1,7-Bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
[CAS# 36062-04-1]

Identification

• Classification: Natural product >> Natural phenols
• Name: 1,7-Bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione
• Synonyms: Tetrahydrocurcumin; Tetrahydrodiferuloylmethane
• Molecular Formula: C₂₁H₂₄O₆
• Molecular Weight: 372.41
• CAS Registry Number: 36062-04-1
• EC Number: 609-201-3
• SMILES: COC1=C(C=CC(=C1)CCC(=O)CC(=O)CCC2=CC(=C(C=C2)O)OC)O

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*, 1.222 g/mL (Expl.)
• Melting point: 95-97 °C (Expl.)
• Index of Refraction: 1.575, Calc.^*
• Boiling Point: 564.1±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 196.2±22.2 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Discovery and Applications

1,7-Bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione, commonly known for its molecular structure consisting of a heptane backbone with two 4-hydroxy-3-methoxyphenyl groups attached at positions 1 and 7, along with two keto groups at positions 3 and 5, is a compound of interest in organic chemistry and medicinal research. The compound is an example of a substituted chalcone derivative, where the phenyl groups are linked through a saturated heptane chain, each bearing hydroxyl and methoxy substituents at specific positions.

The discovery of this compound is rooted in the exploration of chalcone derivatives, which have been extensively studied for their diverse biological activities. Chalcones themselves are a class of compounds known for their wide range of biological properties, such as anti-inflammatory, antioxidant, antimicrobial, and anticancer effects. The modification of chalcones by adding various functional groups, such as hydroxyl and methoxy groups, has often been pursued to enhance or modulate these activities. In the case of 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione, the addition of the heptane backbone was likely aimed at improving the solubility and bioavailability of the compound, which is often a challenge with more rigid chalcone structures.

One of the primary applications of 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione is in medicinal chemistry, where it has been investigated for its potential pharmacological activities. The compound’s structure suggests that it may function as an antioxidant, given the presence of phenolic hydroxyl groups, which are known to confer antioxidant properties. These properties are of particular interest in the context of aging, neurodegenerative diseases, and conditions associated with oxidative stress, such as cardiovascular diseases.

Moreover, the methoxy groups attached to the phenyl rings contribute to the compound's potential to interact with biological targets, such as enzymes and receptors, and could enhance the compound’s ability to cross biological membranes. These functional groups may also alter the compound’s affinity for various molecular targets, making it a valuable lead compound for the design of new drug candidates.

In addition to its potential medicinal applications, 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione may also have uses in materials science. The compound's phenolic structure and ability to undergo various chemical reactions make it a useful intermediate in the synthesis of more complex molecules. For example, it may serve as a building block for the preparation of polymers or materials with specific electronic or optical properties. The conjugated system in the molecule, which is enhanced by the methoxy and hydroxyl substitutions, could allow for applications in fields such as organic electronics or optoelectronics, where chalcone derivatives have shown promise as organic semiconductors.

Furthermore, 1,7-bis(4-hydroxy-3-methoxyphenyl)heptane-3,5-dione may serve as a potential scaffold for the development of herbicides or pesticides. The ability of chalcone derivatives to interact with biological systems has been explored for their role in controlling plant growth or inhibiting specific enzymes involved in metabolic processes in pests. In this regard, the compound could be of interest in the agricultural industry as a starting material for the development of environmentally friendly pest control agents.

References

2020. Curcumin Analogs in Medicinal Chemistry. Bioorganic Chemistry, 103.
DOI: 10.1016/j.bioorg.2020.104234