511-02-4

Basic information

• Product Name: Naphthalene,decahydro-1,1,
• Synonyms: Naphthalene,decahydro-1,1,;(4aS,8aα)-Decahydro-1,1,4aβ-trimethyl-6-methylene-5β-(3-methylene-4-pentenyl)naphthalene;Labda-8(17),13(16),14-triene;Sclaren;Sclarene
• CAS NO: 511-02-4
• Molecular Formula: C₂₀H₃₂
• Molecular Weight: 272.46808
• Mol File: 511-02-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 337.8°C at 760 mmHg
• Flash Point: 152.2°C
• Appearance: /
• Density: 0.88g/cm³
• Vapor Pressure: 0.000201mmHg at 25°C
• Refractive Index: 1.492
• CAS DataBase Reference: Naphthalene,decahydro-1,1,(CAS DataBase Reference)
• NIST Chemistry Reference: Naphthalene,decahydro-1,1,(511-02-4)
• EPA Substance Registry System: Naphthalene,decahydro-1,1,(511-02-4)

Safety Data

• Hazardous Substances Data: 511-02-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A diterpene that consists of a labdane skeleton with double bonds at C-8(17), C-13(16) and C-14.

InChI:InChI=1/C20H32/c1-7-15(2)9-11-17-16(3)10-12-18-19(4,5)13-8-14-20(17,18)6/h7,17-18H,1-3,8-14H2,4-6H3/t17-,18-,20+/m0/s1

Upstream product

• 596-85-0 epimanool 
• 596-85-0 manool 
• 596-85-0 (+)-manool 

Downstream Products

• 6138-92-7 labda-8(17),13E/Z-diene 
• 18457-49-3 1β-<2-<4,4,5,5-Tetracyan-cyclohexen-(1)-yl-(1)>-ethyl>-2-methylen-5,5,9β-trimethyl-trans-dekalin 

Relevant articles and documents

FOLIAGE DITERPENES OF DACRYDIUM INTERMEDIUM: IDENTIFICATION, VARIATION AND BIOSYNTHESIS

The major diterpenes in the foliage of Dacrydium intermedium have been identified as rimuene, ent-rosadiene, ent-beyerene, phyllocladene, ent-kaurene, sclarene and ent-sclarene. ent-Rosadiene and ent-sclarene have not been reported previously from natural sources.Considerable tree-to-tree variations are encountered and genetic control is proposed.Biosynthetic mechanism are put forward to explain the presence of diterpenes of both enantiomeric series.A lack of mono- and sesquiterpenes in both D. intermedium and D. fonkii, which ties in with Quinn's proposed revision of the Dacrydium genus, is also noted.Key Word Index - Dacrydium intermedium; D. fonkii; Podocarpaceae; infraspecific variation; biosynthesis; diterpenes; ent-rosadiene; ent-sclarene; co-occurrence of enantiomers; biochemical systematics; Lepidothamnus.

Development of synthetic routes to D,L-α-tocopherol (vitamin E) from biologically produced geranylgeraniol

The use of the biologically derived diterpene alcohol geranylgeraniol was explored as an alternative to petrochemical-based isophytol as a side-chain synthon for producing D,L-α-tocopherol. Two routes were studied, both of which begin with allylic epoxidation followed by olefin hydrogenation to give epoxyphytol. Epoxyphytol can be reduced with Red-Al to provide phytan-1,3-diol which upon acid-catalyzed condensation with trimethylhydroquinone gives vitamin E in fair yield. In a higher-yielding process, epoxyphytol was deoxygenated with methylrhenium trioxide/triphenylphosphine to generate a mixture of phytol and isophytol (> 90% yield from geranylgeraniol). This mixture can serve as a "plug-in" replacement for isophytol in the final step of the currently practiced vitamin E chemistry. The use of methylrhenium trioxide to catalyse dehydration of vinyl dialkyl carbinols to 1,3-dienes was also demonstrated.