Дафмакрин

Description

Dafmacrine is an alkaloid of the Daphniphyllum group, obtained by directed chemical transformation of the related alkaloid dafmacropodine. Both compounds are isolated from Daphniphyllum macropodum Miq. and are connected by a direct biogenetic and synthetic chain established in the classical work on structural chemistry of this kind.

Basic Attributes

• CAS No.: 19775-48-5
• Chemical Formula: C32H49NO4
• Molecular weight: 511.73600
• Exact weight: 511.366150
• PSA Specifications: 55.84000
• XLogP3: 6.64

Physico-chemical characteristics

• Density: 1.2±0.1 g/cm3
• Boiling point: 588.8±25.0 °C at 760 mm Hg. Art.
• Flash point: 309.9±23.2°C
• Refractive index: 1.568

The values ​​of density, boiling point and flash point are calculated (predicted); melting point and solubility data have not been published in open sources.

Structure and relationship

The molecular formula C32H49NO4 differs from the formula of dafmacropodine (C32H51NO4) by two hydrogen atoms, which corresponds to additional unsaturation or cyclization formed during the conversion of one alkaloid to another. Other related structures, dapmacrimines and dapmacromines, have also been isolated from the same plant species.

Scope of application

It is used as an analytical standard and object for studying the structural chemistry and biogenesis of daphniphyllum alkaloids, as well as a model compound for studying intramolecular cyclization reactions in total synthesis. Reagent for Research Use Only (RUO).

Storage and transportation

Store in an airtight container in a dry, dark, cool place, away from heat sources - flash point 309.9 °C. Work using gloves and safety glasses in a fume hood, avoiding dust formation.

Implications for structural chemistry

The dafmacropodine–dafmacrine pair demonstrates how a single chemical modification of the framework—the loss of two hydrogen atoms through additional cyclization or unsaturation—transforms one natural Daphniphyllum alkaloid into another. Such transformations are widely used in constructing biogenetic maps of the genus and in developing routes for the total synthesis of related Daphniphyllum scaffolds, including dapmacrimines and dapmacromines isolated from the same plant species.

Quality control

Identity is confirmed by NMR and mass spectrometry based on the formula C32H49NO4, molecular weight 511.736 and exact mass 511.36615.

Place in the Daphniphyllum alkaloid family

Daphmacrine and dafmacropodine belong to the large family of Daphniphyllum alkaloids (more than three hundred described structures), united by a common biogenetic origin from squalene. Since the 1960s, such “precursor-derivative” pairs have served as reference points in constructing a complete biogenetic map of the genus and in developing a methodology for the total synthesis of complex polycyclic frameworks.