216011-55-1

Basic information

• Product Name: 15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene
• Synonyms: 15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene
• CAS NO: 216011-55-1
• Molecular Formula: C₂₀H₃₀O₂
• Molecular Weight: 302.451
• Mol File: 216011-55-1.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene(CAS DataBase Reference)
• NIST Chemistry Reference: 15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene(216011-55-1)
• EPA Substance Registry System: 15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene(216011-55-1)

Safety Data

• Hazardous Substances Data: 216011-55-1(Hazardous Substances Data)

Usage

Description

15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene is a natural chemical compound belonging to the labdane diterpene class, characterized by a 15,16-epoxy group, a hydroxyl group at the 12th position, and double bonds at the 8th, 13th, and 14th positions. It is found in certain plants and has been identified for its diverse biological activities, such as anti-inflammatory, anti-cancer, and anti-microbial properties. 15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene is currently under investigation for its potential therapeutic effects in treating a range of diseases and conditions.

Uses

Used in Pharmaceutical Industry:
15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene is used as a pharmaceutical agent for its anti-inflammatory properties, helping to reduce inflammation and alleviate symptoms associated with various inflammatory conditions.
Used in Oncology:
In the field of oncology, 15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene is utilized as an anti-cancer agent, targeting and inhibiting the growth of cancer cells. Its potential application in cancer treatment is being explored for various types of cancer.
Used in Microbiology:
15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene is employed as an anti-microbial agent, demonstrating effectiveness against certain microorganisms. This property makes it a candidate for use in treatments targeting microbial infections.
Used in Drug Development:
15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene is also used in drug development for its potential therapeutic effects. Researchers are investigating its mechanisms of action and efficacy in treating various diseases and conditions, with the aim of developing new drugs based on its chemical structure and biological activities.

Upstream product

• 66890-69-5 8α-hydroxy-15,16-epoxy-labda-13(16),14-dien-12-one 
• 190264-38-1 2-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)-N-methoxy-N-methylacetamide 
• 383159-58-8 1-(3-furyl)-2-[(1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-trans-naphthyl]methylketone 
• 434284-14-7 N-methoxy-N-methyl-2-((1S,4aS,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)acetamide 
• 3243-36-5 (1S,4aS,8aS)-1,2,3,4,4a,5,6,7,8,8a-decahydro-5,5,8a-trimethyl-2-methylene-1-naphthaleneacetaldehyde 
• 909794-71-4 (S)-1-(2-(triisopropylsilyloxy)furan-3-yl)-2-((1S,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)ethanol 
• 564-20-5 (3aR)-(+)-sclareolide 
• 1788090-69-6 3-((1S)-1-hydroxy-2-((1 S,8aS)-5,5,8a-trimethyl-2-methylenedecahydronaphthalen-1-yl)ethyl)-furan-2(5H)-one 
• 22037-28-1 3-bromofurane 

Downstream Products

• 1011287-43-6 (1-(furan-3-yl)-2-((1S,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl)ethoxy)triisopropylsilane 

Relevant articles and documents

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.

Facile access to labdane-type diterpenes: Synthesis of coronarin C, zerumin B, labda-8(17), 13(14)-dien-15,16-olide and derivatives from (+)-manool

A practical method for the synthesis of optically active labdane-type diterpenes from (+)-manool 8, is described. We prepared the natural labdane-type diterpene 5 via key intermediate peroxide 9 and coronarin C 1, compound 8 and zerumin B 6 via a furan photosensitised oxygenation reactions.

Synthesis of chinensines A-E

(Chemical Equation Presented) Short and efficient syntheses of coronarin E (4) and chinensines A-E (5-9) have been accomplished. The use of two different types of reaction of singlet oxygen (1O2) lies at the heart of the synthetic st