Production Method 1

13633-25-5

87657-77-0

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  40 °C; 1 h, 40 °C; 40 °C → 0 °C
1.2 0 °C; 3 h, 0 °C → rt
2.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 2

2426-87-1

14171-89-2

87657-77-0

Reaction Conditions

1.1 -
2.1 Reagents: Hydrogen Catalysts: Palladium
3.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 3

87657-77-0

Reaction Conditions

1.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  0 °C; 1 h, 0 °C
1.2 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 12 h, rt
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  overnight, rt
3.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0.5 h, rt
3.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1
4.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  40 °C; 1 h, 40 °C; 40 °C → 0 °C
4.2 0 °C; 3 h, 0 °C → rt
5.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 4

2270-20-4

87657-77-0

Reaction Conditions

1.1 Reagents: Thionyl chloride
2.1 -
3.1 -
4.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
5.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 5

18162-48-6

121-33-5

87657-77-0

Reaction Conditions

1.1 Reagents: Imidazole Solvents: Dimethylformamide ;  rt; 10 h, rt
2.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  0 °C; 1 h, 0 °C
2.2 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 12 h, rt
3.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0.5 h, rt
3.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1
4.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  rt
5.1 Reagents: Carbon monoxide ,  Selenium ;  30 atm, 50 - 100 °C
6.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 6

78954-23-1

87657-77-0

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 7

87657-77-0

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
2.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 8

81840-57-5

87657-77-0

Reaction Conditions

1.1 Reagents: Carbon monoxide ,  Selenium ;  30 atm, 50 - 100 °C
2.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 9

13633-25-5

1430215-03-4

87657-77-0

Reaction Conditions

1.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  rt
2.1 Reagents: Carbon monoxide ,  Selenium ;  30 atm, 50 - 100 °C
3.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 10

2911627-91-1

87657-77-0

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0.5 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1
2.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  40 °C; 1 h, 40 °C; 40 °C → 0 °C
2.2 0 °C; 3 h, 0 °C → rt
3.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 11

335594-16-6

87657-77-0

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  10 min, rt
2.1 Reagents: Carbon monoxide ,  Selenium ;  30 atm, 50 - 100 °C
3.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 12

87657-77-0

Reaction Conditions

1.1 Reagents: Phosphorus tribromide Solvents: Dichloromethane ;  0 °C; 0 °C → rt; 2 h, rt
2.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  40 °C; 1 h, 40 °C; 40 °C → 0 °C
2.2 0 °C; 3 h, 0 °C → rt
3.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 13

506-82-1

87657-77-0

Reaction Conditions

1.1 -
2.1 -
3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol
4.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 14

87657-77-0

Reaction Conditions

1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  overnight, rt
2.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0.5 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1
3.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  40 °C; 1 h, 40 °C; 40 °C → 0 °C
3.2 0 °C; 3 h, 0 °C → rt
4.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 15

335594-14-4

87657-77-0

Reaction Conditions

1.1 Reagents: Manganese oxide (Mn3O4) Solvents: Pentane ;  2 h, reflux
2.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  10 min, rt
3.1 Reagents: Carbon monoxide ,  Selenium ;  30 atm, 50 - 100 °C
4.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 16

290820-47-2

27152-04-1

87657-77-0

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  20 min, -78 °C
2.1 Reagents: Manganese oxide (Mn3O4) Solvents: Pentane ;  2 h, reflux
3.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  10 min, rt
4.1 Reagents: Carbon monoxide ,  Selenium ;  30 atm, 50 - 100 °C
5.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 17

67442-07-3

87657-77-0

Reaction Conditions

1.1 rt; 12 h, 100 °C
2.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  0 °C; 1 h, 0 °C
2.2 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 12 h, rt
3.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Methanol ;  overnight, rt
4.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0.5 h, rt
4.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1
5.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  40 °C; 1 h, 40 °C; 40 °C → 0 °C
5.2 0 °C; 3 h, 0 °C → rt
6.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 18

458-36-6

69739-34-0

87657-77-0

Reaction Conditions

1.1 Reagents: 2,6-Lutidine Solvents: Dichloromethane ;  30 min, 0 °C
2.1 Solvents: Tetrahydrofuran ;  20 min, -78 °C
3.1 Reagents: Manganese oxide (Mn3O4) Solvents: Pentane ;  2 h, reflux
4.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  10 min, rt
5.1 Reagents: Carbon monoxide ,  Selenium ;  30 atm, 50 - 100 °C
6.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Production Method 19

79-04-9

87657-77-0

Reaction Conditions

1.1 Reagents: Potassium carbonate Solvents: Water ;  5 °C; 1 h, 5 °C
1.2 Solvents: Dichloromethane ;  5 °C; 1 h, 5 °C; 5 °C → rt; 12 h, rt
2.1 rt; 12 h, 100 °C
3.1 Reagents: Potassium tert-butoxide Solvents: Tetrahydrofuran ;  0 °C; 1 h, 0 °C
3.2 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 12 h, rt
4.1 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ;  0.5 h, rt
4.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 1
5.1 Reagents: Magnesium Catalysts: Iodine Solvents: Tetrahydrofuran ;  rt
6.1 Reagents: Carbon monoxide ,  Selenium ;  30 atm, 50 - 100 °C
7.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt

Reference

Concise and efficient total synthesis of oxyphyllacinol, yakuchione-A and yakuchione-B

Shi, Xiang; et al, Synthetic Communications, 2022, 52(4), 513-520

Oxyphyllacinol Raw materials

• 4-(benzyloxy)-3-methoxybenzaldehyde
• 2-chloroacetyl chloride
• tert-butyl(chloro)dimethylsilane
• 1-Bromo-4-phenylbutane
• 2-Propenal, 3-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxyphenyl]-, (2E)-
• (1E)-1-(4-hydroxy-3-methoxyphenyl)-7-phenylhept-1-en-3-one
• 2-chloro-N-methoxy-N-methyl-acetamide
• Yakuchinone A
• Cadmium, dimethyl-
• Coniferaldehyde
• 6-Phenylhexan-2-one
• Benzenepentanol, α-[(1E)-2-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxyphenyl]ethenyl]-
• 2-Propenamide, 3-(4-hydroxy-3-methoxyphenyl)-N-methoxy-N-methyl-, (2E)-
• Benzenepropanamide, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-N,3-dimethoxy-N-methyl-
• Vanillin
• Magnesium, bromo(4-phenylbutyl)-
• 1-Hepten-3-one, 1-[4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-methoxyphenyl]-7-phenyl-, (1E)-
• t-Butyldimethylsilyl Trifluoromethanesulfonate
• 5-Phenylvaleric acid

Oxyphyllacinol Preparation Products

• Oxyphyllacinol (87657-77-0)

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• 2. Evolution of calcium phosphate precipitation in hanging drop vapor diffusion by in situRaman microspectroscopy
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• 3. Evidence of pre-micellar aggregates in aqueous solution of amphiphilic PDMS–PEO block copolymer?
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  Sowmyalakshmi Venkataraman RSC Adv., 2015,5, 73807-73813

• Solvents and Organic Chemicals Organic Compounds Phenylpropanoids and polyketides Diarylheptanoids Linear diarylheptanoids

Introduction to Oxyphyllacinol (CAS No. 87657-77-0)

Oxyphyllacinol, a naturally occurring compound with the chemical identifier CAS No. 87657-77-0, has garnered significant attention in the field of pharmaceutical research due to its unique biochemical properties and potential therapeutic applications. This compound, which belongs to the flavonoid family, has been extensively studied for its pharmacological effects, particularly in the context of cardiovascular health and anti-inflammatory responses. The structural complexity of Oxyphyllacinol contributes to its multifaceted biological activities, making it a subject of intense interest among researchers.

Recent advancements in chemical biology have highlighted the role of Oxyphyllacinol in modulating cellular signaling pathways associated with oxidative stress and inflammation. Studies have demonstrated that this compound exhibits potent antioxidant properties, which are crucial in mitigating damage caused by reactive oxygen species (ROS). The ability of Oxyphyllacinol to scavenge free radicals and inhibit the production of inflammatory mediators has positioned it as a promising candidate for the development of novel therapeutic agents.

The pharmacokinetic profile of Oxyphyllacinol has also been a focus of research, with investigations into its absorption, distribution, metabolism, and excretion (ADME) characteristics. Preliminary findings suggest that Oxyphyllacinol exhibits good bioavailability and stable metabolic pathways, which are essential for its clinical efficacy. Additionally, its low toxicity profile makes it a favorable candidate for further development into a safe and effective pharmaceutical product.

In vitro studies have revealed that Oxyphyllacinol interacts with various biological targets, including enzymes and receptors involved in metabolic regulation. Its ability to modulate these targets has implications for the treatment of metabolic disorders such as diabetes and hyperlipidemia. Furthermore, research indicates that Oxyphyllacinol may have neuroprotective effects, making it a potential candidate for the management of neurodegenerative diseases like Alzheimer's and Parkinson's.

The synthesis and isolation of Oxyphyllacinol have been optimized through advanced chemical methodologies, ensuring high purity and yield. Techniques such as chromatography and spectroscopy have been employed to characterize the compound's structure and confirm its identity. These advancements in synthetic chemistry have facilitated further research into the compound's biological activities and potential therapeutic applications.

The regulatory landscape for the development of new pharmaceuticals necessitates rigorous testing and validation. Current studies on Oxyphyllacinol are focused on addressing these regulatory requirements through comprehensive preclinical trials. These trials aim to evaluate the compound's safety and efficacy in animal models before human clinical trials can commence. The results from these trials will provide critical insights into the potential of Oxyphyllacinol as a therapeutic agent.

The growing body of evidence supporting the therapeutic potential of Oxyphyllacinol has attracted significant interest from both academic researchers and pharmaceutical companies. Collaborative efforts between these entities are expected to accelerate the development process, bringing this promising compound closer to clinical application. The integration of computational modeling and high-throughput screening techniques is also enhancing our understanding of how Oxyphyllacinol interacts with biological systems.

The future prospects for Oxyphyllacinol are bright, with ongoing research exploring its potential applications in various therapeutic areas. As our understanding of its mechanisms of action continues to evolve, so too will its potential as a therapeutic agent. The combination of traditional pharmacological approaches with cutting-edge biotechnological innovations is poised to unlock new possibilities for this remarkable compound.

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• 55094-79-6(3,5-HEPTANEDIOL, 1,7-BIS(3,4-DIMETHOXYPHENYL)-)
• 39728-80-8(4-(3-Hydroxybutyl)-2-methoxyphenol)
• 919090-22-5(3,5-Heptanediol, 1-(4-hydroxy-3-methoxyphenyl)-7-(4-hydroxyphenyl)-)
• 53254-77-6(3,5-Tetradecanediol,1-(4-hydroxy-3-methoxyphenyl)-, (3R,5S)-)
• 408324-11-8(3,5-HEPTANEDIOL, 1,7-BIS(3,4-DIMETHOXYPHENYL)-, (3R,5R)-)
• 768391-39-5(1,10-DODECANEDIOL, 12-(4-HYDROXY-3-METHOXYPHENYL)-)
• 150335-45-8(4-(3R)-3-hydroxybutyl-2-methoxyphenol)
• 402469-45-8(4-(3-Hydroxy-5-phenylpentyl)-2-methoxyphenol)
• 106085-70-5(Benzenepentanol, a-[2-(3,4-dimethoxyphenyl)ethyl]-3,4-dimethoxy-, (R)-)