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Terpenes

 Terpenes are a large family of natural products and are known to be the primary constituents of essential oils. They are biosynthesized via the mevalonate pathway. The basic structure is derived from five-carbon isoprene units1,2) which are linked together in a head-to-tail fashion to form linear chains or rings. They can be classified on the basis of the length of the carbon chains as illustrated below.

Table 1. Classification of Terpenes and Examples

Name Number of Carbons Examples
Hemiterpenes 5 Isoprene
Monoterpenes 10 Menthol, Geraniol: Flavors, Food Additives
Sesquiterpenes 15 Artemisinin: Antimalarial Drug
α-Bisaborol: Flavor, Cosmetic Ingredients
Diterpenes 20 Paclitaxel: Antitumor Agent, Gibberellins: Plant Hormones
Triterpenes 30 Lanosterol: Precursor of Steroid Biosynthesis
 Terpenes are widespread in nature existing in marine organisms as well as in plants. Some terpenes show characteristic bioactivity such as antitumor activities, and their modes of action is currently under investigation. Since terpenes are mainly found in plants, they are frequently used as markers in plant metabolome analyses.

■Nomenclature
According to the IUPAC Nomenclature Appendix, 42 parent skeletons are shown.3) Practically, other common names are also used frequently. For further trivial names, please refer to References.2,4)

■Solubility
In general, most of the terpenes are insoluble in water but soluble in ethanol, chloroform and diethyl ether. They can be added to the buffer solution as a dimethyl sulfoxide solution to examine their activity in living organisms. Please take caution that the solution becomes suspended as the concentration level of the dissolved substance increases. It is recommended to define the optimal concentration level and volume of addition in advance. Glycosides of terpenes are more water-soluble than their aglycones.

■Stability
In general, monoterpenes are relatively stable. However, oily sesquiterpenes and diterpenes are less stable bearing more oxygen fuctional groups rendering them unsuitable for storage over longer periods. However, most of the triterpenes are solid and show good stability.

■Detection
Since some terpenes do not have chromophore unit, UV detection by normal-phase HPLC is difficult. As a result, RI (refractive index) detector can be used instead. Normal-phase TLC is also frequently used to visualize terpenes by spraying them with phosphomolybdic acid solution or cerium sulfate solution followed by heating.

■Some Tips
▪ Monoterpenes and some sesquiterpenes form azeotropic mixtures with the traces of water present in the sample, leading to a considerable loss during distillation. It is therefore recommended that these terpenes should be properly dried prior to their use using the following procedure:
(1) dissolution of the sample in an appropriate organic solvent (2) drying it over anhydrous sodium or magnesium sulfate and (3) removal of the solvent in vacuo.
▪ In NMR measurement, using two different solvents separately, deuteriochloroform (CDCl3) and benzene-d6 (C6D6), may change the signal patterns to facilitate interpretation of the spectrum (mainly for proton). In addition, some hidden signals might also appear owing to the variation in the residual water signal positions.
▪ During storage over longer periods, CDCl3 might partially decompose to form phosgene which can damage your precious sample. Therefore care should be taken especially while using CDCl3 with high deuterium ratio (no less than 99.95%D). The sample should not be stored in the NMR tube as a solution after its analysis but recovered from the tube and the solvent should be evaporated completely to prevent its decomposition.

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B0525
Borneol (contains ca. 20% Isoborneol)
B0526
Bornyl Acetate (contains ca. 20% Isobornyl Acetate)
B0567
(+)-3-Bromocamphor
B1012
(-)-Borneol
B1125
(+)-3-Bromocamphor-8-sulfonic Acid Ammonium Salt
B4412
(-)-3-Bromocamphor-8-sulfonic Acid Ammonium Salt
C0009
(±)-Camphene (contains ca. 20% Tricyclene)
C0010
(+)-Camphor
C0011
(±)-Camphor
C0013
(1R)-Camphor Oxime
C0014
(±)-Camphorquinone
C0015
(+)-10-Camphorsulfonic Acid
C0016
(±)-10-Camphorsulfonic Acid
C0017
Sodium (±)-10-Camphorsulfonate
C0047
(+)-3-Carene
C0542
1,8-Cineole
C0934
1,8-Cineole
C0972
(-)-10-Camphorsulfonic Acid
C0998
(+)-10-Camphorsulfonyl Chloride
C1021
(-)-Camphanic Acid
C1022
(-)-Camphanic Chloride
C1251
(-)-Camphor
C1308
(-)-10-Camphorsulfonyl Chloride
C1324
(+)-10,2-Camphorsultam
C1325
(-)-10,2-Camphorsultam
C1326
(2R,8aS)-(+)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
C1327
(2S,8aR)-(-)-(Camphorylsulfonyl)oxaziridine [Asymmetric Oxidizing Reagent]
C1391
(+)-10-Camphorsulfonimine
C1393
(-)-10-Camphorsulfonimine
C1482
(1R)-(-)-Camphorquinone
C1660
(1S)-(+)-Camphorquinone
C1661
anti-(1R)-(+)-Camphorquinone 3-Oxime
D2715
(+)-3,9-Dibromocamphor
F0163
(+)-Fenchone
F0164
(-)-Fenchone
F1187
Fraxinellone
G0385
Geniposide
G0458
Genipin
H0862
(1R,2R,5R)-(+)-2-Hydroxy-3-pinanone
H0863
(1S,2S,5S)-(-)-2-Hydroxy-3-pinanone
I0275
(±)-Isoborneol
I0306
Isobornyl Acetate
I0617
Isobornyl Methacrylate (stabilized with MEHQ)
I0638
Isobornyl Acrylate (stabilized with MEHQ)
K0028
(S)-(+)-Ketopinic Acid
M1070
(1S)-(-)-10-Mercaptoisoborneol
M1341
(1S)-(-)-10-Mercaptoborneol
P0440
(1S)-(-)-α-Pinene
P0441
(-)-β-Pinene
P1099
(1R)-(+)-α-Pinene
P1362
α-Pinene Oxide
P1876
Paeoniflorin
P1934
(1S,2S,3R,5S)-(+)-2,3-Pinanediol
S0897
Swertiamarin
T0989
Thujone (α- and β- mixture)
T1863
(1R)-(-)-Thiocamphor
T2578
(1R,4R,5R)-4,7,7-Trimethyl-6-thiabicyclo[3.2.1]octane
T2579
(1S,4S,5S)-4,7,7-Trimethyl-6-thiabicyclo[3.2.1]octane
V0072
(-)-Verbenone

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References

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