Caryophylene
Caryophyllene is a sesquiterpinoid constituent of many essential oils, in particular, clove oil and in the stems and flowers of Syzyglum aromaticum. There are two forms caryophyllene a caryophyllene and B caryophyllene and they usually occur together with isocaryophyllene. Caryophyllene is a hydrocarbon with a molecular weight of 204.36 and elemental analysis shows it contains 88.16% carbon and 11.84% hydrogen. Caryophyllene is present in many essential oils, for example lime oil, and is frequently used in the blending of synthetic oils and fragrances. The analysis of lime oil, including the separation and estimation of the caryophyllene content, can easily be carried out by gas chromatography. A very effective stationary phase for this purpose is poly (5%diphenyl-95%-dimethylsiloxane). Although the diphenyl group will contribute some induced polaizability and be capable of interacting with polar and semi-polar solutes, it is largely a dispersive stationary phase. In addition, as caryophyllene is a hydrocarbon, the only retentive forces that will be active on this solute will be dispersive. The introduction of the diphenyl groups into the stationary phase increases its temperature stability An example of a suitable capillary column would be 30m long, 250 micron ID carrying a film of stationary phase 0.25 micron thick. At a linear mobile phase velocity of 25 cm/sec and temperature programmed form 155C to 200C the components of lime oil ranging from pinene to bisabolen can be eluted in about 30 minutes.
Author: RPW Scott
Book:Gas Chromatography - Tandem Techniques
Section:GC-Tandem Introduction
mixtures that fired the imagination of chemists world-wide. For the first time the complex nature of these important materials could be displayed both quantitatively and qualitatively. An example of the separation of an essential oil using modern GC equipment is shown in figure 1 .
1. a-Pinene 7. gÐTerpinene 13. Geraniol
2. Camphene 8. Terpinolene 14. Neryl Acetate
3. b-Pinene 9. Linalool 15. Geranyl Acetate
4. Myrcene 10. Terpinene-4-ol 16. Caryophyllene
5. p-Cymene 11. a-Terpineol 17. trans-a-Bergamotene
6. Limonene 12. Neral 18. b-Bisabolen
Courtesy of Supelco, Inc.
Figure 7 A Chromatogram of Lime Oil
GC-Tandem Introduction
Author: RPW Scott
Book:Principles and Practice of Chromatography
Section:Principles Applications Gas-Chromatography Essential-Oils
. The column
was 30 m long, 250 mm I.D. carrying a
film 0.25 mm thick of stationary phase.
Helium was used as the carrier gas at a linear velocity of 25 cm/sec(set at
155˚C).
1. a–Pinene
7. g–Terpinene
13. Geraniol
2. Camphene
8. Terpinolene
14. Neryl Acetate
3. b–Pinene
9. Linalool
15. Geranyl Acetate
4. Myrcene
10. Terpinene–4–ol
16. Caryophyllene
5. p–Cymene
11. a–Terpineol
17.trans–a–Bergamotene
6. Limonene
12. Neral
18. b–Bisabolen
Courtesy of Supelco Inc.
Figure 39 A Chromatogram of
Lime Oil
The column was
held isothermally for 8 min. at 75˚C and then programmed up to 200˚C
at 4˚c/min. and finally held at 200˚C for 4 min. The sample volume
was 0.5 ml which was split at 100:1
ratio
Principles Applications Gas-Chromatography Essential-Oils
Author: RPW Scott
Book:Gas Chromatography
Section:YES Applications Lime-Oil
polarizability capability to interact with polar solutes. As a
consequence substances are eluted roughly in order of their boiling points
(excepting very polar solutes).
1. a–Pinene
7. g–Terpinene
13. Geraniol
2. Camphene
8. Terpinolene
14. Neryl Acetate
3. b–Pinene
9. Linalool
15. Geranyl Acetate
4. Myrcene
10. Terpinene–4–ol
16. Caryophyllene
5. p–Cymene
11. a–Terpineol
17. trans–a–Bergamotene
6. Limonene
12. Neral
18. b–Bisabolen
Courtesy of Supelco Inc.
Figure 43 A Chromatogram of
Lime Oil
The
introduction of the diphenyl groups contributes more to phase temperature
stability than it does to solute selectivity. The column was 30 m long, 250 mm I.D. carrying a film 0.25 mm thick of stationary phase.
YES Applications Lime-Oil
