Ацетонид Агатарезинола

Description

Agataresinol acetonide is a derivative of the norlignan agataresinol, obtained by protecting the vicinal diol with an isopropylidene (acetonide) group. CAS 800389-33-7, chemical formula C20H22O4, molecular weight 326.38628, exact weight 326.151794. Systematic name: 4-[(1E,3S)-3-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-3-(4-hydroxyphenyl)-1-propen-1-yl]phenol. Norlignans, which include the original agataresinol, are characteristic of coniferous species, in particular the genus Sequoia.

Basic Attributes

• CAS No: 800389-33-7
• Chemical formula: C20H22O4
• Molecular weight: 326.38628
• Exact weight: 326.151794

Physico-chemical characteristics

• PSA specifications: 58.9
• XLogP3: 3.18
• Density: 1.2±0.1 g/cm3
• Boiling point: 484.8±40.0 °C at 760 mm Hg. Art.
• Flash point: 247.0±27.3°C
• Refractive index: 1.618

Construction and receipt

The molecule is the product of ketalization of the 1,2-diol side chain moiety of agateresinol with acetone to form a 1,3-dioxolane ring (acetonide). Such protection is used in the synthetic chemistry of norlignans to temporarily block the side chain hydroxyl groups while maintaining the reactivity of the phenolic hydroxyls of the aromatic rings. Two para-hydroxyphenyl fragments connected by a propene bridge with a dioxolane substituent determine the structural affinity of the compound with the class of stilbenoid norlignans of conifers.

Scope of application

It is used as a synthetic intermediate and reference standard in the study of norlignans from coniferous plants, including the development of methods for the protection and deprotection of diol fragments in the synthesis of natural norlignans and related phenolic compounds.

Storage and handling

The substance is stored in the form of a dry powder or oil in a tightly closed container, protected from light and moisture, preferably at a low temperature (2–8 °C), since the acetonide protecting group is sensitive to hydrolysis in an acidic aqueous environment. When working, use gloves and respiratory protection, avoid contact with acids and long-term storage in an open aquatic environment.

Related connection

The original agataresinol (unprotected form, without an acetonide group) is a related compound of the same structural series of norlignans, characterized by the presence of a free 1,2-diol instead of a cyclic acetal and a lower molecular weight. In coniferous wood, norlignans of this series, including agataresinol, are involved in coloring heartwood and protecting sapwood from microbial contamination, so protected derivatives like acetonide are used as stable model compounds when studying their chemistry and biosynthesis without the risk of premature oxidation of the side chain. The compound was first described in the context of the chemistry of the norlignans of the order Araucariales in 1966; A complete stereoselective synthesis of agataresinol and related coniferous norlignans was performed in 1978, which laid the methodological basis for the subsequent preparation of protected derivatives, including the real acetonide.