Агатарезинол

Description

Agataresinol is a natural norlignan isolated from conifers, in particular from evergreen redwood (Sequoia sempervirens). CAS 1968234 (databases also indicate 23248-82-0), chemical formula C17H18O4, molecular weight 286.327, exact weight 286.32. Stereochemical form (2S,3S,4E). Systematic name: (2S,3S,4E)-3,5-bis(4-hydroxyphenyl)-4-pentene-1,2-diol.

Basic Attributes

• CAS No: 1968234 (ext. 23248-82-0)
• Chemical formula: C17H18O4
• Molecular weight: 286.327
• Exact weight: 286.32

Physico-chemical characteristics

• PSA Specifications: 80.9
• XLogP3: 2.3
• Melting point: 105–116 °C

Compound class and origin

Agataresinol belongs to norlignans - phenolic compounds, structurally related to lignans, but with a side chain shortened by one carbon atom. The molecule is built from two para-hydroxyphenyl fragments connected by a pentenediol bridge with a double bond in position 4 (E-configuration) and a vicinal diol in positions 1 and 2. Norlignans of this type are characteristic of wood and bark of coniferous species, primarily of the genus Sequoia, where they perform protective and antioxidant functions as part of extractives.

Role in wood

In addition to evergreen sequoia, agataresinol has been identified in the wood of Cryptomeria japonica, New Zealand agathis (Agathis australis) and giant Wellingtonia (Sequoiadendron giganteum), and has also been isolated from the heartwood of metasequoia (Metasequoia glyptostroboides). Immunohistochemical methods have shown that in the core wood of cryptomeria the compound is localized precisely in the cells of the ray parenchyma. Along with other norlignans, agataresinol is involved in the coloring of heartwood and the protection of conifer sapwood from microbial infection. The chemistry of this compound was first described in a study of the order Araucariales in 1966, and its stereoselective total synthesis, along with other characteristic coniferous norlignans, was performed in 1978.

Scope of application

The compound is used as a phytochemical reference standard in studying the phenolic composition of coniferous extracts and as an object for studying the antioxidant activity of plant-derived norlignans. It also serves as a starting material for the preparation of protected derivatives, such as agataresinol acetonide, used in the synthetic chemistry of this class of compounds.

Storage and handling

The crystalline substance is stored in a tightly closed, light-proof container, in a cool, dry room, protected from direct light, since the phenolic hydroxyls and the conjugated double bond of the molecule are sensitive to oxidation in air. When packing and weighing, use gloves, avoid the formation and inhalation of dust, and store separately from oxidizing agents.

Related connection

Agataresinol acetonide (CAS 800389-33-7) is a derivative with a vicinal diol protected in the form of a dioxolane ring, used as an intermediate in the synthesis and modification of norlignans of this series.