81446-29-9

Basic information

• Product Name: (-)-PINORESINOL
• Synonyms: (-)-PINORESINOL
• CAS NO: 81446-29-9
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.39
• Mol File: 81446-29-9.mol
• Article Data: 35

Chemical Properties

• Melting Point: 119-120 °C
• Boiling Point: 556.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.287±0.06 g/cm3(Predicted)
• PKA: 9.54±0.35(Predicted)
• CAS DataBase Reference: (-)-PINORESINOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-PINORESINOL(81446-29-9)
• EPA Substance Registry System: (-)-PINORESINOL(81446-29-9)

Safety Data

• Hazardous Substances Data: 81446-29-9(Hazardous Substances Data)

Usage

General Description

(-)-Pinoresinol is a natural lignan compound found in various plants such as sesame seeds, olive oil, and flaxseed. It is known for its antioxidant properties and potential health benefits. Studies have shown that (-)-pinoresinol may have anti-inflammatory, anti-cancer, and anti-diabetic effects. It has also been investigated for its potential use in the treatment of cardiovascular diseases and neurological disorders. Furthermore, (-)-pinoresinol has been found to have antimicrobial properties, making it a potential candidate for use in food preservation and as a natural antimicrobial agent. Overall, (-)-pinoresinol is a promising chemical with diverse potential applications in health, nutrition, and food science.

Upstream product

• 101391-02-0 Versicoside 
• 651779-99-6 (1R,2R,5R,6S)-2-(4-methanesulfonyloxy-3-methoxy)phenyl-6-(4-methanesulfonyloxy-3-methoxy)phenyl-3,7-dioxabicyclo[3.3.0]octane 
• 52200-05-2 4-methanesulfonyloxy-3-methoxybenzaldehyde 
• 1135-24-6 3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 458-35-5 coniferol 
• 1135-24-6 (E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid 
• 458-35-5 coniferal alcohol 
• 526-06-7 eudesmin 
• 487-36-5 (+/-)-pinoresinol 
• 526-06-7 eudesmine 
• 526-06-7 (+/-)-dimethylpinoresinol 
• 340167-81-9 3,3-bis-demethylpinoresinol 
• 149-73-5 trimethyl orthoformate 
• 651779-84-9 1-(4-methanesulfonyloxy-3-methoxyphenyl)prop-2-en-1-ol 

Downstream Products

• 1217544-22-3 (+)-eudesmin 
• 526-06-7 eudesmin 
• 487-36-5 (+)-epipinoresinol 
• 67560-65-0 2,6-bis-(4-benzyloxy-3-methoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane 
• 76874-00-5 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(1S,3aR,4S,6aR)-4-(4-hydroxy-3-methoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1-yl]-2-methoxy-phenoxy}-tetrahydro-pyran-3-yl ester 
• 24404-51-1 (+/-)-pinoresinol diacetate 
• 3688-23-1 (-)-secoisolariciresinol 
• 5502-29-4 9,9'-Diacetoxy-guaja-cyclolign-7'-en-diacetat 
• 526-06-7 eudesmine 
• 526-06-7 (+/-)-dimethylpinoresinol 
• 3508-52-9 tremellin 
• 60102-89-8 (+)-epipinoresinol dimethyl ether 
• 487-39-8 (+)-pinoresinol monomethyl ether 
• 24404-49-7 (+/-)-Pinoresinol-4'-O-β-D-monoglucoside 

Relevant articles and documents

Lignans from Lepidium meyenii and Their Anti-Inflammatory Activities

Meyeniines A–C (1–3), three new lignans, two known neolignans (4–5), and three known lignans (6–8) were isolated from the rhizomes of Lepidium meyenii. Their structures were identified by comprehensive spectroscopic analyses and computational methods. Compound 1 represents a unique lignan featuring an aromatic ring migration. Compounds 2 and 4–6 were analyzed by chiral HPLC column as enantiomers. Biological evaluation revealed that compound 8 could inhibit IL-6 production in lipopolysaccharide (LPS) induced RAW264.7 cells in a dose-dependent manner.

Pinoresinol-lariciresinol reductase: Substrate versatility, enantiospecificity, and kinetic properties

Two western red cedar pinoresinol-lariciresinol reductase (PLR) homologues were studied to determine their enantioselective, substrate versatility, and kinetic properties. PLRs are downstream of dirigent protein engendered, coniferyl alcohol derived, stereoselective coupling to afford entry into the 8- and 8′-linked furofuran lignan, pinoresinol. Our investigations showed that each PLR homolog can enantiospecifically metabolize different furofuran lignans with modified aromatic ring substituents, but where phenolic groups at both C4/C4′ are essential for catalysis. These results are consistent with quinone methide intermediate formation in the PLR active site. Site-directed mutagenesis and kinetic measurements provided additional insight into factors affecting enantioselectivity and kinetic properties. From these data, PLRs can be envisaged to allow for the biotechnological potential of generation of various lignan skeleta, that could be differentially “decorated” on their aromatic ring substituents, via the action of upstream dirigent proteins.

Isolation of enantiomeric furolactones and furofurans from Rubus idaeus L. with neuroprotective activities

A phytochemical study on the fruits of Rubus idaeus L. (Rosaceae) yielded eight pairs of enantiomeric lignans, including one undescribed furolactone named (?)-idaeusinol A and six undescribed furofuran derivatives named (+/?)-idaeusinol B–D. The structures of these isolated compounds were elucidated by spectroscopic analyses and a combination of computational techniques including gauge-independent atomic orbital (GIAO) calculation of 1D NMR data and TD-DFT calculation of electronic circular dichroism (ECD) spectra. Bioactivity screenings suggested that (+)-idaeusinol D exhibited the most significant protective effect against H2O2-induced neurotoxicity at the concentration of 25 μM. In contrast, (?)-idaeusinol D, as the enantiomer of (+)-idaeusinol D, showed no effect against H2O2-induced neurotoxicity at both 25 and 50 μM concentration.