Баккатин

Description

Baccatin (Baccatin, without a number suffix) is a natural triterpenoid of the D:A-freedooleanane series with an epidioxide bridge in the structure, an isomer of (14ξ,17ξ)-14,17-epidioxy-28-nor-D-freedo-5α-olean-15-en-2α,3β-diol. Despite the similar name, the compound does not structurally belong to taxane diterpenoids (baccatin III, IV, VI) - it is a representative of a completely different class of natural triterpenes of the olean series.

Basic Attributes

• CAS No: 66107-60-6
• Chemical formula: C29H46O4
• Molecular weight: 458.7
• Exact weight: 458.33960994

Connection class

Triterpenes of the D:A-freedooleanane series are formed by rearrangement of the classical oleanane skeleton and are characterized by the migration of methyl groups between rings C and D. The presence of a peroxide (epidioxy-) bridge between the C14 and C17 atoms is a rare and chemically significant structural feature that distinguishes baccatin from most related triterpene diols.

Scope of application

Baccatin, as a representative of triterpene peroxides of plant origin, is considered in studies of natural compounds with potential cytotoxic and antiparasitic activity - the peroxide functional group is characteristic of a number of biologically active natural products (by analogy with artemisinin, which also contains an endoperoxide bridge). The compound is used as an object for comparative structural analysis of triterpene peroxides of plant origin.

Physico-chemical interpretation

The molecular formula C29H46O4 with four oxygen atoms corresponds to the diol and peroxide functionality of the molecule. The molecular weight of 458.7 is typical of skeletal C29–C30 triterpenoids, confirming that the compound belongs to the broad class of triterpenes of plant origin.

Storage and handling

There is no data on hazard classification, transport codes and GHS phrases for baccatin in open sources and in the original dump - the substance is supplied as an analytical standard of plant origin for laboratory research in small quantities. Given the presence of a peroxide group, the compound may be sensitive to heat and light, so storage in a cool, dry place, protected from light, in an airtight container, away from heat sources is recommended. Wear gloves and use respiratory protection when working with powder.

Difference from taxane baccatins

It is important not to confuse this compound with the taxane diterpenoids of the same name - baccatin III, baccatin IV and baccatin VI, isolated from yew and serving as precursors to paclitaxel. The coincidence of the name reflects only the general origin of the term in the chemistry of natural terpenoids, but not the structural relationship: baccatin belongs to the oleanan, and not the taxane series of triterpenes.

Identification

The CAS number 66107-60-6 and the chemical formula C29H46O4 serve as the main parameters for unambiguously identifying the compound and distinguishing it from taxane baccatins when working with natural product databases.