Cas no 659-22-3 (4,4-Dihydroxystilbene)

4,4-Dihydroxystilbene is a stilbene derivative characterized by the presence of hydroxyl groups at the para positions of its phenyl rings. This compound is of interest in organic synthesis and materials science due to its conjugated double bond system, which contributes to its potential applications in photochemistry and as a building block for advanced polymers. Its symmetrical structure and phenolic functional groups make it a versatile intermediate for the preparation of antioxidants, UV absorbers, and fluorescent probes. The compound exhibits moderate solubility in polar organic solvents, facilitating its use in various chemical modifications. Its stability and reactivity under controlled conditions further enhance its utility in research and industrial applications.
4,4-Dihydroxystilbene structure
4,4-Dihydroxystilbene structure
Product Name:4,4-Dihydroxystilbene
CAS No:659-22-3
MF:C14H12O2
MW:212.243884086609
MDL:MFCD00016487
CID:1697403
PubChem ID:92830
Update Time:2025-05-26

4,4-Dihydroxystilbene Chemical and Physical Properties

Names and Identifiers

    • stilbene-4,4'-diol
    • 4,4'-Dihydroxystilbene
    • 4,4'-Dioxystilbene
    • NSC 4184
    • p,p'-Dihydroxystilbene
    • Phenol, 4,4'-(1,2-ethenediyl)bis-
    • 4,4'-ethene-1,2-diyldiphenol
    • 4,4'-(E)-ethene-1,2-diyldiphenol
    • (E)-4-<2-(4-hydroxyphenyl)ethenyl>phenol
    • 4,4'-(1,2-Ethenediyl)bisphenol
    • 4,4'-Dihydroxy-trans-stilbene
    • 4,4'-Stilbenediol
    • 4-[(E)-2-(4-hydroxyphenyl)ethenyl]phenol
    • 4-hydroxyl-4'-hydroxyl-trans-stilbene
    • DIHYDROXYSTILBENE,4,4'-(P)
    • E-4,4'-(1,2-ethenediyl)bisphenol
    • trans-4,4'-dihydroxystilbene
    • trans-Stilbene-4,4'-diol
    • cis-stilbene-4,4'-diol
    • P7HHM32U5K
    • 4,4'-(Z)-ethene-1,2-diyldiphenol
    • 4,4'-[(1Z)-ethene-1,2-diyl]diphenol
    • 4,4'-Stilbenediol, (Z)-
    • 4,4'-(Z)ethene-1,2-diyldiphenol
    • 4,4'-[(Z)-Ethene-1,2-diyl]bisphenol
    • 4-[2-(4-hydroxyphenyl)ethenyl]phenol
    • SCHEMBL145659
    • XLAIWHIOIFKLEO-UHFFFAOYSA-N
    • FT-0772398
    • Oprea1_012705
    • (E/Z)-4-[2-(4-hydroxyphenyl)ethenyl]phenol
    • AKOS028108539
    • DTXSID70859527
    • Q27116022
    • 4,4'-(Ethene-1,2-diyl)diphenol
    • CHEMBL196731
    • NSC4184
    • (E)-4,4'-Dihydroxystilbene
    • XLAIWHIOIFKLEO-OWOJBTEDSA-N
    • LMPK13090018
    • 4,4/'-(Z)-ETHENE-1,2-DIYLDIPHENOL
    • Q27891518
    • EINECS 211-530-9
    • 6DRS5V9W5C
    • 4,4'-Stilbenediol, (E)-
    • 4-[(1E)-2-(4-hydroxyphenyl)ethenyl]phenol
    • 4,4'-dihydroxy stibene
    • Phenol, 4,4'-(1,2-ethenediyl)bis-, (E)-
    • CHEBI:36012
    • trans-4,4'-Stilbenediol
    • UNII-921UXX4IZL
    • CHEBI:34368
    • Phenol, 4,4'-(1E)-1,2-ethenediylbis-
    • BDBM50410524
    • (e)-4,4'-(ethene-1,2-diyl)diphenol
    • 659-22-3
    • NS00035932
    • DTXSID7022465
    • 921UXX4IZL
    • UNII-6DRS5V9W5C
    • 4,4'-[(1E)-ethene-1,2-diyl]diphenol
    • NSC-4184
    • Phenol,4'-(1,2-ethenediyl)bis-
    • 15058-36-3
    • (E)-4,4'-stilbenediol
    • AKOS000278359
    • BIDD:ER0188
    • 4,4-Dihydroxystilbene
    • MDL: MFCD00016487
    • Inchi: 1S/C14H12O2/c15-13-7-3-11(4-8-13)1-2-12-5-9-14(16)10-6-12/h1-10,15-16H/b2-1+
    • InChI Key: XLAIWHIOIFKLEO-OWOJBTEDSA-N
    • SMILES: OC1C=CC(=CC=1)/C=C/C1C=CC(=CC=1)O

Computed Properties

  • Exact Mass: 212.08400
  • Monoisotopic Mass: 212.083729621g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 16
  • Rotatable Bond Count: 2
  • Complexity: 197
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 1
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: 5
  • XLogP3: 3.5
  • Topological Polar Surface Area: 40.5

Experimental Properties

  • Density: 1.3±0.1 g/cm3
  • Melting Point: Not available
  • Boiling Point: 386.0±11.0 °C at 760 mmHg
  • Flash Point: 188.3±13.9 °C
  • Refractive Index: 1.726
  • PSA: 40.46000
  • LogP: 3.26820
  • Vapor Pressure: 0.0±0.9 mmHg at 25°C

4,4-Dihydroxystilbene Pricemore >>

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Additional information on 4,4-Dihydroxystilbene

4,4-Dihydroxystilbene (CAS No. 659-22-3): A Comprehensive Overview

4,4-Dihydroxystilbene (CAS No. 659-22-3) is a naturally occurring compound that has garnered significant attention in the fields of chemistry, biology, and pharmacology due to its diverse biological activities and potential therapeutic applications. This compound, also known as resveratrol, is primarily found in the skin of red grapes, peanuts, and certain berries. Its unique chemical structure and biological properties have made it a subject of extensive research over the past few decades.

The chemical structure of 4,4-Dihydroxystilbene consists of two hydroxyl groups attached to a stilbene backbone. This structure confers the compound with antioxidant, anti-inflammatory, and anti-cancer properties. Recent studies have further elucidated the mechanisms by which 4,4-Dihydroxystilbene exerts its biological effects, providing valuable insights into its potential therapeutic applications.

In the realm of antioxidant activity, 4,4-Dihydroxystilbene has been shown to scavenge free radicals and protect cells from oxidative stress. A study published in the Journal of Agricultural and Food Chemistry demonstrated that 4,4-Dihydroxystilbene effectively inhibited lipid peroxidation in human cell lines, thereby reducing the risk of cellular damage and inflammation. This property makes it a promising candidate for the prevention and treatment of various oxidative stress-related diseases.

Beyond its antioxidant capabilities, 4,4-Dihydroxystilbene has also been investigated for its anti-inflammatory properties. Research conducted at the University of California, Los Angeles (UCLA) revealed that 4,4-Dihydroxystilbene can modulate the expression of pro-inflammatory cytokines such as TNF-α and IL-6. By downregulating these cytokines, 4,4-Dihydroxystilbene can help alleviate chronic inflammation associated with conditions like arthritis and cardiovascular disease.

The anti-cancer potential of 4,4-Dihydroxystilbene has been another area of intense research. Studies have shown that this compound can induce apoptosis (programmed cell death) in various cancer cell lines while sparing normal cells. A notable study published in the Cancer Research journal reported that 4,4-Dihydroxystilbene inhibited the growth of human breast cancer cells by disrupting cell cycle progression and inducing DNA damage. These findings suggest that 4,4-Dihydroxystilbene could be a valuable adjunctive therapy in cancer treatment regimens.

In addition to its direct biological effects, 4,4-Dihydroxystilbene has been explored for its neuroprotective properties. Research at the University of Cambridge found that this compound can protect neurons from oxidative stress and neuroinflammation, which are key factors in neurodegenerative diseases such as Alzheimer's and Parkinson's disease. The ability of 4,4-Dihydroxystilbene to cross the blood-brain barrier further enhances its potential as a neuroprotective agent.

The cardiovascular benefits of 4,4-Dihydroxystilbene have also been well-documented. Studies have shown that this compound can improve endothelial function, reduce blood pressure, and lower cholesterol levels. A clinical trial conducted at Harvard Medical School demonstrated that supplementation with 4,4-Dihydroxystilbene-rich grape extract significantly reduced markers of cardiovascular risk in patients with metabolic syndrome.

In conclusion, 4,4-Dihydroxystilbene (CAS No. 659-22-3), also known as resveratrol, is a multifaceted compound with a wide range of biological activities. Its antioxidant, anti-inflammatory, anti-cancer, neuroprotective, and cardiovascular benefits make it a promising candidate for various therapeutic applications. Ongoing research continues to uncover new mechanisms and potential uses for this remarkable compound, solidifying its position as a valuable asset in the fields of chemistry and pharmacology.

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