Логановая кислота

Description

Loganic acid is an iridoid glycoside: a cyclopenta[c]pyran framework with a carboxyl group at C-4 and a β-D-glucopyranose residue at C-1. The second accepted spelling is loganinic acid. In plants, it serves as the immediate precursor of loganin, from which secologanin is further formed, a common building block of monoterpene indole alkaloids. It accumulates in the fruits of dogwood (Cornus mas), in the raw material of Cornus officinalis, in gentians and honeysuckles. Catalog section - iridoids.

Basic Attributes

• CAS No.: 22255-40-9
• Chemical formula: C16H24O10
• Molecular weight: 376.36
• Exact weight: 376.36
• EU number: 244-875-9
• PSA Specifications: 166
• XLogP3: −2.49

Physico-chemical characteristics

• Density: 1.6 ± 0.1 g/cm³
• Boiling point: 646.3 ± 55.0 °C at 760 mm Hg. Art.
• Flash point: 235.6 ± 25.0 °C
• Refractive index: 1.634
• Vapor pressure: 1.97 × 10⁻¹⁹ mm Hg. Art. at 25 °C
• Storage conditions: −20 °C

A negative XLogP3 value (−2.49) and a polar surface of 166 characterize a hydrophilic substance: it dissolves well in water and methanol and poorly in non-polar solvents. The vapor pressure is practically zero, the substance is non-volatile. The calculated boiling and flash points are given formally: the glycoside decomposes long before these values.

Biochemical role and studied effect

Loganic acid occupies a key position in the iridoid pathway: its methylation produces loganin, oxidative opening of the cyclopentane ring produces secologanin, and the condensation of secologanin with tryptamine opens the way to the indole alkaloids vinca and rauwolfia. As an individual substance, it is studied for anti-inflammatory and antioxidant activity and serves as a chemotaxonomic marker of iridoid-containing raw materials.

Scope of application

• reference standard for standardizing raw materials of dogwood, dogwood and gentians
• marker in HPLC and LC-MS for determining iridoids
• substrate and standard in biochemical work on the secologanin biosynthesis pathway
• reagent for preclinical testing of anti-inflammatory and antioxidant effects

Safety information, storage and transportation

• Transport codes: NONH for all modes of transport - the substance is not classified as dangerous goods
• WGK Germany: 3

Storage at −20 °C in a tightly closed container, in the dark and without moisture: the glycosidic bond is cleaved by acids and glycosidases. Solutions of water or methanol are aliquoted and frozen. Water hazard class 3 requires preventing the substance and wash water from entering sewers and water bodies. The product card does not contain hazard statements and precautionary measures according to the GHS; gloves and safety glasses are used during work.