Одоринол

Description

Odorinol is a natural diamide isolated from Aglaia odorata. Structurally, it is an aminopyrrolidine diamide: the pyrrolidine ring is acylated with cinnamic acid in the E-configuration, and the amino group at C-2 is linked to the 2-hydroxy-2-methylbutyric acid residue. Stereochemistry established for (−)-odorinol and published in Phytochemistry in 1982. In catalogs, the substance is listed under alkaloids; it is more correct to classify it as an amide alkaloid.

Basic Attributes

• CAS No: 72755-22-7
• Gross formula: C₁₈H₂₄N₂O₃
• Molecular Weight: 316.401
• Accurate weight: 316.178680
• PSA specifications: 69.6
• XLogP3: 1.55
• Density: 1.2 ± 0.1 g/cm³
• Boiling point: 588.6 ± 50.0 °C at 760 mm Hg. Art.
• Flash point: 309.8 ± 30.1 °C
• Refractive index: 1.583
• Systematic name: (2S)-2-hydroxy-2-methyl-N-[(2R)-1-[(E)-1-oxo-3-phenyl-2-propenyl]pyrrolidin-2-yl]butanamide

Activity studied

Odorinol is described as an antileukemic diamide: it is with this property that its first isolation from Aglaia odorata is associated. In a two-stage carcinogenesis test on mouse skin, where 7,12-dimethylbenz[a]anthracene (DMBA) was the initiator and 12-O-tetradecanoylphorbol-13-acetate (TPA) was the promoter, the compound suppressed both stages—initiation and promotion. This direction is being studied in the context of tumor chemoprevention.

Scope of application

• reference standard for HPLC and LC-MS for the analysis of Aglaia extracts and standardization of plant materials
• instrumental connection in oncology research: models of leukemia and two-stage skin carcinogenesis
• object of work on the chemistry of natural diamides and the connection “stereochemistry - activity”

Storage and handling

Fine reagent, supplied in small packages. Store in a tightly closed container, away from light and moisture. Working solutions are prepared in DMSO, methanol or acetonitrile. Wear gloves and safety glasses to avoid dust.