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

General Description

15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene is a natural chemical compound found in certain plants that belongs to the labdane diterpene class. It is named for its structure, which includes a 15,16-epoxy group, a hydroxyl group at the 12th position, and a double bond at the 8th, 13th, and 14th positions. 15,16-Epoxy-12S-hydroxylabda-8(17),13(16),14-triene has been found to possess various biological activities, including anti-inflammatory, anti-cancer, and anti-microbial properties. It is being studied for its potential therapeutic effects in the treatment of various diseases and conditions.

Upstream product

• 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 
• 190264-38-1 2-((1R,2R,4aS,8aS)-2-hydroxy-2,5,5,8a-tetramethyldecahydronaphthalen-1-yl)-N-methoxy-N-methylacetamide 
• 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 
• 66890-69-5 8α-hydroxy-15,16-epoxy-labda-13(16),14-dien-12-one 
• 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 
• 564-20-5 (3aR)-(+)-sclareolide 

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