21747-46-6

Basic information

• Product Name: (+)-LEDENE
• Synonyms: 1,1,4,7-Tetramethyl-1a,2,3,5,6,7,7a,7b-octahydro-1H-cyclopropa[e]azulene;1H-Cycloprop[e]azulene, 1a,2,3,5,6,7,7a,7b-octahydro-1,1,4,7-tetramethyl-, [1aR-(1aalpha,7alpha,7abeta,7balpha)]-;Varidiflorene;Viridflorene;(1S,2R,3R,11R)-3,3,7,11-TETRAMETHYL-TRICYCLO[6.3.0.0(2.4)]UNDEC-7-ENE;(+)-LEDENE;[1aR-(1aalpha,7alpha,7abeta,7balpha)]-1a,2,3,5,6,7,7a,7b-octahydro-1,1,4,7-tetramethyl-1H-cycloprop[e]azulene;(+)-LEDENE 95+% MIXTURE OF ISOMERS
• CAS NO: 21747-46-6
• Molecular Formula: C₁₅H₂₄
• Molecular Weight: 204.35
• EINECS: 244-565-3
• Mol File: 21747-46-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 269°C
• Boiling Point: 268-270 °C(lit.)
• Flash Point: 101.3°C
• Appearance: /
• Density: 0.927 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.0164mmHg at 25°C
• Refractive Index: n20/D 1.504
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Sparingly), Ethanol (Slightly)
• BRN: 2554786
• CAS DataBase Reference: (+)-LEDENE(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-LEDENE(21747-46-6)
• EPA Substance Registry System: (+)-LEDENE(21747-46-6)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 21747-46-6(Hazardous Substances Data)

Usage

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: A carbotricyclic sesquiterpene obtained from several natural sources, including Australian Tea Tree oil (Melaleuca alternifolia.)

General Description

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

InChI:InChI=1/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h10,12-14H,5-8H2,1-4H3

Upstream product

• 489-41-8 ledol 
• 32543-79-6 (1S,3R)-2,2-dimethyl-3-(3-oxobutyl)cyclopropane-1-carbaldehyde 
• 4497-92-1 2-carene 
• 41437-00-7 (+)-bicyclogermacrene 
• 489-39-4 (+)-aromadendrene 
• 104472-69-7 pittosporanoside A₁ 
• 489-39-4 (+)-aromadendrene 

Downstream Products

• 34413-94-0 aromadendr-1⁽¹⁰⁾-en-9-one 

Relevant articles and documents

Biomimetic synthesis of (+)-ledene, (+)-viridiflorol, (-)-palustrol, (+)-spathulenol, and psiguadial A, C, and D via the platform terpene (+)-bicyclogermacrene

(+)-Bicyclogermacrene is a strained bicyclic and common sesquiterpene found in several essential oils. A short and good yielding synthesis of bicyclogermacrene proceeding in seven steps is reported. This terpene is used as key platform intermediate for a biomimetic access to several aromadendrene sesquiterpenoids, such as ledene, viridiflorol, palestrol, and spathulenol. Furthermore, bicyclogermacrene is shown to be the terpene component in the synthesis of the meroterpenoids psiguadial A, C, and D. Let nature be your guide! A concise synthesis of the terpene (+)-bicyclogermacrene enables its use as a platform for a fast access to a range of different terpenoids of the aromadendrene family and meroterpenoids of the psiguadial family (see scheme).

NEW TERPENOIDS OF THE ESSENTIAL OIL OF LEDUM PALUSTRE

The structures of two new natural compounds isolated from the essential oil of Ledum palustre L. have been established on the basis of their spectral characteristics as p-mentha-1,8(10)-diene 3,9-epoxide (lepaloks) and 3,10-epoxygermacr-4(14)-en-8-one (lepakson).The chemical structure of ledene as a sesquiterpene hydrocarbon has been determined by chemical correlation.

Katalytische Umwandlung von Sesquiterpenkohlenwasserstoffen an Alkalimetall/Aluminiumoxid-Kontakten

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