Genistein
[CAS# 446-72-0]

Identification

• Classification: Biochemical >> Natural biochemical product
• Name: Genistein
• Synonyms: 4',5,7-Trihydroxyisoflavone
• Molecular Formula: C₁₅H₁₀O₅
• Molecular Weight: 270.24
• CAS Registry Number: 446-72-0
• EC Number: 207-174-9
• SMILES: C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O

Properties

• Water solubility: insoluble (Expl.)
• Density: 1.5±0.1 g/cm³, Calc.^*
• Melting point: 297-298 °C (Expl.)
• Index of Refraction: 1.732, Calc.^*
• Boiling Point: 555.5±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 217.1±23.6 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07;GHS09 Warning
• Risk Statements: H302-H315-H319-H335-H400-H410
• Safety Statements: P261-P264-P264+P265-P270-P271-P273-P280-P301+P317-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P391-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Acute toxicity	Acute Tox.	4	H302
Skin irritation	Skin Irrit.	2	H315
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400
Eye irritation	Eye Irrit.	2	H319
Reproductive toxicity	Repr.	2	H361
Germ cell mutagenicity	Muta.	2	H341
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

Genistein is a naturally occurring isoflavonoid, predominantly found in soybeans, and recognized for its potential health benefits. Structurally, it is a 5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one, belonging to the class of compounds known as phytoestrogens due to its ability to mimic estrogen in the body. The compound is primarily known for its antioxidant, anti-inflammatory, and anticancer properties, which have made it the subject of extensive research in both pharmacology and nutrition.

The discovery of genistein dates back to the early 20th century when it was first isolated from soybean in the 1930s. It was identified as one of the primary isoflavones in soybeans, contributing to the health-promoting effects of soy consumption. Over the decades, scientists have progressively elucidated its chemical structure and biological activity, leading to a better understanding of its role in human health. In particular, genistein has garnered attention due to its estrogenic effects, which are attributed to its structural similarity to the hormone estrogen.

Genistein has been studied extensively for its potential in preventing and treating a range of health conditions. One of the most widely researched areas of application is in the context of cancer prevention. Studies have shown that genistein can inhibit the growth of cancer cells, particularly in breast, prostate, and colon cancers, by modulating cell cycle progression, inducing apoptosis (programmed cell death), and interfering with angiogenesis (the formation of new blood vessels). This makes genistein a promising candidate for cancer chemoprevention or as an adjunct to traditional cancer therapies. Its antioxidant properties, which help neutralize free radicals and reduce oxidative stress, also contribute to its anticancer effects.

In addition to its anticancer properties, genistein has been explored for its potential role in promoting cardiovascular health. By modulating lipid metabolism, reducing blood pressure, and improving endothelial function, genistein may help reduce the risk of heart disease. Some studies suggest that genistein’s ability to influence lipid profiles and enhance nitric oxide production can improve blood vessel health, potentially offering protection against atherosclerosis and other cardiovascular conditions.

Genistein's effects on bone health have also been a focus of research. As a phytoestrogen, genistein has the ability to bind to estrogen receptors in bone cells, which may help maintain bone density and reduce the risk of osteoporosis, particularly in postmenopausal women. Some studies have found that genistein supplementation can positively influence bone metabolism, suggesting its potential as a natural alternative to hormone replacement therapy in managing bone health.

The compound is also known for its neuroprotective properties. Genistein's ability to cross the blood-brain barrier and its effects on brain function have been investigated in the context of neurodegenerative diseases such as Alzheimer's disease. It has been suggested that genistein may protect neurons from damage induced by oxidative stress, inflammation, and amyloid plaque accumulation, which are hallmark features of Alzheimer's pathology.

Furthermore, genistein is being studied for its potential in managing menopausal symptoms. Its estrogenic effects may help alleviate symptoms such as hot flashes, mood swings, and vaginal dryness, providing an alternative to synthetic estrogen therapies for women experiencing menopause.

In terms of industrial applications, genistein is increasingly incorporated into dietary supplements, functional foods, and cosmetics. Its antioxidant and anti-inflammatory properties make it a valuable ingredient in skincare products aimed at reducing signs of aging and protecting the skin from environmental stressors. Genistein’s use in food products, particularly in soy-based products, has also been promoted due to its health benefits.

Despite its potential, genistein’s effects are still under investigation, with ongoing studies examining its long-term impact and optimal dosages for therapeutic use. As more clinical data become available, it is expected that genistein will play an increasingly significant role in health maintenance and disease prevention, especially for conditions influenced by estrogen and oxidative stress.

References

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

1991. Synthesis and protein-tyrosine kinase inhibitory activities of flavonoid analogues. Journal of Medicinal Chemistry, 34(2).
DOI: 10.1021/jm00106a047

1998. In vivo toxicity and pharmacokinetic features of B43 (anti-CD19)-genistein immunoconjugate in nonhuman primates. Clinical Cancer Research, 4(1).
URL: https://pubmed.ncbi.nlm.nih.gov/9516966