Terpenes

Terpenes is the generic term summarizing all kinds of isoprene polymers and their derivatives with its general formula of (C5H8) n. Terpene is a class of compound that is ubiquitous in the plant kingdom, but exist in very few amount in the animal kingdom. Except in the form of terpene hydrocarbons, there are a large number of terpenes forming various kinds of oxygenated derivatives including alcohols, aldehydes, ketones, carboxylic acids, esters and glycoside forms. Secondly there are also nitrogen-containing derivatives as well as a minority of sulfur-containing derivatives presented. Based on the number of the isoprene units contained inside the molecule, the terpenes can be divided into: monoterpene, sesquiterpenoid, diterpene, sesquiterpene, triterpenoids, tetraterpene and polyterpene.

For some compound which originated from the synthesis of isoprene, but has the number of carbon atoms in the molecule be not an integer multiple of 5, they are called terpenoid. In the life activities, terpenoids compound, especially inside the plants, have important functions, for example gibberellin, abscisic acid and insect juvenile hormone are important hormones, carotenoids and chlorophyll are important photosynthetic pigments; plastoquinone and quinone are respectively important electronic chain delivery body in photosynthesis and respiration chain; sterols are the component of the biological membrane.

Monoterpene and sesquiterpene are the major component of volatile oil. Diterpene is the major substance forming the resin; triterpenoid is an important material forming plant saponins and resins, tetraterpene mainly include some fat-soluble pigments widely distributed in the plants. In nature, terpenoids is widely distributed, some of which have physiological activity. For example, ascaridole and santonin have roundworm expelling effect; artemisinin has antimalarial effect while andrographolidume has antibacterial effect.

The following describes some of the chemical reactions associated with terpenes. This is significant for determination of the chemical structure of terpene component.

(1) Oxidation reaction
Different oxidants, in different situations, can oxidize the different groups contained in terpene component to produce different products. For example, chromic acid can oxidize the carbon methyl group and gem-dimethyl carbon to produce acetic acid; the oxidation reaction of ozone is a valuable double bond cleavage reaction and can determine the position of double bond in the structure of the terpene composition. Lead tetraacetate is also oxidation agents of double-bond and has been widely used in chemical research of the terpene ingredients.

(2) The dehydrogenation
Dehydrogenation reaction can be considered as a kind of oxidation reactions and is a kind of valuable reaction for the study the chemical structure of terpenes particularly cyclic terpene. It refers to that the terpene component is heated (200 ℃ ~ 300 ℃) together with sulfur or selenium under an inert atmosphere, the carbon skeleton of the cyclic terpene is dehydrogenated into aromatic derivatives with sometimes the ring being cleaved and sometimes cyclization occurring simultaneously.

(3) Addition reaction
The double bonds in the terpene components can react with hydrogen halide acids such as hydroiodic acid or hydrogen chloride in glacial acetic acid solution to generate crystalline-shaped addition product. It can also absorb bromine (diethyl ether or glacial acetic acid - ethanol solution) to generate bromide with certain physicochemical properties. If mixing the glacial acetic acid and sodium nitrite for shaking, nitrous oxide or pseudo-nitrous oxide will be generate and will exhibit visible special colors.
If the unsaturated terpene component was added with amyl nitrite and concentrated hydrochloric acid for mixing with shaking and keep it cool, then add a small amount of ethanol or glacial acetic acid, there will be chlorinated nitroso derivative of terpenes generated with special colors as well. Such nitroso derivatives (including nitrous oxides and chlorinated nitroso derivative) mostly exhibit blue or blue-green color. They are easily polymerized to form a colorless di-polymer, but when the di-polymer is heated to a molten state or when made into a solution, it can also be converted into a blue or blue-green single-molecule compound.
Nitroso chlorinated derivatives can condense with primary or secondary amines (commonly piperidine) to generate nitroso amines with most of them having complete crystal shape and  certain physical and chemical constants available for the identification of unsaturated terpene components. If the terpene component molecules contain conjugated double bonds, then it will form crystalline addition product with maleic anhydride through Diels-Alder reaction which can be used to prove the presence of conjugated double bonds.

(4) Wagner-Meerweein rearrangement;
Terpene molecules, sometimes through the effect of agents (such as acid, etc.), the carbon skeleton can be changed or the functional groups in the molecule can be transferred in the molecule. Especially during the elimination reaction, addition reaction or a nucleophilic substitution reaction of bicyclic terpene compound, there is often Wagner-Meerweein rearrangement happening.

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Structure Chemical Name CAS MF
Coronarin E Coronarin E 117591-81-8 C20H28O
ISOPIMARIC ACID ISOPIMARIC ACID 5835-26-7 C20H30O2
6-ACETYL-7-DEACETYLFORSKOLIN 6-ACETYL-7-DEACETYLFORSKOLIN 64657-21-2 C22H34O7
FRIEDELAN-3ALPHA-OL FRIEDELAN-3ALPHA-OL 5085-72-3 C30H52O
Gaderiol F Gaderiol F 114567-47-4 C30H46O3
Przewalskin Przewalskin 119400-87-2 C18H24O2
ent-16beta,17-Dihydroxy-19-kauraic acid ent-16beta,17-Dihydroxy-19-kauraic acid 3301-61-9 C20H32O4
Hederagonic acid Hederagonic acid 466-01-3 C30H46O4
PHYTOLACCOSIDEB PHYTOLACCOSIDEB 60820-94-2 C36H56O11
Ursolic acid acetate Ursolic acid acetate 7372-30-7 C32H50O4
1-HYDROXYBACCATIN I 1-HYDROXYBACCATIN I 30244-37-2 C32H44O14
kaurenoic acid kaurenoic acid 6730-83-2 C20H30O2
2α,3β-Dihydroxylup-20(29)-en-28-oic acid 2α,3β-Dihydroxylup-20(29)-en-28-oic acid 19533-92-7 C30H48O4
Coccinic acid Coccinic acid 107783-45-9 C30H46O3
MudanpiosideC MudanpiosideC 172760-03-1 C30H32O13
1-Dehydroxy-23-deoxojessic acid 1-Dehydroxy-23-deoxojessic acid 149252-87-9 C31H50O3
2,2,5,5-Tetramethylcyclohexane-1,4-dione 2,2,5,5-Tetramethylcyclohexane-1,4-dione 86838-54-2 C10H16O2
7-Hydroxydarutigel 7-Hydroxydarutigel 1188281-99-3 C20H34O4
C(14a)-Homo-27-norgammacer-14-ene-3β,21β-diol 3-acetate C(14a)-Homo-27-norgammacer-14-ene-3β,21β-diol 3-acetate 1260-05-5 C32H52O3
(S)-2,3-Bis(hydroxymethyl)-1-(2-hydroxyethyl)-1-cyclopentene (S)-2,3-Bis(hydroxymethyl)-1-(2-hydroxyethyl)-1-cyclopentene 126594-64-7 C9H16O3
(2E,6E)-8-Hydroxy-2,6-dimethyl-2,6-octadienoic acid (2E,6E)-8-Hydroxy-2,6-dimethyl-2,6-octadienoic acid 26187-80-4 C10H16O3
Isosalvipuberulin Isosalvipuberulin 115321-32-9 C20H14O5
TRIPTOQUINONEB TRIPTOQUINONEB 142937-50-6 C20H26O4
12-Acetoxyabietic acid 12-Acetoxyabietic acid 83905-81-1 C22H32O4
12-Ursene-3,16,22-triol 12-Ursene-3,16,22-triol 1242085-06-8 C30H50O3
15,16-Di-O-acetyldarutoside 15,16-Di-O-acetyldarutoside 1188282-02-1 C30H48O10
15-Isopimarene-8,18-diol 15-Isopimarene-8,18-diol 73002-86-5 C20H34O2
19-[(beta-D-glucopyrasyl)oxy]-
19-oxo-ent-labda-8(17),13-dien-16,15-olide 19-[(beta-D-glucopyrasyl)oxy]- 19-oxo-ent-labda-8(17),13-dien-16,15-olide 919120-78-8 C26H38O9
2,3,24-Trihydroxyolean-12-en-28-oic acid 2,3,24-Trihydroxyolean-12-en-28-oic acid 150821-16-2 C30H48O5
27-p-Coumaroyloxyursolic acid 27-p-Coumaroyloxyursolic acid 73584-67-5 C39H54O6
3-Acetoxy-8(17),13E-labdadien-15-oic acid 3-Acetoxy-8(17),13E-labdadien-15-oic acid 63399-37-1 C22H34O4
8(14),15-Isopimaradiene-3,18-diol 8(14),15-Isopimaradiene-3,18-diol 59219-64-6 C20H32O2
Biondinin C Biondinin C 55511-08-5 C19H24O3
Cabraleadiol Cabraleadiol 67253-01-4 C30H52O3
Ceathic acid acetate Ceathic acid acetate 119533-63-0 C32H48O6
Chinensine B Chinensine B 849245-34-7 C20H28O3
Coronalolide Coronalolide 268214-51-3 C30H42O5
Dammaradienyl acetate Dammaradienyl acetate 52914-31-5 C31H50O2
ent-11,16-Epoxy-15-hydroxykauran-19-oic acid ent-11,16-Epoxy-15-hydroxykauran-19-oic acid 77658-46-9 C20H30O4
Epifriedelal acetate Epifriedelal acetate 2259-07-6 C32H54O2
Forskolin J Forskolin J 81873-08-7 C24H36O8
Lophanthoidin F Lophanthoidin F 120462-46-6 C24H34O7
Methyl lycernuate A Methyl lycernuate A 56218-46-3 C31H50O4
Piscidil A Piscidil A 100198-09-2 C30H50O4
p-Menthane-1,3,8-triol p-Menthane-1,3,8-triol 155348-06-4 C10H20O3
Quivin Quivin 107870-05-3 C36H56O9
Sculponeatin N Sculponeatin N 1169805-98-4 C25H40O4
Semialactone Semialactone 366450-46-6 C30H44O4
Squalene-2,3-diol Squalene-2,3-diol 14031-37-9 C30H52O2
Yunnancoronarin A Yunnancoronarin A 162762-93-8 C20H28O2
2,5,9,14-Tetraacetoxy-3-benzoyloxy-8,15-dihydroxy-7-isobutyroyloxyjatropha-6(17),11E-diene 2,5,9,14-Tetraacetoxy-3-benzoyloxy-8,15-dihydroxy-7-isobutyroyloxyjatropha-6(17),11E-diene 210108-88-6 C39H52O14
23-HydroxyMangiferonic acid 23-HydroxyMangiferonic acid 232266-08-9 C30H46O4
28-Hydroxy-3-oxoolean-12-en-29-oic acid 28-Hydroxy-3-oxoolean-12-en-29-oic acid 381691-22-1 C30H46O4
Labd-13-ene-8,15-diol Labd-13-ene-8,15-diol 10267-31-9 C20H36O2
Glochidone Glochidone 6610-55-5 C30H46O
(24Z)-3,4-Secolanosta-4(28),9(11),24-triene-3,26-dioic acid (24Z)-3,4-Secolanosta-4(28),9(11),24-triene-3,26-dioic acid 62393-88-8 C30H46O4
(13S,14S,17S)-3,6-Dioxo-16β-hydroxylanosta-7,24-diene-21-oic acid γ-lactone (13S,14S,17S)-3,6-Dioxo-16β-hydroxylanosta-7,24-diene-21-oic acid γ-lactone 64929-59-5 C30H42O4
Alstonic acid B Alstonic acid B 1159579-45-9 C30H46O3
Coronalolic acid Coronalolic acid 268214-52-4 C30H46O4
Daturabietatriene Daturabietatriene 65894-41-9 C20H30O2
Dihydroajugapitin Dihydroajugapitin 87480-84-0 C29H44O10
ent-6,9-Dihydroxy-15-oxo-16-kauren-19-oic acid ent-6,9-Dihydroxy-15-oxo-16-kauren-19-oic acid 81264-00-8 C20H28O5
Isotschimgin Isotschimgin 62356-47-2 C17H22O3
Liangshanin A Liangshanin A 122717-54-8 C20H26O4
Masticadielic acid Masticadielic acid 472-30-0 C30H48O3
Methylpseudolarate B Methylpseudolarate B 82508-34-7 C24H30O8
Momethyl kolavate Momethyl kolavate 24513-41-5 C21H32O4
Ohchinin acetate Ohchinin acetate 67023-81-8 C38H44O9
Simiarene Simiarene 2318-78-7 C30H48O
Tetrahydroxysqualene Tetrahydroxysqualene 1043629-23-7 C30H50O4
15,16-Dihydro-15-Methoxy-16-oxohardwickiic acid 15,16-Dihydro-15-Methoxy-16-oxohardwickiic acid 115783-35-2 C21H30O5
3,27-Dihydroxy-20(29)-lupen-28-oic acid Methyl ester 3,27-Dihydroxy-20(29)-lupen-28-oic acid Methyl ester 263844-79-7 C31H50O4
14-Deoxy-11,12-didehydroandrographiside 14-Deoxy-11,12-didehydroandrographiside 141973-41-3 C26H38O9
3,10-Dihydroxy-5,11-dielMenthadiene-4,9-dione 3,10-Dihydroxy-5,11-dielMenthadiene-4,9-dione 106623-23-8 C20H28O4
Quinovic acid 3-O-alpha-L-rhaMnopyranoside Quinovic acid 3-O-alpha-L-rhaMnopyranoside 104055-76-7 C36H56O9
ZEORINE ZEORINE 22570-53-2 C30H52O2
Trichokaurin Trichokaurin 23811-50-9 C24H34O7
Forrestin A Forrestin A 152175-76-3 C30H42O11
Fupenzic acid Fupenzic acid 119725-20-1 C30H44O5
Myriceric acid C Myriceric acid C 162059-94-1 C48H60O10
Pepluanin A Pepluanin A 670257-89-3 C43H51NO15
Rubifolic acid Rubifolic acid 80489-65-2 C30H48O4
Scutebarbatine B Scutebarbatine B 905929-95-5 C33H35NO7
Simiarel acetate Simiarel acetate 4965-99-5 C32H52O2
Villosin C Villosin C 160927-81-1 C20H24O6
3,6,19-Trihydroxy-23-oxo-12-ursen-28-oic acid 3,6,19-Trihydroxy-23-oxo-12-ursen-28-oic acid 131984-82-2 C30H46O6
13-Epijhanol 13-Epijhanol 133005-15-9 C20H34O2
2',3'-Dehydrosalannol 2',3'-Dehydrosalannol 97411-50-2 C32H42O8
Cabralealactone Cabralealactone 19865-87-3 C27H42O3
Dulcioic acid Dulcioic acid 78516-69-5 C30H48O3
Quinovic acid 3-O-(3',4'-O-isopropylidene)-beta-D-fucopyranoside Quinovic acid 3-O-(3',4'-O-isopropylidene)-beta-D-fucopyranoside 182132-59-8 C39H60O9
Triptocallic acid D Triptocallic acid D 201534-09-0 C30H48O4
19-hydroxybaccatin III 19-hydroxybaccatin III 78432-78-7 C31H38O12
cycloleucalenol cycloleucalenol 469-39-6 C30H50O
(20R,24S)-20,24-Epoxy-25-hydroxydammaran-3-one (20R,24S)-20,24-Epoxy-25-hydroxydammaran-3-one 22549-21-9 C30H50O3
(4S)-C(14a)-Homo-27-norgammacer-14-ene-3α,21β,24-triol (4S)-C(14a)-Homo-27-norgammacer-14-ene-3α,21β,24-triol 13956-51-9 C30H50O3
20-Hydroxy-4,8,14-trimethyl-4-methylene-18-nor-3,4-seco-5β-cholane-3,24-dioic acid γ-lactone 20-Hydroxy-4,8,14-trimethyl-4-methylene-18-nor-3,4-seco-5β-cholane-3,24-dioic acid γ-lactone 2202-01-9 C27H42O4
(4R)-3β,21β-Dihydroxy-C(14a)-homo-27-norgammacer-14-en-23-oic acid (4R)-3β,21β-Dihydroxy-C(14a)-homo-27-norgammacer-14-en-23-oic acid 53755-77-4 C30H48O4
1,4-Epoxy-p-menthane-2,3-diol 1,4-Epoxy-p-menthane-2,3-diol 36150-04-6 C10H20O3
Lup-20(29)-ene-1β,3α-diol Lup-20(29)-ene-1β,3α-diol 6610-56-6 C30H50O2
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