(E)-2-(1-Methylethyl)-5-(2-phenylethenyl)-1,3-benzenediol
[CAS# 79338-84-4]

Identification

• Classification: API >> Antipyretic analgesics >> Non-steroidal anti-inflammatory drugs
• Name: (E)-2-(1-Methylethyl)-5-(2-phenylethenyl)-1,3-benzenediol
• Synonyms: 5-[(E)-2-phenylethenyl]-2-propan-2-ylbenzene-1,3-diol
• Molecular Formula: C₁₇H₁₈O₂
• Molecular Weight: 254.32
• CAS Registry Number: 79338-84-4
• EC Number: 838-014-1
• SMILES: CC(C)C1=C(C=C(C=C1O)/C=C/C2=CC=CC=C2)O

Properties

• Density: 1.158

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H302-H315-H319-H335
• Precautionary Statements: P261-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	1	H410
Acute hazardous to the aquatic environment	Aquatic Acute	1	H400

Discovory and Applicatios

(E)-2-(1-methylethyl)-5-(2-phenylvinyl)-1,3-benzenediol, also known as trans-resveratrol acetone or simply resveratrol, is a polyphenolic compound found in red wine with potential health benefits. Resveratrol was first isolated from the roots of the plant Veratrum album by Japanese scientist Michio Takaoka in 1940. It gained great attention in the 1990s when it was found in red wine and linked to the "French paradox" - the low incidence of heart disease in the French despite a high saturated fat diet.

Resveratrol has a stilbene skeleton with two aromatic rings connected by an ethylene bridge, hydroxyl groups at positions 3 and 5, an isopropyl group at position 2, and a trans double bond. Resveratrol has two isomers: cis and trans, with the trans form being more stable and more biologically active.

Resveratrol is well known for its potential cardiovascular benefits. It is an antioxidant that reduces oxidative stress and inflammation, which are major contributors to cardiovascular disease. It is able to improve endothelial function and reduce platelet aggregation, further supporting heart health. Studies have shown that resveratrol has anti-cancer properties. It can inhibit cancer cell proliferation, induce apoptosis, and interfere with cancer cell signaling pathways, making it a candidate for cancer prevention and treatment. Resveratrol is gaining popularity in the anti-aging field. It can activate sirtuins, a family of proteins associated with aging and metabolic regulation, which may mimic the effects of caloric restriction and extend lifespan. Studies have shown that resveratrol may provide neuroprotective benefits by reducing neuroinflammation and oxidative damage in the brain, helping to prevent and manage neurodegenerative diseases such as Alzheimer's and Parkinson's.

Resveratrol is widely used as a dietary supplement and is popular for its antioxidant properties and potential health benefits. It is often added to formulas to improve cardiovascular health, support joint function, and promote overall health. Incorporating resveratrol into functional foods and beverages is an emerging trend to enhance the nutritional content of these products using its health benefits.

Resveratrol is incorporated into skin care formulas for its antioxidant and anti-aging properties. It helps protect the skin from environmental stressors, reduces fine lines and wrinkles, and improves skin elasticity. Its ability to mitigate damage caused by UV rays makes resveratrol a great ingredient in sunscreens and after-sun care products to help protect and repair the skin.

Resveratrol can be chemically synthesized or extracted from natural sources such as grapes, berries, and peanuts. The most common natural source is red grape skin, which increases the resveratrol content of red wine.

Resveratrol is generally well tolerated, but high doses may cause gastrointestinal discomfort or interact with certain medications. As with any supplement, it is recommended to consult a physician before use.

Ongoing research aims to explore the full potential of resveratrol in various therapeutic areas and develop improved delivery systems to increase bioavailability. Its role in precision medicine and integrative health practices is also being explored.

References

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2024. Naturally derived bioactive compounds as precision modulators of immune and inflammatory mechanisms in psoriatic conditions. Inflammopharmacology, 32(6).
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2024. The role of aryl hydrocarbon receptor agonists in the treatment of vitiligo. Archives of Dermatological Research, 316(10).
DOI: 10.1007/s00403-024-03405-2