Isoflavone
[CAS# 574-12-9]

Identification

• Classification: Biochemical >> Plant extracts
• Name: Isoflavone
• Synonyms: 3-Phenylchromen-4-one; 3-Phenyl-4H-1-benzopyran-4-one
• Molecular Formula: C₁₅H₁₀O₂
• Molecular Weight: 222.24
• CAS Registry Number: 574-12-9
• EC Number: 611-522-9
• SMILES: C1=CC=C(C=C1)C2=COC3=CC=CC=C3C2=O

Properties

• Solubility: Soluble (Chloroform )
• Melting point: 132.5-133.5 °C

Safety Data

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

Discovery and Applications

Isoflavones are naturally occurring organic compounds that belong to the class of flavonoids found in a variety of plants, with soybeans being one of the richest sources. Isoflavones are well known for their potential health benefits, including antioxidant, anti-inflammatory, and estrogenic activity.

Isoflavones were first discovered in the early 20th century. In 1926, chemist J.B. Harborne discovered the isoflavone genistein in soybean plants. This discovery opened the door to research on isoflavones and their important role in plant and human health. Further research has led to the discovery of other important isoflavones, such as daidzein and glycitein, which are primarily found in beans.

The basic chemical structure of isoflavones is similar to that of estrogen, which allows them to bind to estrogen receptors in the body. Its molecular formula, C15H10O2, is the basic isoflavone structure, which is soluble in organic solvents such as ethanol and methanol and is usually solid at room temperature

Isoflavones play a variety of key roles in plant and human health:Isoflavones act as phytoestrogens, which are plant-derived compounds with estrogenic activity. They can mimic or regulate estrogen in the body, affecting a variety of physiological processes. Isoflavones have antioxidant properties that help neutralize harmful free radicals and reduce cellular oxidative stress. Isoflavones have antimicrobial properties that protect plants from pathogens.

Isoflavones have received much attention for their potential health benefits. Because of their estrogen-like effects, isoflavones are used as a natural alternative to hormone replacement therapy (HRT) for the treatment of menopausal symptoms. Isoflavones can help improve heart health by lowering cholesterol levels, improving arterial flexibility, and providing anti-inflammatory effects. They promote bone health by increasing bone density and reducing the risk of osteoporosis, especially in postmenopausal women. Some studies suggest that isoflavones may reduce the risk of certain cancers, such as breast and prostate cancer, due to their ability to regulate estrogen metabolism and exert antioxidant effects.

Isoflavones are often included in nutraceuticals and dietary supplements, usually from soy extracts. These supplements have potential for overall health, especially for women experiencing menopausal symptoms.

Isoflavones occur naturally in a variety of foods, especially soy products such as tofu, tempeh, and soy milk. Inclusion of isoflavone-rich foods in the diet is encouraged due to their potential health benefits.

Isoflavones are used in skin care and cosmetics for their anti-aging and antioxidant properties. They help protect the skin from environmental damage and may improve skin elasticity and moisturization.

Isoflavones play a role in plant defense mechanisms against pests and diseases. They are also involved in nitrogen fixation in legumes, contributing to soil fertility and sustainable agriculture.

Isoflavones are naturally occurring compounds in foods that have been consumed by people for centuries and are a safe and well-tolerated health-promoting option. Isoflavones exhibit a wide range of biological activities and are used in a variety of applications, from healthcare and nutrition to cosmetics and agriculture. Isoflavones promote sustainable agricultural practices through their roles in nitrogen fixation and plant defense, promoting healthier crop production and reducing the need for chemical inputs.

References

2000. Soyfoods and soybean phyto-oestrogens (isoflavones) as possible alternatives to hormone replacement therapy (HRT). European journal of cancer (Oxford, England : 1990), 36.
DOI: 10.1016/s0959-8049(00)00233-1

1979. Isoflavones and hypercholesterolemia in rats. Lipids, 14(6).
DOI: 10.1007/bf02533528

1979. Antineoplastic Activity and Cytotoxicity of Flavones, Isoflavones, and Flavanones. Journal of Natural Products, 42(1).
DOI: 10.1021/np50001a002