Дафнин

Description

Daphnin is a coumarin glycoside, 7-β-D-glucopyranoside of dafnetin (8-hydroxycoumarin-7-O-glucoside). Isolated from the whole plant of Daphne odora (scented wolfwort) and other species of the genus Daphne; In traditional Chinese medicine, raw materials were used as an antipyretic. Biosynthetically, it is formed from dafnetin - dihydroxycoumarin - by enzymatic glycosylation with the participation of O-dihydroxycoumarin-7-O-glucosyltransferase, and upon hydrolysis it is able to return back to dafnetin.

Basic Attributes

• CAS No: 486-55-5 (related CAS: 1329-91-5, 22059-07-0)
• Chemical formula: C15H16O9
• Molecular weight: 340.28200
• Exact weight: 340.28
• UNII: K4REW3G17G
• DSSTox ID: DTXSID80197563
• PSA Specifications: 149.82000
• XLogP3: −0.6

Physico-chemical characteristics

• Density: 1.679 g/cm3
• Melting point: 216–217 °C
• Boiling point: 670 °C at 760 mm Hg. Art.
• Flash point: 252.4 °C
• Refractive index: 1.689
• Vapor pressure: 7.24 × 10 to the power of −19 mm Hg. Art. at 25 °C (virtually non-volatile)

Biological activity

Daphnin exhibits antibacterial activity and is one of the main biologically active coumarins of the Daphne genus. Modulates biochemical pathways associated with oxidative stress and inflammation. It is important to consider that plants of the genus Daphne contain strong irritants that can cause inflammation of the skin and mucous membranes upon contact with raw materials.

Scope of application

It is used as an analytical standard for coumarin glycosides and an object for studying the antibacterial, anti-inflammatory and antioxidant activity of natural compounds, as well as in studying the pathways of coumarin biosynthesis (glycosylation of dafnetin). The reagent is for research use only (RUO), not for medical use.

Storage and transportation

Store in an airtight container in a dry, dark, cool place, away from heat sources - taking into account the melting point of 216–217 °C and flash point of 252.4 °C. Wear gloves and safety glasses, avoid dust formation and contact with skin and mucous membranes.

Place in phytochemistry of the genus Daphne

The coumarins of the genus Daphne (dafnetin, daphnin, umbelliferone and their derivatives, including the biscoumarin daphnoretin from the related genus Wikstroemia) are the subject of ongoing interest in phytochemistry due to their combination of antibacterial, antioxidant and anti-inflammatory activities. The glycoside form, daphnine, is noticeably more polar (PSA 149.82 versus typical aglycone values), more soluble in water, and is considered the transport form of dapnetin in the plant.

Analytical identification

The identity and purity of the sample is confirmed by HPLC and spectral methods (NMR, mass spectrometry), based on the formula C15H16O9, molecular weight 340.282 and exact mass 340.28.