Cas no 94608-23-8 (cis-trismethoxy Resveratrol (Solution in Ethanol))

cis-trismethoxy Resveratrol (Solution in Ethanol) structure
94608-23-8 structure
Product Name:cis-trismethoxy Resveratrol (Solution in Ethanol)
CAS No:94608-23-8
MF:C17H18O3
MW:270.323025226593
CID:796955
PubChem ID:9878556
Update Time:2024-10-25

cis-trismethoxy Resveratrol (Solution in Ethanol) Chemical and Physical Properties

Names and Identifiers

    • Benzene,1,3-dimethoxy-5-[(1Z)-2-(4-methoxyphenyl)ethenyl]-
    • (Z)-3,5,4'-TRIMETHOXYSTILBENE
    • cis-trismethoxy Resveratrol
    • 1,3-Dimethoxy-5-[(1Z)-2-(4-methoxyphenyl)ethenyl]benzene (ACI)
    • Benzene, 1,3-dimethoxy-5-[2-(4-methoxyphenyl)ethenyl]-, (Z)- (ZCI)
    • (Z)-1-(4-Methoxyphenyl)-2-(3,5-dimethoxyphenyl)ethene
    • (Z)-3,5,4′-Trimethoxystilbene
    • 3,4′,5-Trimethoxy-cis-stilbene
    • SR-01000946368
    • ,3-dimethoxy-5-[(1Z)-2-(4-methoxyphenyl)ethenyl]-benzene
    • (Z)-3,5,40-Trimethoxystilbene
    • 1,3-dimethoxy-5-[(1Z)-2-(4-methoxyphenyl)ethenyl]benzene
    • 1,3-dimethoxy-5-[(1z)-2-(4-methoxyphenyl)ethenyl]-benzene, AldrichCPR
    • cis-Stilbene Derivative, 5a
    • HY-121989
    • A845021
    • AKOS025401671
    • cis-Trismethoxyresveratrol
    • SCHEMBL1006207
    • HMS3648G16
    • BDBM23940
    • SR-01000946368-1
    • CS-0083811
    • cis-trismethoxy Resveratrol (Solution in Ethanol)
    • CHEMBL311636
    • AC-24237
    • (Z)-3,4',5-trimethoxystilbene
    • (z)-1,3-dimethoxy-5-(4-methoxystyryl)benzene
    • 94608-23-8
    • 1,3-dimethoxy-5-[(Z)-2-(4-methoxyphenyl)ethenyl]benzene
    • DTXSID501306933
    • GDHNBPHYVRHYCC-PLNGDYQASA-N
    • 8Z-3,4',5-trimethoxystilbene
    • CIS-TRIMETHOXY STILBENE
    • (Z)-3,5,4a(2)-Trimethoxystilbene
    • Inchi: 1S/C17H18O3/c1-18-15-8-6-13(7-9-15)4-5-14-10-16(19-2)12-17(11-14)20-3/h4-12H,1-3H3/b5-4-
    • InChI Key: GDHNBPHYVRHYCC-PLNGDYQASA-N
    • SMILES: C(/C1C=C(OC)C=C(OC)C=1)=C/C1C=CC(OC)=CC=1

Computed Properties

  • Exact Mass: 270.125594432g/mol
  • Monoisotopic Mass: 270.125594432g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 5
  • Complexity: 283
  • 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
  • XLogP3: 4.1
  • Topological Polar Surface Area: 27.7?2

Experimental Properties

  • Density: 1.1±0.1 g/cm3
  • Melting Point: 57 °C
  • Boiling Point: 423.8±35.0 °C at 760 mmHg
  • Flash Point: 144.4±23.2 °C
  • Refractive Index: 1.6
  • PSA: 27.69000
  • LogP: 3.88280
  • Vapor Pressure: 0.0±1.0 mmHg at 25°C

cis-trismethoxy Resveratrol (Solution in Ethanol) Security Information

cis-trismethoxy Resveratrol (Solution in Ethanol) Pricemore >>

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cis-trismethoxy Resveratrol (Solution in Ethanol) Production Method

Production Method 1

Reaction Conditions
1.1 Solvents: Ethanol ;  1 h
Reference
Method for the synthesis of (Z)-3,5,4'-trimethoxystilbene, a trimethyl derivative of resveratrol, the resulting compound, and uses of said compound, in particular as a medicine, and particularly as an anticancer drug
, World Intellectual Property Organization, , ,

Production Method 2

Reaction Conditions
1.1 Reagents: 1,10-Phenanthroline ,  Quinoline ,  Copper ;  50 min, heated
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 6, cooled
Reference
Method for preparing diphenylethylene from 2,3-diphenyl acrylic acid
, China, , ,

Production Method 3

Reaction Conditions
1.1 Reagents: Chlorotrimethylsilane ,  Hydrogen ,  Magnesium Catalysts: (OC-6-31)-Aqua[1-[2,6-bis(1-methylethyl)phenyl]-3-[1-[[2,6-bis(1-methylethyl)phe… Solvents: Tetrahydrofuran ;  24 h, 90 - 100 °C
Reference
Chromium-catalyzed stereodivergent E- and Z-selective alkyne hydrogenation controlled by cyclic (alkyl)(amino)carbene ligands
Ling, Liang ; Hu, Chenyang ; Long, Linhong; Zhang, Xue ; Zhao, Lixing ; et al, Nature Communications, 2023, 14(1),

Production Method 4

Reaction Conditions
1.1 Reagents: Quinoline ,  Sodium hydroxide Catalysts: Copper ;  0.25 h, 200 °C
Reference
Synthesis of resveratrol
Hou, Bing-bo; Feng, Jiang-jiang; Yang, Sheng-wei; Ao, Gui-zhen, Huaxue Shiji, 2011, 33(12), 1141-1143

Production Method 5

Reaction Conditions
1.1 Reagents: Quinoline Catalysts: Copper ;  3 h, 220 °C
Reference
Efficient synthesis of natural polyphenolic stilbenes: resveratrol, piceatannol and oxyresveratrol
Sun, Hong-Yi; Xiao, Chun-Fen; Cai, Yu-Chen; Chen, Yu; Wei, Wen; et al, Chemical & Pharmaceutical Bulletin, 2010, 58(11), 1492-1496

Production Method 6

Reaction Conditions
1.1 Reagents: Quinoline ,  Copper Catalysts: 1,10-Phenanthroline ;  6 min
1.2 Reagents: Hydrochloric acid Solvents: Water ;  cooled
Reference
Microwave-assisted and ligand-accelerated decarboxylation of 2,3-diaryl acrylic acids
Liu, Xianke; Wu, Wei; Lv, Zeliang; Zou, Yong, Huaxue Tongbao, 2012, 75(6), 526-531

Production Method 7

Reaction Conditions
1.1 Reagents: Quinoline ,  Copper ;  3 h, 200 °C
Reference
Hydroxyl Substitutional Effect on Selective Synthesis of cis, trans Stilbenes and 3-Arylcoumarins Through Perkin Condensation
Xiao, Chun-Fen; Zou, Yong; Du, Jian-Li; Sun, Hong-Yi; Liu, Xian-Ke, Synthetic Communications, 2012, 42(9), 1243-1258

Production Method 8

Reaction Conditions
1.1 Reagents: Diisobutylaluminum hydride Solvents: Diethyl ether ;  0 °C; 0 °C → rt; 16 h, rt
1.2 Reagents: Tetrabutylammonium fluoride Catalysts: Bis(dibenzylideneacetone)palladium Solvents: Tetrahydrofuran
Reference
Diversity-oriented synthesis of disubstituted alkenes using masked silanols
Sore, Hannah F.; Blackwell, David T.; MacDonald, Simon J. F.; Spring, David R., Organic Letters, 2010, 12(12), 2806-2809

Production Method 9

Reaction Conditions
1.1 Solvents: Ethanol ;  1 h, rt
Reference
Anti-mitotic properties of resveratrol analog (Z)-3,5,4'-trimethoxystilbene
Chabert, Philippe; Fougerousse, Andre; Brouillard, Raymond, BioFactors, 2006, 27(1-4), 37-46

Production Method 10

Reaction Conditions
1.1 Reagents: Lithium hydroxide Solvents: Isopropanol ;  60 °C
Reference
E-selective isomerization of stilbenes and stilbenoids through reversible hydroboration
Gray, Erin E.; Rabenold, Lake E.; Goess, Brian C., Tetrahedron Letters, 2011, 52(46), 6177-6179

Production Method 11

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetone ;  5 h, reflux
Reference
Synthesis of radiolabeled stilbene derivatives as new potential PET probes for aryl hydrocarbon receptor in cancers
Gao, Mingzhang; Wang, Min; Miller, Kathy D.; Sledge, George W.; Hutchins, Gary D.; et al, Bioorganic & Medicinal Chemistry Letters, 2006, 16(22), 5767-5772

Production Method 12

Reaction Conditions
1.1 Catalysts: Chromium copper oxide (Cr2CuO4) Solvents: Pyridine ;  rt → 240 °C; 1 - 2 h, 230 - 240 °C; 240 °C → rt
Reference
Improved method for synthesizing resveratrol
, China, , ,

Production Method 13

Reaction Conditions
1.1 Reagents: Lithium tert-butoxide ,  Bis(neopentyl glycolato)diboron Catalysts: (2-Thiophenecarboxylato-κO2,κS1)copper ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Dimethylformamide ,  Water ;  24 h, 60 °C
Reference
Copper-catalysed, diboron-mediated cis-dideuterated semihydrogenation of alkynes with heavy water
Han, Xiaowei; Hu, Jiefeng; Chen, Cheng; Yuan, Yu; Shi, Zhuangzhi, Chemical Communications (Cambridge, 2019, 55(48), 6922-6925

Production Method 14

Reaction Conditions
1.1 Reagents: Deuterium ,  [1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene]hydroxy… Catalysts: 1,1-Bis(diphenylphosphino)ferrocene ,  Nickel iodide (NiI2) Solvents: Tetrahydrofuran ;  100 bar, 60 °C
Reference
A simple nickel catalyst enables broad E-selective alkyne semihydrogenation
Thiel, Niklas O.; Kaewmee, Benyapa; Ngoc, Trung Tran; Teichert, Johannes F., ChemRxiv, 2019, 1, 1-7

Production Method 15

Reaction Conditions
1.1 Reagents: Quinoline ,  Potassium hydroxide ,  Copper bromide (CuBr) ;  0.5 h, 190 °C
Reference
Method for preparation of (E)-Resveratrol
, China, , ,

Production Method 16

Reaction Conditions
1.1 Reagents: Tributylamine Catalysts: Copper oxide (Cu2O) Solvents: N-Methyl-2-pyrrolidone ;  90 min, 200 °C
Reference
Stereospecific synthesis of cis-stilbenes from benzaldehydes and phenylacetic acids via sequential Perkin condensation and decarboxylation
Thompson, Clayton M.; Orellana, Matthew D.; Lloyd, Shannon E.; Wu, Weiming, Tetrahedron Letters, 2016, 57(43), 4866-4868

Production Method 17

Reaction Conditions
1.1 Reagents: Sodium hydroxide Catalysts: Palladium diacetate ,  2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl Solvents: Tetrahydrofuran ;  6 h, 23 °C
Reference
(Z)-(2-Bromovinyl)-MIDA boronate: a readily accessible and highly versatile building block for small molecule synthesis
Woerly, Eric M.; Struble, Justin R.; Palyam, Nagarjuna; O'Hara, Sean P.; Burke, Martin D., Tetrahedron, 2011, 67(24), 4333-4343

Production Method 18

Reaction Conditions
1.1 Reagents: Copper Solvents: Quinoline ;  4 h, 220 °C
Reference
An efficient synthesis of resveratrol and a hydroxyl derivative via the perkin reaction: cis to trans isomerization in a demethylation process
Li, Guoxing; Zou, Yong; Zhang, Xuejing, Journal of Chemical Research, 2007, (11), 657-659

Production Method 19

Reaction Conditions
1.1 Reagents: Butyllithium Solvents: Tetrahydrofuran ,  Hexane ;  -78 °C; 30 min, -78 °C; 1 h, rt; rt → -78 °C
1.2 Solvents: Tetrahydrofuran ;  1 h, -78 °C; 18 h, rt
Reference
2-Amino and 2'-Aminocombretastatin Derivatives as Potent Antimitotic Agents
Chang, Jang-Yang; Yang, Ming-Fang; Chang, Chi-Yen; Chen, Chi-Ming; Kuo, Ching-Chuan; et al, Journal of Medicinal Chemistry, 2006, 49(21), 6412-6415

Production Method 20

Reaction Conditions
1.1 Reagents: Hydrogen Solvents: Ethanol ;  3.3 min, 2 bar, 60 °C
Reference
Preparation of substituted electron rich diphenylacetylenes and stilbene derivatives
, World Intellectual Property Organization, , ,

cis-trismethoxy Resveratrol (Solution in Ethanol) Raw materials

cis-trismethoxy Resveratrol (Solution in Ethanol) Preparation Products

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