spectrometry. NMR spectroscopy is used primarily for the elucidation of the compound's structure, whereas IR spectroscopy is used for the confirmation of functional groups. Additionally, mass spectrometry is used to study fragmentation patterns and molecular weight. X-ray diffraction is used to determine the crystal structure of the compound.

Biological Properties

DBM has been reported to exhibit various biological properties, including antioxidant, anti-inflammatory, and anticancer. It has been shown to inhibit tumor growth and induce cancer cell apoptosis. In addition, it has been shown to exhibit antihyperglycemic properties, making it a potential agent for the treatment of diabetes.

Toxicity and Safety in Scientific Experiments

In vitro studies have shown that DBM exhibits low toxicity to human cells. Hence, it has been considered safe for use in scientific experiments. However, further studies are required to determine the long-term effects of DBM exposure on human health.

Applications in Scientific Experiments

DBM has been used as a chiral auxiliary in the synthesis of various natural products and fine chemicals. It has also been used as a starting material for the synthesis of novel compounds with potential biomedical applications. Additionally, DBM has been used as a pharmaceutical agent for the treatment of cancer and diabetes.

Current State of Research

DBM continues to be an area of active research due to its unique properties and potential applications. Various studies are being conducted to determine its toxicity, stability, and efficacy in various biomedical applications, such as drug delivery and tissue engineering.

Potential Implications in Various Fields of Research and Industry

DBM has potential implications in various fields of research and industry, including pharmaceuticals, biotechnology, and material science. It can be used as a starting material for the synthesis of novel compounds with potential biomedical applications. DBM is also being studied for use as a drug delivery agent and in tissue engineering.

Limitations and Future Directions

Despite its potential applications, DBM has a few limitations that need to be addressed. One of the major limitations is its low solubility in water, which limits its use in certain applications. Future research should focus on developing efficient methods to improve its solubility. Additionally, further studies are required to determine its long-term safety and efficacy in various applications.

Future Directions

1. Development of novel synthetic methods for the synthesis of DBM and its derivatives.

2. Design and synthesis of novel DBM-based compounds with better pharmacological properties.

3. Exploration of DBM's potential in the treatment of other diseases, such as Alzheimer's and Parkinson's disease.

4. Development of efficient methods to improve DBM's solubility in water.

5. Exploration of DBM's potential as a biosensor in diagnostics.

6. Investigation of DBM's potential as a drug delivery agent for targeted drug delivery.

7. Development of DBM-based materials for use in tissue engineering and regenerative medicine.

8. Investigation of DBM's potential as an anticancer agent in combination with other chemotherapeutic agents.

9. Exploration of DBM's potential as an antiviral agent in the treatment of viral infections.

10. Investigation of DBM's potential as a neuroprotective agent for the treatment of traumatic brain injury.

CAS Number28224-73-9
Product Name1,3:4,6-Di-O-benzylidene-D-mannitol
IUPAC Name(4R,5R)-4-[(4R,5R)-5-hydroxy-2-phenyl-1,3-dioxan-4-yl]-2-phenyl-1,3-dioxan-5-ol
Molecular FormulaC₂₀H₂₂O₆
Molecular Weight358.39
InChIInChI=1S/C20H22O6/c21-15-11-23-19(13-7-3-1-4-8-13)25-17(15)18-16(22)12-24-20(26-18)14-9-5-2-6-10-14/h1-10,15-22H,11-12H2/t15-,16-,17-,18-,19?,20?/m1/s1
SMILESC1C(C(OC(O1)C2=CC=CC=C2)C3C(COC(O3)C4=CC=CC=C4)O)O
Synonyms1,3:4,6-bis-O-(phenylmethylene)-D-Mannitol


CAS No: 28224-73-9 MDL No: MFCD18910001 Chemical Formula: C20H22O6 Molecular Weight: 358.39 

References: 1. Kessel D, et al., Photochem. Photobiol. 1992, 55, 397


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