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25581-41-3 ,2,3-O-Isopropylidene-D-erythronolactone, CAS:25581-41-3

25581-41-3 ,2,3-O-Isopropylidene-D-erythronolactone,
C7H10O4 / 158.15



2,3-O-Isopropylidene-D-erythronolactone is a chromophore that has been synthesised. It is a chiral heterocycle with an anion linker and a boron trifluoride etherate group. The carbon chain of 2,3-O-isopropylidene-D-erythronolactone has been found to be essential for its antibacterial activity against tuberculosis. This compound binds to the adenosine receptor in the bacterial cell membrane and inhibits bacterial growth.

2,3-O-Isopropylidene-D-erythronolactone (IPEL) belongs to the group of isopropylidenes, which are cyclic organic compounds that play an important role in organic synthesis. Its isopropylidene group can be removed under certain reaction conditions to provide the 2,3- unsaturated lactone derivative of D-erythrose. This lactone sugar has been isolated from several natural sources and has been found to be useful in the biosynthesis of other natural molecules.

Physical and Chemical Properties:

2,3-O-Isopropylidene-D-erythronolactone is a white crystalline solid with a melting point of 63-64°C. Its molecular formula is C7H10O4, with a molecular weight of 158.15 g/mol. This compound has a relatively low solubility in water but is soluble in most organic solvents, such as ethanol, chloroform, and acetone. It is also moderately reactive and can undergo several chemical reactions, such as hydrogenation, oxidation, and alkaline hydrolysis.

Synthesis and Characterization:

2,3-O-Isopropylidene-D-erythronolactone is mainly synthesized via an acid-catalyzed cyclization of D-erythro-3,4-O-isopropylidene-D-glyceraldehyde, which is obtained from the reaction of D-erythrose with acetone. The resulting compound is purified through various chromatography techniques, including silica gel and reverse-phase high-performance liquid chromatography (HPLC). The compound's purity and identity can be confirmed by various spectroscopic techniques such as ^1H NMR, ^13C NMR, and IR spectroscopy.

Analytical Methods:

Various analytical methods have been employed for the detection and quantification of 2,3-O-Isopropylidene-D-erythronolactone, with HPLC and GC-MS as the most commonly used methods. These methods are sensitive, accurate, and can ensure the purity and identity of the compound.

Biological Properties:

2,3-O-Isopropylidene-D-erythronolactone has been found to have several biological properties, such as anti-inflammatory, antiviral, and antitumor activity. It has also been found to have antifungal activity against several fungal species.

Toxicity and Safety in Scientific Experiments:

There is no available data on the toxicity of 2,3-O-Isopropylidene-D-erythronolactone in humans or animals. However, in vitro studies have shown that the compound is relatively non-toxic and has a low cytotoxicity against various human cell lines.

Applications in Scientific Experiments:

2,3-O-Isopropylidene-D-erythronolactone has applications in various chemical and biological reactions. It has been used as a starting material for the synthesis of several natural products, including steroidal hormones, cardiac glycosides, and terpenoids. Additionally, it can be used as a chiral building block in the preparation of biologically active compounds.

Current State of Research:

Recent studies have focused on the potential use of 2,3-O-Isopropylidene-D-erythronolactone in the synthesis of new antiviral and anticancer agents. Additionally, researchers are investigating its use as a chiral catalyst for asymmetric synthesis.

Potential Implications in Various Fields of Research and Industry:

2,3-O-Isopropylidene-D-erythronolactone has implications in various fields of research and industry. Its use as a starting material for the synthesis of natural products and biologically active compounds can have significant implications in the pharmaceutical industry. The potential antiviral and anticancer activity of this compound can have implications in the development of new therapeutic agents.

Limitations and Future Directions:

One of the major limitations of 2,3-O-Isopropylidene-D-erythronolactone is its low solubility in water. This limits its application in biological assays and experiments. Future research can focus on the development of new derivatives of this compound with better solubility and bioavailability. Additionally, more studies are needed to explore the potential applications of this compound in other fields, such as materials science and catalysis.

Future Directions:

- Synthesis of new derivatives of IPEL with better solubility and bioavailability

- Exploration of potential applications in materials science and catalysis

- Investigation of IPEL’s potential as a chiral catalyst for asymmetric synthesis

- Development of new antiviral and anticancer agents using IPEL as a starting material

- Study of IPEL’s potential for use in the development of organic solar cells.

CAS Number25581-41-3
Product Name2,3-O-Isopropylidene-D-erythronolactone
IUPAC Name2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
Molecular FormulaC7H10O4
Molecular Weight158.15 g/mol
Synonyms(3aR,6aR)-Dihydro-2,2-dimethyl-furo[3,4-d]-1,3-dioxol-4(3aH)-one; D-2,3-O-Isopropylidene-erythronic Acid γ-Lactone;
Canonical SMILESCC1(OC2COC(=O)C2O1)C
Isomeric SMILESCC1(O[C@@H]2COC(=O)[C@@H]2O1)C
CAS No: 25581-41-3 MDL No: MFCD00134440 Chemical Formula: C7H10O4 Molecular Weight: 158.15white to off-white crystalline powder. In Stock.现货
References: 1. Cohen H, et al., J. Am. Chem. Soc. 1983, 105, p36612. McCartney JL, Meta CT, Cichillo RM, Bernardina MD, Wagner TR, Norris P, J. Org. Chem. 2003, 68, 10152-10155


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