Додовисцин Н

Description

Dodoviscin H is a prenylated flavonol from Dodonaea viscosa (Hopbush, family Sapindaceae), which combines two types of side substituents in one molecule - a saturated hydroxylated chain and an unsaturated prenyl group. This double substitution makes it one of the largest representatives of the dodoviscin series in terms of molecular weight.

Basic Attributes

• CAS No: 1372527-39-3
• Chemical Formula: C26H30O7
• Molecular Weight: 454.5122
• Exact weight: 454.199158
• PSA Specifications: 116
• XLogP3: 4.84

Synonyms and nomenclature

• Dodoviscin H
• (-)-5,7-Dihydroxy-2-[4-hydroxy-3-(4-hydroxy-3-methylbutyl)-5-(3-methyl-2-buten-1-yl)phenyl]-3-methoxy-4H-1-benzopyran-4-one

Physico-chemical characteristics

• Density: 1.3±0.1 g/cm3
• Boiling point: 692.0±55.0 °C at 760 mm Hg. Art.
• Flash point: 233.1±25.0°C
• Refractive index: 1.639

Structural features

The chromone core with the (-) configuration carries a phenyl moiety at position 2 with a hydroxyl group, a saturated 4-hydroxy-3-methylbutyl side chain at position 4 of the ring and an unsaturated 3-methylbut-2-enyl (prenyl) group at position 5; in position 3 of the chromone there is a methoxy group. The combination of saturated and unsaturated isoprenoid moieties increases molecular weight and lipophilicity (XLogP3 4.84) ​​compared to mono-substituted dodoviscins I and J.

Substance class

It belongs to the doubly prenylated flavonols of Dodonaea viscosa - the most structurally saturated representatives of the series, along with dodoviscins A, I and J. The high refractive index (1.639) and elevated boiling point reflect the dense packing of the molecule due to bulky side chains.

Scope of application

Analytical standard for phytochemical studies: identification by HPLC-MS in complex extracts of Dodonaea viscosa, study of prenylation pathways of the flavonoid core with the formation of di-substituted structures, reference compound for the construction of mass spectrometric libraries of natural flavonoids. Not intended for medical or food use without further testing.

Related compounds

The series of dodoviscins from the plant Dodonaea viscosa includes mono-prenylated (I, J) and di-prenylated (H, A) structures, differing in the number of isoprenoid side chains on the chromone core. Dodoviscin H, combining saturated and unsaturated substituents, occupies an intermediate position in molecular weight between dodoviscin A and mono-substituted analogues, which makes it a convenient reference point for interpreting mass spectra of complex fractions.

Storage and transportation

Solid substance of laboratory purity. Store in the original hermetically sealed container, in a dry, cool place, protected from light at a temperature of 2–8 °C. A flash point of 233.1±25.0 °C indicates a low fire hazard of the substance under room storage conditions, however, when working with organic solutions, it is recommended to comply with the general fire safety requirements of the laboratory. Transport codes and hazard classes have not been established for the dump. When weighing samples, use an analytical balance and avoid prolonged contact of the powder with air and moisture.