Тайванин-с

Description

Taiwanin C is a natural lignan isolated from Taiwania cryptomerioides. According to the structural classification, it is furonaphdioxol: a furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one framework bearing a 1,3-benzodioxol-5-yl substituent at position 5. The compound was also recorded in Cleistanthus collinus and in plants of the genus Eleutherococcus, and was isolated from the root of Acanthopanax chiisanensis.

Basic Attributes

• CAS No.: 14944-34-4
• Chemical formula: C20H12O6
• Molecular weight: 348.3 g/mol
• Exact (monoisotopic) mass: 348.06388810
• Topological polar surface area: 63.2 Ų
• XLogP3: 3.8
• Number of hydrogen bond acceptors: 6
• Number of rotating links: 1
• Number of heavy atoms: 26
• Structural complexity index: 581
• Number of covalently bonded units: 1
• The structure is canonized

Physico-chemical properties

• Melting point: 273–275 °C

A single rotating bond with 26 heavy atoms means an almost rigid molecule: only the fragment connecting the benzodioxole ring to the main framework is mobile. Hence the high melting point - flat, rigid molecules are packed tightly into the crystal. The lipophilicity of XLogP3 3.8 with a polar surface of 63.2 Ų indicates poor solubility in water and good solubility in dimethyl sulfoxide and chlorinated solvents.

Biological activity

• potential inhibitor of cyclooxygenase-2 (COX-2) expression - a property identified for the compound after isolation from Taiwania cryptomerioides
• antitumor agent
• platelet aggregation inhibitor
• plant metabolite

Scope of application

• reference substance for phytochemical analysis of lignans
• standard for chromatographic methods for the determination of lignans in plant materials
• object of research on anti-inflammatory and antitumor activity

Notes on card data

The source data contains machine artifacts, which are corrected in the description.

• The line “Exact mass: 348.31” contradicts the monoisotopic mass 348.06388810 given in the same card. The correct value is 348.06388810; the value 348.31 is a distortion of the molecular weight 348.3
• The entry “Grid Entry Terms: Taiwanese C” is a machine translation of the MeSH Entry Terms: Taiwanin C phrase, that is, a list of entry terms into the MeSH thesaurus. Has nothing to do with the properties of the substance
• The entry “Compound is canonicalized: Yes” is a translation of the database service attribute Compound Is Canonicalized, meaning bringing the structure to canonical form

Storage and handling

GHS classification, transport codes, labels and toxicity data are not included in the card - they are taken from the batch’s safety data sheet. The product is supplied in small portions as a research reagent. Store in a tightly closed container, protect from light and heat; Prepare solutions immediately before use. Weighing should be carried out under a hood, wearing gloves and safety glasses. Taking into account the declared antitumor activity, access to the substance is limited, and waste is collected separately.