D-glycero-D-gulo-Heptonic acid, γ-lactone

D-glycero-D-gulo-Heptonic acid, γ-lactone

D-glycero-D-gulo-Heptonic acid, γ-lactone (CAS No. 89-67-8) is a seven-carbon sugar lactone that plays a significant role in organic chemistry and biochemistry. This compound is notable for its applications as a precursor in various synthetic pathways and its potential biological activities.

Chemical and Physical Properties

• CAS Number: 89-67-8
• MDL Number: MFCD00005390
• EINECS: 201-929-6
• Molecular Formula: C₇H₁₂O₇
• Molecular Weight: 208.17 g/mol
• Boiling Point: Not specified (predicted to be around 557.5°C)
• Melting Point: 148–149°C
• Density: 1.806 ± 0.06 g/cm³ at 20°C (760 Torr)
• Appearance: Typically a white to off-white crystalline solid

Structure and Composition

D-glycero-D-gulo-heptonic acid, γ-lactone features a cyclic structure formed by the esterification of a hydroxyl group with a carbonyl group. The lactone ring contributes to its stability and reactivity, making it an important intermediate in organic synthesis.

Biological Activity and Applications

1. Synthetic Precursor: This compound serves as a key intermediate in the synthesis of various organic molecules, particularly in the production of complex carbohydrates and other biologically active compounds.
2. Research Applications: D-glycero-D-gulo-heptonic acid, γ-lactone is utilized in biochemical research to study carbohydrate metabolism and the synthesis of glycosylated compounds.
3. Potential Health Benefits: While specific health benefits are not widely documented, compounds like D-glycero-D-gulo-heptonic acid may exhibit biological activities that warrant further investigation.

Synthesis Methods

The synthesis of D-glycero-D-gulo-heptonic acid, γ-lactone typically involves the oxidation of D-glycero-D-gulo-heptose using oxidizing agents such as bromine or iodine in the presence of a base. Careful control of reaction conditions is essential to optimize yield and purity.

Safety and Handling

D-glycero-D-gulo-heptonic acid, γ-lactone is generally considered safe for use in laboratory settings; however, standard safety protocols should be adhered to when handling this compound to prevent exposure.

Storage Recommendations

For long-term stability, store D-glycero-D-gulo-heptonic acid, γ-lactone at temperatures between 2–8°C in a cool, dry place away from light.

In summary, D-glycero-D-gulo-heptonic acid, γ-lactone is an important carbohydrate derivative with significant applications in organic synthesis and potential biological relevance.

Citations:

1. https://www.evitachem.com/product/evt-297433
2. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8905284.htm
3. https://pubchem.ncbi.nlm.nih.gov/compound/102367
4. https://pubchem.ncbi.nlm.nih.gov/compound/D-Glycero-L-manno-heptono-gamma-lactone
5. https://webbook.nist.gov/cgi/cbook.cgi?ID=C89678&Units=SI
6. https://www.chemsrc.com/en/cas/87-74-1_890940.html
7. https://www.chemeo.com/cid/60-134-6/D-glycero-D-gulo-Heptonic-acid-gamma-lactone
8. https://www.chemsrc.com/en/cas/15397-07-6_1536313.html