Диацетат гониодиола

Identification

Goniodiol diacetate is an acylated (diacetate) derivative of the natural styrylactone goniodiol. The basic compound of this series is isolated from plants of the genus Goniothalamus of the Anonaceae family, in particular from Goniothalamus sesquipedalis. English name of the substance is Goniodiol diacetate, CAS number 136778-40-0, chemical formula C21H35IO5. The structure contains an iodine atom - this distinguishes the commercial form from simple goniodiol diacetate and suggests that this is an iodinated synthetic analogue, used as an intermediate in the study of styrylactones and their analogues.

Physico-chemical characteristics

• Molecular Weight: 494.40407
• Exact weight: 318.11
• PSA specifications: 78.9 Å2
• XLogP3: 2.1
• Density (predicted): 1.236±0.06 g/cm3
• Boiling point (predicted): 386.4±12.0 °C

The calculated PSA value of 78.9 Å2 indicates a moderate polarity of the molecule, with contributions from two ester (acetate) groups and a lactone ring moiety. XLogP3 2.1 indicates moderate lipophilicity: the compound occupies an intermediate position between the water-soluble goniodiol and its more hydrophobic ester derivatives. Density and boiling point are given by calculation method (predicted values, marked in the dump as predicted), since no experimental data on the pure drug was found in open sources. The difference between the molecular weight (494.4) and the exact mass indicated in the dump (318.11) attracts attention - this may be a consequence of the fact that the exact mass is calculated for a fragment ion or related structure without part of the substituents; When working with this indicator, it is worth double-checking it against the passport of a specific batch.

Substance class and origin

The compound belongs to the group of styryllactones - 5,6-dihydro-2H-pyran-2-one derivatives with a phenyl substituent, characteristic of the genus Goniothalamus. These secondary metabolites are being actively studied as sources of structures that are selectively cytotoxic for tumor cells. Diacetylation of the hydroxyl groups of goniodiol is used by chemists as a way to protect reactive OH groups in the synthesis of analogues and in studying the structure dependence of cytotoxic activity (SAR) in the styrylactone series: by varying the substituents while maintaining the lactone core, researchers evaluate the contribution of each functional group to the biological effect.

Scope of application

• reagent for laboratory synthesis and modification of styrylactones
• reference compound for chromatographic and spectral analysis of natural goniodiols
• intermediate in structure-activity studies of cytotoxic lactones of Goniothalamus
• object of comparison when studying the influence of acylation and halogenation on the physicochemical properties of styrylactones

No direct data on the industrial or agricultural use of goniodiol diacetate has been found in open sources - the compound is used mainly for research purposes, in laboratories of organic synthesis and pharmacological screening of natural compounds.

Storage and transportation

There is no information about the hazard class, transport codes and storage conditions in the dump; data on regulated storage temperatures and GHS labeling have not been found and are not published by the reagent manufacturers. Until official information is received, a general procedure for handling organic reagents for laboratory use is recommended: sealed containers, cool dry place, protection from light and moisture, isolation from strong oxidizing agents and reducing agents. When working with poorly studied synthetic intermediates, it is advisable to use personal protective equipment - gloves, goggles, exhaust ventilation - as if the toxicity profile was unfavorable until one's own test data are available.