Production Method 1

32811-40-8

81446-29-9

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Laccase Solvents: Ethanol ,  Water ;  pH 5, rt; 1 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

An enantiocomplementary dirigent protein for the enantioselective laccase-catalyzed oxidative coupling of phenols

Pickel, Benjamin; et al, Angewandte Chemie, 2010, 49(1), 202-204

Production Method 2

38759-91-0

81446-29-9

95404-51-6

Reaction Conditions

1.1 Reagents: Glucose ,  Sucrose ,  Potassium chloride ,  Sulfuric acid magnesium salt (1:1) ,  Ferrous sulfate ,  Dipotassium phosphate Solvents: Dimethyl sulfoxide ,  Water ;  72 h, 25 °C

Reference

Enantioselective accumulation of (-)-pinoresinol through O-demethylation of (±)-eudesmin by Aspergillus niger

Kasahara, Hiroyuki; et al, Phytochemistry, 1997, 44(8), 1479-1482

Production Method 3

487-36-5

81446-29-9

95404-51-6

Reaction Conditions

1.1 24 h, rt
2.1 Reagents: Glucose ,  Sucrose ,  Potassium chloride ,  Sulfuric acid magnesium salt (1:1) ,  Ferrous sulfate ,  Dipotassium phosphate Solvents: Dimethyl sulfoxide ,  Water ;  72 h, 25 °C

Reference

Enantioselective accumulation of (-)-pinoresinol through O-demethylation of (±)-eudesmin by Aspergillus niger

Kasahara, Hiroyuki; et al, Phytochemistry, 1997, 44(8), 1479-1482

Production Method 4

458-35-5

81446-29-9

27003-73-2

83327-19-9

29388-59-8

487-36-5

Reaction Conditions

1.1 Reagents: NADPH ,  Hydrogen peroxide Solvents: Water ;  1 h, pH 7, 30 °C

Reference

Enantioselective lignan synthesis by cell-free extracts of Forsythia koreana

Umezawa, Toshiaki; et al, Bioscience, 1994, 58(2), 230-4

Production Method 5

526-06-7

81446-29-9

Reaction Conditions

1.1 Reagents: Glucose ,  Sucrose ,  Potassium chloride ,  Sulfuric acid magnesium salt (1:1) ,  Ferrous sulfate ,  Dipotassium phosphate Solvents: Dimethyl sulfoxide ,  Water ;  72 h, 25 °C

Reference

Enantioselective accumulation of (-)-pinoresinol through O-demethylation of (±)-eudesmin by Aspergillus niger

Kasahara, Hiroyuki; et al, Phytochemistry, 1997, 44(8), 1479-1482

Production Method 6

28028-62-8

81446-29-9

Reaction Conditions

1.1 Reagents: Diisobutylaluminum hydride Solvents: Toluene ;  40 min, 0 °C; 1 h, 0 °C
2.1 Reagents: Oxygen Catalysts: Laccase Solvents: Ethanol ,  Water ;  pH 5, rt; 1 h, rt
2.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

An enantiocomplementary dirigent protein for the enantioselective laccase-catalyzed oxidative coupling of phenols

Pickel, Benjamin; et al, Angewandte Chemie, 2010, 49(1), 202-204

Production Method 7

537-98-4

81446-29-9

Reaction Conditions

1.1 Reagents: Acetyl chloride Solvents: Ethanol ;  0 °C; 2 d, rt
2.1 Reagents: Diisobutylaluminum hydride Solvents: Toluene ;  40 min, 0 °C; 1 h, 0 °C
3.1 Reagents: Oxygen Catalysts: Laccase Solvents: Ethanol ,  Water ;  pH 5, rt; 1 h, rt
3.2 Reagents: Hydrochloric acid Solvents: Water ;  acidified

Reference

An enantiocomplementary dirigent protein for the enantioselective laccase-catalyzed oxidative coupling of phenols

Pickel, Benjamin; et al, Angewandte Chemie, 2010, 49(1), 202-204

Production Method 8

23397-46-8

81446-29-9

95404-51-6

Reaction Conditions

1.1 Reagents: Glucose ,  Sucrose ,  Potassium chloride ,  Sulfuric acid magnesium salt (1:1) ,  Ferrous sulfate ,  Dipotassium phosphate Solvents: Dimethyl sulfoxide ,  Water ;  72 h, 25 °C

Reference

Enantioselective accumulation of (-)-pinoresinol through O-demethylation of (±)-eudesmin by Aspergillus niger

Kasahara, Hiroyuki; et al, Phytochemistry, 1997, 44(8), 1479-1482

Production Method 9

32811-40-8

81446-29-9

487-36-5

Reaction Conditions

1.1 Reagents: Oxygen ;  2 h, pH 4.5, 45 °C

Reference

Laccase catalyses phytophenol furanocyclic dimerization: Substrate specificity and diastereoselective process

Li, Xican ; et al, Journal of Molecular Structure, 2023, 1274,

Production Method 10

81446-29-9

95404-51-6

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Diethyl ether ;  3 h, rt
2.1 Reagents: Glucose ,  Sucrose ,  Potassium chloride ,  Sulfuric acid magnesium salt (1:1) ,  Ferrous sulfate ,  Dipotassium phosphate Solvents: Dimethyl sulfoxide ,  Water ;  72 h, 25 °C

Reference

Enantioselective accumulation of (-)-pinoresinol through O-demethylation of (±)-eudesmin by Aspergillus niger

Kasahara, Hiroyuki; et al, Phytochemistry, 1997, 44(8), 1479-1482

(-)-pinoresinol Raw materials

• (E)-Ferulic acid
• (+)-de-4'-O-methyleudesmin
• (E)-Coniferol
• Coniferyl alcohol
• Eudesmin
• Pinoresinol
• (-)-Eudesmin
• 2-Propenoic acid, 3-(4-hydroxy-3-methoxyphenyl)-, ethyl ester, (E)-

(-)-pinoresinol Preparation Products

• Lariciresinol (27003-73-2)
• (-)-Lariciresinol (83327-19-9)
• Secoisolariciresinol (29388-59-8)
• Pinoresinol (487-36-5)
• (+)-de-4'-O-methyleudesmin (95404-51-6)
• (-)-pinoresinol (81446-29-9)

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• Solvents and Organic Chemicals Organic Compounds Lignans, neolignans and related compounds Furanoid lignans Furanoid lignans
• Solvents and Organic Chemicals Organic Compounds Lignans, neolignans and related compounds Furanoid lignans

Recent Advances in the Study of (-)-Pinoresinol (CAS: 81446-29-9): A Comprehensive Research Brief

(-)-Pinoresinol, a lignan compound with the CAS number 81446-29-9, has garnered significant attention in the field of chemical biology and pharmaceutical research due to its diverse biological activities. Recent studies have explored its potential applications in anti-inflammatory, antioxidant, and anticancer therapies. This research brief synthesizes the latest findings on (-)-pinoresinol, focusing on its molecular mechanisms, therapeutic potential, and recent advancements in extraction and synthesis methodologies.

One of the most notable breakthroughs in (-)-pinoresinol research is its role in modulating inflammatory pathways. A 2023 study published in the *Journal of Natural Products* demonstrated that (-)-pinoresinol significantly inhibits the NF-κB signaling pathway, reducing the production of pro-inflammatory cytokines such as TNF-α and IL-6. This finding suggests its potential as a lead compound for developing novel anti-inflammatory drugs. Additionally, its antioxidant properties have been linked to the scavenging of reactive oxygen species (ROS), which are implicated in various chronic diseases.

In the realm of cancer research, (-)-pinoresinol has shown promise as an adjuvant therapy. A recent in vitro study revealed its ability to induce apoptosis in human breast cancer cells (MCF-7) by upregulating caspase-3 activity and downregulating Bcl-2 expression. These results, published in *Bioorganic & Medicinal Chemistry Letters*, highlight the compound's potential to enhance the efficacy of conventional chemotherapeutic agents while minimizing side effects.

Advances in the extraction and synthesis of (-)-pinoresinol have also been reported. A 2024 study in *Green Chemistry* introduced a sustainable enzymatic method for the stereoselective synthesis of (-)-pinoresinol, achieving a yield of 85% with minimal environmental impact. This method addresses the challenges associated with traditional chemical synthesis, such as low selectivity and high energy consumption, paving the way for scalable production.

Despite these promising developments, challenges remain in the clinical translation of (-)-pinoresinol. Pharmacokinetic studies indicate low oral bioavailability, necessitating the development of novel drug delivery systems. Recent efforts have explored nanoparticle-based formulations to enhance its solubility and stability, as reported in the *International Journal of Pharmaceutics*. These innovations could significantly improve the therapeutic potential of (-)-pinoresinol in clinical settings.

In conclusion, (-)-pinoresinol (CAS: 81446-29-9) represents a multifaceted compound with substantial therapeutic potential. Its anti-inflammatory, antioxidant, and anticancer properties, coupled with advancements in synthesis and delivery technologies, position it as a promising candidate for future drug development. Continued research is essential to overcome existing limitations and fully harness its benefits in biomedicine.

• 177313-81-4(3,4-Furandimethanol, a4,2-bis(3,4-dimethoxyphenyl)tetrahydro-,(a4R,2S,3S,4R)-)
• 160550-16-3(3,4-Furandimethanol, α4,2-bis(3,4-dimethoxyphenyl)tetrahydro- (9CI))
• 487-39-8(Phillygenin)
• 16499-02-8(Diaeudesmin)
• 23397-47-9(Phenol,4-[(1R,3aS,4S,6aS)-4-(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2-methoxy-)
• 10061-38-8(Phenol,4,4'-[(1R,3aS,4S,6aS)-tetrahydro-1H,3H-furo[3,4-c]furan-1,4-diyl]bis[2-methoxy-(9CI))
• 160472-98-0(3-Furanmethanol,2-(3,4-dimethoxyphenyl)-4-[(3,4-dimethoxyphenyl)methoxymethyl]tetrahydro- (9CI))
• 148057-46-9(Membrin)
• 29395-87-7(Phenol,4-[(1S,3aR,4S,6aR)-4-(3,4-dimethoxyphenyl)tetrahydro-1H,3H-furo[3,4-c]furan-1-yl]-2-methoxy-)
• 163564-91-8(3-Furanmethanol,4-[ethoxy(4-hydroxy-3-methoxyphenyl)methyl]tetrahydro-a-(4-hydroxy-3-methoxyphenyl)-(9CI))