83324-51-0

Basic information

• Product Name: 8(17),13-Labdadien-15,16-olide
• Synonyms: 8(17),13-Labdadien-15,16-olide
• CAS NO: 83324-51-0
• Molecular Formula: C20H30O2
• Molecular Weight: 302
• Mol File: 83324-51-0.mol
• Article Data: 5

Chemical Properties

• Melting Point: 76-78 °C(Solv: hexane (110-54-3))
• Boiling Point: 423.3±14.0 °C(Predicted)
• Appearance: /
• Density: 1.02±0.1 g/cm3(Predicted)
• CAS DataBase Reference: 8(17),13-Labdadien-15,16-olide(CAS DataBase Reference)
• NIST Chemistry Reference: 8(17),13-Labdadien-15,16-olide(83324-51-0)
• EPA Substance Registry System: 8(17),13-Labdadien-15,16-olide(83324-51-0)

Safety Data

• Hazardous Substances Data: 83324-51-0(Hazardous Substances Data)

Usage

General Description

8(17),13-Labdadien-15,16-olide is a natural chemical compound found in various plants and is known for its potent biological activities. It has been identified as a sesquiterpene lactone, and is believed to possess anti-inflammatory, anti-cancer, and anti-microbial properties. Research suggests that 8(17),13-Labdadien-15,16-olide may have potential as a drug candidate for the treatment of various diseases. Its molecular structure contains a unique arrangement of atoms, which may contribute to its diverse pharmacological activities. Further study is needed to fully understand the potential benefits and risks associated with the use of this compound in medicine and other applications.

Upstream product

• 176050-48-9 16-oxo-8⁽¹⁷⁾,12(E)-labdadien-15-oic acid 
• 104263-85-6 (E)-labda-8⁽²⁰⁾,12-diene-15,16-dial 
• 61597-53-3 4-[2-((1S,4aS,8aS)-5,5,8a-Trimethyl-2-methylene-decahydro-naphthalen-1-yl)-ethyl]-3,6-dihydro-[1,2]dioxine 
• 73818-55-0 Bestmann ylide 
• 73609-56-0 (+)-(Z)-labda-8-⁽¹⁷⁾,13-diene-15,16-diol 
• 16633-27-5 (E)-3-Methyl-5-((1S,4aS)-5,5,8a-trimethyl-2-methylene-decahydro-naphthalen-1-yl)-pent-2-enal 

Relevant articles and documents

Synthesis and antimalarial activities of optically active labdane-type diterpenes

An efficient 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 synthetic hydroxybutenolides 6 and 7 via a furan photosensitised oxygenation reaction of labdafuran (14). Compounds 5, 6, 7 and 9 were evaluated as inhibitors of the β-haematin formation and globin proteolysis, and then were assayed in a malarial murine model. Compound 9 was the most promising compound, showing a positive correlation between in vitro and in vivo activities.

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 LABDA-8(17),13(14)-DIENE-15,16-OLIDE AND 15,16-EPOXY-LABDA-8(17),13(16)-14-TRIENE AND THEIR REARRANGEMENT TO CLERODANE DERIVATIVES

The title compounds 1b and 1c were synthesized from manool.On treatment with either trifluoroacetic acid or formic acid 1b provided in nearly 100percent yield 4a with a rearranged labdane skeleton.With sulfuric acid, however, 1b gave solely Δ8,9-isomer 5.Reduction of 4a with lithium diisobutylaluminium hydride afforded 4b.On treatment with sulfuric acid 4a reverted to 5.Rearrangement of the epoxide 6 with boron trifluoride-etherate led to a complex product mixture from wich no pure substance was obtained.