61597-55-5

Basic information

• Product Name: 15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene
• Synonyms: 15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene;15,16-Epoxy-12-hydroxylabda- 8(17),13(16),14-triene
• CAS NO: 61597-55-5
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.451
• Mol File: 61597-55-5.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene(CAS DataBase Reference)
• NIST Chemistry Reference: 15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene(61597-55-5)
• EPA Substance Registry System: 15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene(61597-55-5)

Safety Data

• Hazardous Substances Data: 61597-55-5(Hazardous Substances Data)

Usage

General Description

15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene is a naturally occurring diterpene chemical compound. It is characterized by its unique structure, containing a 15,16-epoxy group, a 12R-hydroxyl group, and a labda-8(17),13(16),14-triene skeleton. 15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene has been found in various plants and has been investigated for its potential pharmacological and medicinal properties. Research has suggested that 15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene may have anti-inflammatory, anti-tumor, and anti-microbial activities. Due to its complex structure and potential biological activities, this compound presents an interesting target for further research and development in the field of natural product chemistry and drug discovery.

Upstream product

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Downstream Products

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Relevant articles and documents

Synthesis of (+)-zerumin B using a regioselective singlet oxygen furan oxidation

(Chemical Equation Presented) A short and efficient synthesis of the antitumor diterpenoid (+)-zerumin B has been accomplished starting from (+)-sclareolide. At the heart of the synthetic strategy lies the regioselective formation of the α-substituted γ-hydroxybutenolide moiety of zerumin B. This was achieved by means of a [1,4] O→C triisopropylsilyl migration followed by singlet oxygen (1O2) oxidation of the resulting 2-triisopropylsilyl-3-(α-hydroxy)alkylfuran.

Trypanocidal labdane diterpenoids from the seeds of Aframomum aulacocarpos (Zingiberaceae)

Two novel labdane type diterpenoids, 8β(17)-epoxy-14,15,16-trihydroxylabd-12(E)-ene (aulacocarpin C) and 15,16-epoxy-14ξ,16ξ-dimethoxylabda-8(17),12-(E)-diene (aulacocarpin D) together with the known aulacocarpin A and B; 14,15-epoxy-8(17),12(E)-labdadien-16-al, coronarin E, and 15,16-epoxy-12β-hydroxy-labda-8(17)-13(16),14-triene were isolated from the seeds of Aframomum aulacocarpos. To the best of our knowledge, the last compound was isolated from a natural source for the first time. Acid hydrolysis of aulacocarpin D led to another new labdane type diterpenoid, 15,16-epoxy-12β-methoxylabda-8(17)-13(16),14-triene. The structures of all compounds were established on the basis of their spectroscopic data. These new compounds exhibit moderate trypanocidal activity.

Synthesis and stereochemistry of the antitumor diterpenoid (+)-zerumin B

Starting from commercially available (+)-sclareolide, the first synthesis of zerumin B was achieved by a concise, highly efficient pathway featuring stereoselective addition of a new silyloxyfuryltitanium reagent to an aldehyde intermediate and silyloxyfuran oxyfunctionalization as key steps. The synthesis established the relative and absolute configuration of zerumin B along with its identity with a purportedly new diterpenoid isolated from the plant Renealmia alpinia.