- 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, , ,
Cas no 94608-23-8 (cis-trismethoxy Resveratrol (Solution in Ethanol))
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
- Signal Word:warning
- Hazard Statement: H303+H313+H333
- Warning Statement: P264+P280+P305+P351+P338+P337+P313
- Hazard Category Code: 41
- Safety Instruction: 26-39
-
Hazardous Material Identification:
- Storage Condition:storage at -4℃ (1-2weeks), longer storage period at -20℃ (1-2years)
cis-trismethoxy Resveratrol (Solution in Ethanol) Pricemore >>
| Related Categories | No. | Product Name | Cas No. | Purity | Specification | Price | update time | Inquiry |
|---|---|---|---|---|---|---|---|---|
| SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd. | R913176-50mg |
cis-trismethoxy Resveratrol (cis-Trimethoxy Stilbene) |
94608-23-8 | 98% | 50mg |
¥2,045.70 | 2022-08-31 | |
| WU HAN AN JIE KAI Biomedical Technology Co., Ltd. | ajci8946-50mg |
cis-trismethoxy Resveratrol |
94608-23-8 | 98% | 50mg |
¥453.00 | 2023-09-09 | |
| WU HAN AN JIE KAI Biomedical Technology Co., Ltd. | ajci8946-100mg |
cis-trismethoxy Resveratrol |
94608-23-8 | 98% | 100mg |
¥869.00 | 2023-09-09 | |
| WU HAN AN JIE KAI Biomedical Technology Co., Ltd. | ajci8946-500mg |
cis-trismethoxy Resveratrol |
94608-23-8 | 98% | 500mg |
¥3368.00 | 2023-09-09 | |
| TRC | R150133-5mg |
cis-trismethoxy Resveratrol (Solution in Ethanol) |
94608-23-8 | 5mg |
$ 63.00 | 2023-09-06 | ||
| TRC | R150133-10mg |
cis-trismethoxy Resveratrol (Solution in Ethanol) |
94608-23-8 | 10mg |
$ 75.00 | 2023-09-06 | ||
| TRC | R150133-50mg |
cis-trismethoxy Resveratrol (Solution in Ethanol) |
94608-23-8 | 50mg |
$ 270.00 | 2023-09-06 | ||
| TRC | R150133-100mg |
cis-trismethoxy Resveratrol (Solution in Ethanol) |
94608-23-8 | 100mg |
$356.00 | 2023-05-17 | ||
| SHENG KE LU SI SHENG WU JI SHU | sc-205255-10 mg |
cis-trismethoxy Resveratrol, |
94608-23-8 | ≥98% | 10mg |
¥181.00 | 2023-07-10 | |
| SHENG KE LU SI SHENG WU JI SHU | sc-205255A-50 mg |
cis-trismethoxy Resveratrol, |
94608-23-8 | ≥98% | 50mg |
¥812.00 | 2023-07-10 |
cis-trismethoxy Resveratrol (Solution in Ethanol) Production Method
Production Method 1
Reaction Conditions
1.1 Solvents: Ethanol ; 1 h
Reference
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
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 ligandsLing, 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 resveratrolHou, 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 oxyresveratrolSun, 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
1.2 Reagents: Hydrochloric acid Solvents: Water ; cooled
Reference
- Microwave-assisted and ligand-accelerated decarboxylation of 2,3-diaryl acrylic acidsLiu, 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 CondensationXiao, 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
1.2 Reagents: Tetrabutylammonium fluoride Catalysts: Bis(dibenzylideneacetone)palladium Solvents: Tetrahydrofuran
Reference
- Diversity-oriented synthesis of disubstituted alkenes using masked silanolsSore, 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'-trimethoxystilbeneChabert, 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 hydroborationGray, 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 cancersGao, 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 waterHan, 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 semihydrogenationThiel, 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 decarboxylationThompson, 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 synthesisWoerly, 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 processLi, 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
1.2 Solvents: Tetrahydrofuran ; 1 h, -78 °C; 18 h, rt
Reference
- 2-Amino and 2'-Aminocombretastatin Derivatives as Potent Antimitotic AgentsChang, 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
- 1-Bromo-3,5-dimethoxybenzene
- Benzeneacetic acid, α-[(3,5-dimethoxyphenyl)methylene]-4-methoxy-, (αE)-
- (αE)-3,5-Dimethoxy-α-[(4-methoxyphenyl)methylene]benzeneacetic acid
- 1-[[2-(3,5-Dimethoxyphenyl)ethynyl]dimethylsilyl]-2,3,4,5,6-pentafluorobenzene
- (Z)-Pterostilbene
- (4-Methoxybenzyl)triphenylphosphonium bromide
- 4-Iodoanisole
- trans-Trimethoxyresveratrol
- Benzene, 1,3-dimethoxy-5-[(4-methoxyphenyl)ethynyl]-
- 3,5-Dimethoxybenzaldehyde
cis-trismethoxy Resveratrol (Solution in Ethanol) Preparation Products
cis-trismethoxy Resveratrol (Solution in Ethanol) Related Literature
-
Xiaotong Feng,Lei Bian,Jie Ma,Lei Zhou,Xiayan Wang,Guangsheng Guo,Qiaosheng Pu Chem. Commun., 2019,55, 3963-3966
-
Ana G. Neo,Ana Bornadiego,Jesús Díaz,Stefano Marcaccini,Carlos F. Marcos Org. Biomol. Chem., 2013,11, 6546-6555
-
Eléonore Resongles,Corinne Casiot,Fran?oise Elbaz-Poulichet,Rémi Freydier,Odile Bruneel,Christine Piot,Sophie Delpoux,Aurélie Volant,Angélique Desoeuvre Environ. Sci.: Processes Impacts, 2013,15, 1536-1544
-
Ross Harder,David C. Dunand,Ian McNulty Nanoscale, 2017,9, 5686-5693
94608-23-8 (cis-trismethoxy Resveratrol (Solution in Ethanol)) Related Products
- 104-46-1(Anethole)
- 25679-28-1(Cis-Anethole)
- 21956-56-9(trans-3,5-Dimethoxystilbene)
- 117048-59-6(Combretastatin A4)
- 537-42-8(Pterostilbene)
- 1142-15-0(4-Methoxystilbene)
- 4180-23-8(1-Methoxy-4-(1E)-1-propen-1-ylbenzene)
- 15638-14-9(4,4'-Dimethoxystilbene)
- 18259-15-9(Phenol,4-[2-(3,5-dimethoxyphenyl)ethenyl]-)
- 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
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