Мелилотозид

Description

Melitoside is a phenolic O-glycoside, 2-O-β-D-glucoside of trans-o-coumaric (o-hydroxycinnamic) acid. Isolated from sweet clover, primarily from Melilotus officinalis and M. neapolitana. In the living plant it is the bound, inactive form of coumaric acid. When tissues wither and destroy, the enzyme splits off glucose, the released trans-acid is isomerized under the influence of UV into the cis-form and locked into a lactone - coumarin is formed, which gives sweet clover the smell of fresh hay. For this reason, melitoside is considered a biogenetic precursor of coumarin.

Basic Attributes

• CAS No: 618-67-7 (additional registrations: 15044-27-6, 30677-12-4)
• Gross formula: C15H18O8
• Molecular Weight: 326.301
• Exact weight: 326.30
• UNII: M87W7715UB
• PSA Specs: 137
• XLogP3: −0.4

Structure and nomenclature

• (2E)-3-[2-(β-D-glucopyranosyloxy)phenyl]-2-propenoic acid
• trans-melilotoside, trans-o-hydroxycinnamic acid glucoside
• Class: phenolic acid glycosides, aglycone - o-coumaric acid
• Negative XLogP3 reflects the hydrophilicity of the sugar residue: the substance gravitates towards aqueous-alcoholic extracts

Scope of application

• standard sample for chromatographic control of sweet clover raw materials and preparations based on it
• marker of the coumarin-forming ability of a batch of raw materials - based on the glycoside content, one can judge how much coumarin the raw material will produce during drying
• reagent in phytochemical works: antiparasitic activity and ability to quench the DPPH radical are described

Safety Information

• WGK Germany: 3
• Safety instructions: 26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical attention.
• Tags: Xi, irritant

Storage and handling

Wear gloves and safety glasses and avoid dust when hanging. Hazard class for the aquatic environment WGK 3 prohibits the discharge of solutions and washes into the sewer - the remains are collected and handed over to a licensed operator.