Cas no 83088-28-2 (Gigantol)

Gigantol structure
Gigantol structure
Product Name:Gigantol
CAS No:83088-28-2
MF:C16H18O4
MW:274.311725139618
CID:2078708
PubChem ID:10221179
Update Time:2024-10-27

Gigantol Chemical and Physical Properties

Names and Identifiers

    • 1-(3'-hydroxy-5'-methoxyphenyl)-2-(4''-hydroxy-5''-methoxyphenyl)ethane
    • 3,4'-dihydroxy-3',5-d
    • 3',4-dihydroxy-3,5'-dimethoxybibenzyl
    • 3,4'-dihydroxy-5,5'-dimethoxydihydrostilbene
    • 4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol
    • gigantol
    • 4-[2-(3-Hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol (ACI)
    • 3′,4-Dihydroxy-3,5′-dimethoxybibenzyl
    • 3′,4-Dihydroxy-5,5′-dimethoxybibenzyl
    • 4′,5-Dihydroxy-3,3′-dimethoxybibenzyl
    • NS00097428
    • BDBM50346823
    • NCGC00386002-01!4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxyphenol
    • HY-N10549
    • CS-0610782
    • 83088-28-2
    • 4-(3-Hydroxy-5-methoxyphenethyl)-2-methoxyphenol
    • CHEMBL219553
    • DTXSID101287414
    • E88569
    • Phenol, 4-[2-(3-hydroxy-5-methoxyphenyl)ethyl]-2-methoxy-
    • 3a(2),4-Dihydroxy-3,5a(2)-dimethoxybibenzyl
    • Gigantol
    • Inchi： 1S/C16H18O4/c1-19-14-8-12(7-13(17)10-14)4-3-11-5-6-15(18)16(9-11)20-2/h5-10,17-18H,3-4H2,1-2H3
    • InChI Key： BMSPEISBKGSBTR-UHFFFAOYSA-N
    • SMILES： OC1C=C(CCC2C=C(OC)C(O)=CC=2)C=C(OC)C=1

Computed Properties

  • Exact Mass: 274.12050905g/mol
  • Monoisotopic Mass: 274.12050905g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 4
  • Heavy Atom Count: 20
  • Rotatable Bond Count: 5
  • Complexity: 284
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 2.7
  • Topological Polar Surface Area: 58.9?2

Gigantol Pricemore >>

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Gigantol Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  3 h, rt
1.2 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl acetate ;  3 h, 60 psi, 30 °C
Reference
Synthesis, biological evaluation, and docking studies of gigantol analogs as calmodulin inhibitors
Reyes-Ramirez, Adelfo; et al, European Journal of Medicinal Chemistry, 2011, 46(7), 2699-2708

Production Method 2

Reaction Conditions
1.1 24 h, rt
2.1 Reagents: Manganese Catalysts: Dibromo[1,2-di(methoxy-κO)ethane]nickel Solvents: Dimethylacetamide ;  16 h, 35 °C
Reference
Nickel-Catalysed Cross-Electrophile Coupling of Benzyl Bromides and Sulfonium Salts towards the Synthesis of Dihydrostilbenes
del Rio-Rodriguez, Roberto; et al, Chemistry - A European Journal, 2022, 28(54),

Production Method 3

Reaction Conditions
1.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  cooled; 2 h, reflux
2.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  cooled
3.1 Reagents: Triethyl phosphite ;  5 h, 140 °C; 140 °C → 120 °C
3.2 Reagents: Sodium methoxide Solvents: Dimethylformamide ;  120 °C; 30 min, 120 °C; overnight, rt
4.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ,  Ethyl acetate ;  3 h, rt
Reference
Synthesis of gigantol
Wang, Zhan; et al, Jingxi Huagong Zhongjianti, 2012, 42(2), 33-35

Production Method 4

Reaction Conditions
1.1 Reagents: Sodium carbonate ,  Potassium carbonate Solvents: Ethanol ;  2 h, reflux
2.1 Reagents: Potassium carbonate Solvents: Acetone ;  2 h, rt → reflux
2.2 Reagents: Potassium carbonate Solvents: Water
3.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  cooled; 2 h, reflux
4.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  cooled
5.1 Reagents: Triethyl phosphite ;  5 h, 140 °C; 140 °C → 120 °C
5.2 Reagents: Sodium methoxide Solvents: Dimethylformamide ;  120 °C; 30 min, 120 °C; overnight, rt
6.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ,  Ethyl acetate ;  3 h, rt
Reference
Synthesis of gigantol
Wang, Zhan; et al, Jingxi Huagong Zhongjianti, 2012, 42(2), 33-35

Production Method 5

Reaction Conditions
1.1 Catalysts: Silica Solvents: Ethanol ;  4 h, 290 °C
Reference
Catalytic depolymerization of Kraft lignin to high yield alkylated-phenols over CoMo/SBA-15 catalyst in supercritical ethanol
Rana, Masud; et al, RSC Advances, 2023, 13(43), 30022-30039

Production Method 6

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ,  Ethyl acetate ;  3 h, rt
Reference
Synthesis of gigantol
Wang, Zhan; et al, Jingxi Huagong Zhongjianti, 2012, 42(2), 33-35

Production Method 7

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl acetate ;  overnight, rt
Reference
Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues
Moodie, Lindon W. K.; et al, Journal of Natural Products, 2017, 80(7), 2001-2011

Production Method 8

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 14 h, rt
1.2 Solvents: Water ;  rt
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethyl acetate ;  overnight, rt
Reference
Prevention of Marine Biofouling Using the Natural Allelopathic Compound Batatasin-III and Synthetic Analogues
Moodie, Lindon W. K.; et al, Journal of Natural Products, 2017, 80(7), 2001-2011

Production Method 9

Reaction Conditions
1.1 Reagents: Manganese Catalysts: Dibromo[1,2-di(methoxy-κO)ethane]nickel Solvents: Dimethylacetamide ;  16 h, 35 °C
Reference
Nickel-Catalysed Cross-Electrophile Coupling of Benzyl Bromides and Sulfonium Salts towards the Synthesis of Dihydrostilbenes
del Rio-Rodriguez, Roberto; et al, Chemistry - A European Journal, 2022, 28(54),

Production Method 10

Reaction Conditions
1.1 Reagents: Triethyl phosphite ;  5 h, 140 °C; 140 °C → 120 °C
1.2 Reagents: Sodium methoxide Solvents: Dimethylformamide ;  120 °C; 30 min, 120 °C; overnight, rt
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ,  Ethyl acetate ;  3 h, rt
Reference
Synthesis of gigantol
Wang, Zhan; et al, Jingxi Huagong Zhongjianti, 2012, 42(2), 33-35

Production Method 11

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Ethanol ;  2 h, 40 °C → reflux
2.1 Reagents: Triethyl phosphite ;  5 h, 140 °C; 140 °C → 120 °C
2.2 Reagents: Sodium methoxide Solvents: Dimethylformamide ;  120 °C; 30 min, 120 °C; overnight, rt
3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ,  Ethyl acetate ;  3 h, rt
Reference
Synthesis of gigantol
Wang, Zhan; et al, Jingxi Huagong Zhongjianti, 2012, 42(2), 33-35

Production Method 12

Reaction Conditions
1.1 Reagents: Boron tribromide Solvents: Dichloromethane ;  rt; 3 h, rt
2.1 24 h, rt
3.1 Reagents: Manganese Catalysts: Dibromo[1,2-di(methoxy-κO)ethane]nickel Solvents: Dimethylacetamide ;  16 h, 35 °C
Reference
Nickel-Catalysed Cross-Electrophile Coupling of Benzyl Bromides and Sulfonium Salts towards the Synthesis of Dihydrostilbenes
del Rio-Rodriguez, Roberto; et al, Chemistry - A European Journal, 2022, 28(54),

Production Method 13

Reaction Conditions
1.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  cooled
2.1 Reagents: Triethyl phosphite ;  5 h, 140 °C; 140 °C → 120 °C
2.2 Reagents: Sodium methoxide Solvents: Dimethylformamide ;  120 °C; 30 min, 120 °C; overnight, rt
3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ,  Ethyl acetate ;  3 h, rt
Reference
Synthesis of gigantol
Wang, Zhan; et al, Jingxi Huagong Zhongjianti, 2012, 42(2), 33-35

Production Method 14

Reaction Conditions
1.1 Reagents: Potassium carbonate Solvents: Acetone ;  2 h, rt → reflux
1.2 Reagents: Potassium carbonate Solvents: Water
2.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ;  cooled; 2 h, reflux
3.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  cooled
4.1 Reagents: Triethyl phosphite ;  5 h, 140 °C; 140 °C → 120 °C
4.2 Reagents: Sodium methoxide Solvents: Dimethylformamide ;  120 °C; 30 min, 120 °C; overnight, rt
5.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ,  Ethyl acetate ;  3 h, rt
Reference
Synthesis of gigantol
Wang, Zhan; et al, Jingxi Huagong Zhongjianti, 2012, 42(2), 33-35

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Gigantol Preparation Products

Gigantol Related Literature

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