ДигидрозезаМин

Identification

Dihydrosesamin (English: DihydrosesaMin, CAS 83708-70-7) is a furan-type lignan, a derivative of sesamin. The systematic name is (2R,3S,4S)-2-(1,3-benzodioxol-5-yl)-4-(1,3-benzodioxol-5-ylmethyl)tetrahydro-3-furanmethanol. Chemical formula C20H20O6. The molecule is built from two phenylpropanoid fragments closed in a furan (tetrahydrofuran) ring - a bicyclic skeleton characteristic of furanolignans, common in sesamin and its derivatives.

Molecular parameters

• Molecular Weight: 356.3692
• Exact weight: 356.12598835
• PSA specifications: 66.38000
• XLogP3: 2.68270

Physico-chemical properties

• Melting point: 97–99 °C
• Appearance: Crystalline solid (typical of this group of lignans)

Scope of application

Sesame seeds (Sesamum indicum) are the main natural raw material, rich in lignans: sesamin, sesamolin and their derivatives, which include dihydrosesamine. The plant is cultivated mainly in the tropical and subtropical regions of Asia and Africa, and the seeds and the oil obtained from them are a traditional component of the cuisine and cosmetics of these regions, which explains the interest of phytochemistry in the full lignan profile of raw materials. Like related lignans, the substance is being studied in the context of antioxidant cell protection, anti-inflammatory effects and liver support; such compounds are being considered in studies of the bioavailability and metabolic pathways of lignans for nutraceutical and pharmaceutical development. It is commercially supplied as a reference standard for analytical chemistry and scientific research - identification and quantitative determination of lignans in plant materials and food extracts by chromatography methods. Sesamin, the closest structural analogue, has been widely studied as an inhibitor of delta-5-fatty acid desaturase and has been the subject of research into its effect on lipid metabolism; dihydro derivatives, including dihydrosesamine, are used as standards when clarifying the structure-function relationships within this group of lignans. Cold-pressed sesame oil traditionally contains the largest proportion of native lignans, while during refining and heat treatment their profile partially changes - part of the sesamin and sesamolin is converted into derivatives, including dihydroforms, which makes such compounds useful indicators of the degree of oil processing when monitoring the quality of food raw materials.

Security and storage

There are no data on hazard classification, transport codes and storage conditions in the dump - for highly specialized phytochemical standards of this kind, public hazard data are usually not established by the manufacturer. For lignan standards, which are crystalline solids with a melting point of approximately 98°C, standard practice is to store them in an airtight container in a cool, dry place, away from light and away from oxidizing agents and sources of moisture. When packing the powder, use gloves and avoid the formation of dust; After sampling, the container should be immediately resealed to limit contact of the crystalline substance with air moisture.