4,4'-Dihydroxystilbene

Base Information

• Chemical Name: 4,4'-Dihydroxystilbene
• CAS No.: 15058-36-3
• Deprecated CAS: 1016644-63-5
• Molecular Formula: C₁₄H₁₂O₂
• Molecular Weight: 212.248
• European Community (EC) Number: 211-530-9
• NSC Number: 4184
• UNII: 921UXX4IZL
• DSSTox Substance ID: DTXSID7022465
• Nikkaji Number: J205.956H,J303.856D
• Wikidata: Q27891518
• Metabolomics Workbench ID: 27959
• ChEMBL ID: CHEMBL196731
• Mol file: 15058-36-3.mol

Synonyms:4,4'-dihydroxy-trans-stilbene;4,4'-dihydroxystilbene;4,4'-stilbenediol

Chemical Property of 4,4'-Dihydroxystilbene

Chemical Property:

• Melting Point: 279-281 °C
• Boiling Point: 386°Cat760mmHg
• PKA: 9.82±0.26(Predicted)
• Flash Point: 188.4°C
• PSA: 0.00000
• Density: 1.252g/cm³
• LogP: 0.00000
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 212.083729621
• Heavy Atom Count: 16
• Complexity: 197

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC(=CC=C1C=CC2=CC=C(C=C2)O)O
• Isomeric SMILES: C1=CC(=CC=C1/C=C/C2=CC=C(C=C2)O)O

Technology Process of 4,4'-Dihydroxystilbene

There total 64 articles about 4,4'-Dihydroxystilbene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(E)-1,2-bis(4-tert-butyldimethylsilyloxyphenyl)ethene → trans-4,4'-dihydroxystilbene (659-22-3,15058-36-3,29884-51-3)

Guidance literature:

With copper(ll) bromide; In acetonitrile; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2006.09.073

Reference yield: 97.0%

1,2-bis(4-methoxyphenyl)ethene (4705-34-4,15638-14-9,34480-01-8,112246-67-0,2510-75-0) → trans-4,4'-dihydroxystilbene (659-22-3,15058-36-3,29884-51-3)

Guidance literature:

With boron tribromide; In dichloromethane; at 20 ℃; for 15h; Cooling with ice;

DOI:10.1093/glycob/cwz034

Reference yield: 93.0%

4-hydroxy-benzaldehyde (123-08-0,65581-83-1) → trans-4,4'-dihydroxystilbene (659-22-3,15058-36-3,29884-51-3)

Guidance literature:

With bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; for 4h; Inert atmosphere; Reflux;

DOI:10.1021/ja906083c

upstream raw materials:

1,2-bis(4-methoxyphenyl)ethene

(E)-1,2-bis(4-ethoxyphenyl)ethene

(E)-4,4'-diaminostilbene

3,5-dimethoxystyrene

Downstream raw materials:

4,4'-ethanediylidene-bis-cyclohexa-2,5-dienone

4,4'-Di(2-cyanoethoxy)-stilben

trans-4,4'-Bis-(α-carboxypropioxy)-stilben

4,4'-ethanediyl-bis-cyclohexanol

Refernces

• 1、 Zhou, Cheng,Chia, Geraldine W. N.,Ho, James C. S.,Seviour, Thomas,Sailov, Talgat,Liedberg, Bo,Kjelleberg, Staffan,Hinks, Jamie,Bazan, Guillermo C.. "Informed Molecular Design of Conjugated Oligoelectrolytes To Increase Cell Affinity and Antimicrobial Activity". . p. 8069 - 8072. Retrieved 2018.
• 2、 Aranda, Carmen,Ullrich, René,Kiebist, Jan,Scheibner, Katrin,Del Río, José C.,Hofrichter, Martin,Martínez, Angel T.,Gutiérrez, Ana. "Selective synthesis of the resveratrol analogue 4,4′-dihydroxy-: Trans -stilbene and stilbenoids modification by fungal peroxygenases". . p. 2394 - 2401. Retrieved 2018.
• 3、 Ochoa, Cristian,Solinski, Amy E.,Nowlan, Marcus,Dekarske, Madeline M.,Wuest, William M.,Kozlowski, Marisa C.. "A Bisphenolic Honokiol Analog Outcompetes Oral Antimicrobial Agent Cetylpyridinium Chloride via a Membrane-Associated Mechanism". . p. 74 - 79. Retrieved 2019/11/20.
• 4、 Yang., Jinfei,Wang, Chengniu,Sun, Yufeng,Man, Xuyan,Li, Jinxia,Sun, Fei. "Ligand-controlled iridium-catalyzed semihydrogenation of alkynes with ethanol: highly stereoselective synthesis of E- and Z-alkenes". supporting information. p. 1903 - 1906. Retrieved 2019/05/02.