340167-81-9

Basic information

• Product Name: (-)-3,3'-BisdeMethylpinoresinol
• Synonyms: (-)-3,3'-BisdeMethylpinoresinol
• CAS NO: 340167-81-9
• Molecular Formula: C18H18O6
• Molecular Weight: 330.33192
• Mol File: 340167-81-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 608.2±55.0 °C(Predicted)
• Appearance: /
• Density: 1.454±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.25±0.10(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: (-)-3,3'-BisdeMethylpinoresinol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-3,3'-BisdeMethylpinoresinol(340167-81-9)
• EPA Substance Registry System: (-)-3,3'-BisdeMethylpinoresinol(340167-81-9)

Safety Data

• Hazardous Substances Data: 340167-81-9(Hazardous Substances Data)

Usage

Description

(-)-3,3'-BisdeMethylpinoresinol is a compound that is formed as an impurity during the synthesis of Sesamin (S280500) metabolites. It is characterized by its antioxidant properties, which play a crucial role in protecting the liver from oxidative stress and damage.

Uses

Used in Pharmaceutical Industry:
(-)-3,3'-BisdeMethylpinoresinol is used as an antioxidant agent for the liver. Its antioxidant properties help in neutralizing harmful free radicals and reducing oxidative stress, which can lead to liver damage. This makes it a potential candidate for the development of pharmaceuticals aimed at treating liver-related conditions and promoting liver health.
Used in Nutraceutical Industry:
In the nutraceutical industry, (-)-3,3'-BisdeMethylpinoresinol can be utilized as an additive in dietary supplements and functional foods. Its antioxidant properties can contribute to the overall health benefits of these products, particularly in supporting liver function and general well-being.
Used in Cosmetics Industry:
(-)-3,3'-BisdeMethylpinoresinol may also find applications in the cosmetics industry, where its antioxidant properties can be harnessed to develop products that promote skin health and protect against environmental stressors, such as pollution and UV radiation. This can lead to the development of anti-aging and skin protection products with added benefits for the consumer.

Upstream product

• 133-03-9 sesamin 
• 60485-34-9 pinoresinol diglucoside 
• 133-03-9 (-)-asarinin 
• 133-04-0 episesamin 

Downstream Products

• 81446-29-9 (-)-pinoresinol 

Relevant articles and documents

Furofuran lignans as a new series of antidiabetic agents exerting α-glucosidase inhibition and radical scarvenging: Semisynthesis, kinetic study and molecular modeling

A new series of furofuran lignans containing catechol moiety were prepared from the reactions between lignans and a variety of phenolics. All 22 products obtained were evaluated against three different α-glucosidases (maltase, sucrase and Baker's yeast glucosidase) and DPPH radical. Of furofuran lignans evaluated, β-14, having two catechol moieties and one acetoxy group, was the most potent inhibitor against Baker's yeast, maltase, and sucrase with IC50 values of 5.3, 25.7, and 12.9 μM, respectively. Of interest, its inhibitory potency toward Baker's yeast was 28 times greater than standard drug, acarbose and its DPPH radical scavenging (SC50 11.2 μM) was 130 times higher than commercial antioxidant BHT. Subsequent investigation on mechanism underlying the inhibitory effect of β-14 revealed that it blocked Baker's yeast and sucrase functions by mixed-type inhibition while it exerted non-competitive inhibition toward maltase. Molecular dynamics simulation of the most potent furofuran lignans (4, α-8b, α-14, and β-14) with the homology rat intestinal maltase at the binding site revealed that the hydrogen bond interactions from catechol, acetoxy, and quinone moieties of furofuran lignans were the key interaction to bind tightly to α-glucosidase. The results indicated that β-14 possessed promising antidiabetic activity through simultaneously inhibiting α-glucosidases and free radicals.

Identification of the metabolites of episesamin in rat bile and human liver microsomes

Episesamin is an isomer of sesamin, resulting from the refining process of non-roasted sesame seed oil. Episesamin has two methylendioxyphenyl groups on exo and endo faces of the bicyclic skeleton. The side methylendioxyphenyl group was metabolized by cyt

First chemical synthesis of antioxidative metabolites of sesamin

The first chemical synthesis of two metabolites ((1R,2S,5R,6S)-6-(3,4- dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3,3,0]octane (SC-1) and (1R,2S,5R,6S)-2,6-bis(3,4-dihydroxyphenyl)-3,7-dioxabicyclo[3,3,0] octane (SC-2)) of sesamin was achieved by a simple two-step approach from sesamin. The approach consists of acetoxylation of the methylenedioxy moiety(ies) with lead(IV) tetraacetate and acid hydrolysis of the resulting hemiorthoester to SC-1 and SC-2.