(+)-Ledene Chemical Properties

Melting point:

269°C

Boiling point:

268-270 °C (lit.)

Density 

0.927 g/mL at 20 °C (lit.)

refractive index 

n20/D 1.504

storage temp. 

Refrigerator

solubility 

Chloroform (Sparingly), Ethanol (Slightly)

form 

Oil

color 

Colourless

optical activity

[α]20/D +68±2°, c = 10% in ethanol

BRN 

2554786

LogP

6.447 (est)

Safety Information

Safety Statements 

23-24/25

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

(+)-Ledene Usage And Synthesis

Description

(+)-Ledene, also called leden or viridiflorene, is an organic compound that belongs to the group of 5, 10-cycloaromadendrane sesquiterpenoids. These compounds are derived from the aromadendrane skeleton through a cyclization reaction between carbon atoms 5 and 10. (+)-Ledene is mainly found in saliva and is considered to have low solubility in water and a relatively neutral nature. In cellular environments, (+)-ledene is predominantly present in the cell membrane (predicted based on logP) and cytoplasm.

Uses

(+)-Ledene is an essential oil that is synthesized by viridiflorene synthase. It has been studied as an antioxidant, antimicrobial, antibiofilm and to treat various cancers.

Definition

ChEBI: Viridiflorene is a carbotricyclic sesquiterpene obtained from several natural sources, including Australian Tea Tree oil (Melaleuca alternifolia.) It is a sesquiterpene and a carbotricyclic compound.

General Description

(+)-Ledene is a naturally occurring sesquiterpene that can be prepared from (+)-aromadendrene via isomerization.

References

[1] DUC N. TRAN   Prof.??Dr. N C. Biomimetic Synthesis of (+)-Ledene, (+)-Viridiflorol, (?)-Palustrol, (+)-Spathulenol, and Psiguadial A, C, and D via the Platform Terpene (+)-Bicyclogermacrene[J]. Chemistry - A European Journal, 2014. DOI:10.1002/chem.201403082.
[2] S. L. GWALTNEY   K. J S  S T Sakata. Bridged to Fused Ring Interchange. Methodology for the Construction of Fused Cycloheptanes and Cyclooctanes. Total Syntheses of Ledol, Ledene, and Compressanolide[J]. The Journal of Organic Chemistry, 1996. DOI:10.1021/jo961005a.

(+)-Ledene(21747-46-6)Related Product Information

• CYCLOOCTENE
• (+)-Ledene
• CIS-1,2-DIMETHYLCYCLOPROPANE
• ETHYLIDENECYCLOPENTANE
• CYCLOHEPTENE
• 3-METHYLCYCLOOCTENE
• 1-METHYL-1-CYCLOHEPTENE
• 1-METHYL-1-CYCLOOCTENE
• METHYLENECYCLOPENTANE
• (1,2-DIMETHYLPROPYL)CYCLOPROPANE
• TRANS-1,2-DIMETHYLCYCLOPROPANE
• 2,3-DIMETHYL-2-OCTENE
• CIS-1-ETHYL-2-METHYLCYCLOPROPANE
• CIS-1,2-DIETHYLCYCLOPROPANE
• 2,3-DIMETHYL-2-HEPTENE
• (1-METHYLBUTYL)CYCLOPROPANE
• SEC-BUTYLCYCLOPROPANE