Santalene

The Santalene are a group of natural substances . Structurally, they belong to the tricyclic sesquiterpenes and thus to the hydrocarbons . There are three stereoisomers that occur in East Indian sandalwood oil .

Representative

Santalene

Surname

(-) - α-Santals

(-) - β-santals

(+) - epi -β santals

Structural formula

other names

(-) - 1,7-Dimethyl-7- (4-methyl-3-pentenyl) -tricyclo [2.2.1.0 ^2,6 ] heptane
6,7-dimethyl-7- (4-methylpent-3-enyl) -2,3,4,5-tetrahydro-1H-tricyclo [2.2.1.0 ^2,6 ] heptane

(1 R , 3 R , 4 S ) -3-methyl-2-methylidene-3- (4-methylpent-3-enyl) bicyclo [2.2.1] heptane

(3 S ) -3-methyl-2-methylidene-3- (4-methylpent-3-enyl) bicyclo [2.2.1] heptane

CAS number

512-61-8

511-59-1

25532-78-9

PubChem

C ₁₅ H ₂₄

204.35 g mol ⁻¹

liquid

Brief description

Oils

boiling point

252 ° C (100.1 kPa)

125-127 ° C (1.2 kPa)

94–115 ° C (3–7 kPa)

GHS
labeling

no classification available

H and P phrases

see above

Occurrence

Sandalwood tree

All three isomers occur in addition to α- santalol in the Indian sandalwood oil from Santalum album ; the (+) - epi -β-Santalen, however, only in traces.

(-) - α-Santalen can also be found in traces in lavender oil , as well as in butterbur ( Petasites hybridus ).

properties

The smell of α-santals is described as weak, whereas β-santals have a cedar note . The β-santalenes have a bicyclo [2.2.1] heptane structure, while the α-derivatives are tricyclic in nature.

history

Santalen is the first sesquiterpene from which a correct structural formula could be determined, this was done in 1910 by Friedrich Wilhelm Semmler .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g Entry on Santalene. In: Römpp Online . Georg Thieme Verlag, accessed on January 7, 2017.
^ FW Semmler: On the knowledge of the components of essential oils. (Constitution of the α-Santalol and α-Santalen series: The constitution of the sesquiterpene alcohols and sesquiterpenes.). In: Reports of the German Chemical Society. 43, 1910, p. 1893, doi: 10.1002 / cber.191004302121 .

[Roempp-1] ↑ ^a ^b ^c ^d ^e ^f ^g Entry on Santalene. In: Römpp Online . Georg Thieme Verlag, accessed on January 7, 2017.

[2] FW Semmler: On the knowledge of the components of essential oils. (Constitution of the α-Santalol and α-Santalen series: The constitution of the sesquiterpene alcohols and sesquiterpenes.). In: Reports of the German Chemical Society. 43, 1910, p. 1893, doi: 10.1002 / cber.191004302121 .