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
15-Methoxypinusolidic acid 15-Methoxypinusolidic acid 769928-72-5 C21H30O5
(6E)-3,7-Dimethyl-8-(β-D-glucopyranosyloxy)-1,6-octadiene-3-ol (6E)-3,7-Dimethyl-8-(β-D-glucopyranosyloxy)-1,6-octadiene-3-ol 64776-96-1 C16H28O7
(7S,15R)-6β,15-Diacetoxy-7α,20-epoxy-7-hydroxykaura-2,16-dien-1-one (7S,15R)-6β,15-Diacetoxy-7α,20-epoxy-7-hydroxykaura-2,16-dien-1-one 51419-51-3 C24H30O7
(4S)-C(14a)-Homo-27-norgammacer-14-ene-3α,20β,21β,23-tetrol (4S)-C(14a)-Homo-27-norgammacer-14-ene-3α,20β,21β,23-tetrol 53755-76-3 C30H50O4
1-Hydroxy-2-oxopomolic acid 1-Hydroxy-2-oxopomolic acid 217466-37-0 C30H46O6
2,24-Dihydroxyursolic acid 2,24-Dihydroxyursolic acid 143839-02-5 C30H48O5
20,24-Dihydroxydammar-25-en-3-one 20,24-Dihydroxydammar-25-en-3-one 75069-59-9 C30H50O3
3,4-Secotirucalla-4(28),7,24-triene-3,26-dioic acid 3,4-Secotirucalla-4(28),7,24-triene-3,26-dioic acid 159623-48-0 C30H46O4
3-Acetoxy-24-hydroxydammara-20,25-diene 3-Acetoxy-24-hydroxydammara-20,25-diene 143519-04-4 C32H52O3
3-O-(E)-p-Coumaroylbetulin 3-O-(E)-p-Coumaroylbetulin 144424-80-6 C39H56O4
grandiflorenic acid grandiflorenic acid 22338-67-6 C20H28O2
MAOECRYSTAL B MAOECRYSTAL B 96850-29-2 C22H28O6
5α-Cycloart-23-ene-3β,25-diol 5α-Cycloart-23-ene-3β,25-diol 14599-48-5 C30H50O2
3β,11α-Dihydroxyoleana-12-ene 3β,11α-Dihydroxyoleana-12-ene 5282-14-4 C30H50O2
6-Epidemethylesquirolin D 6-Epidemethylesquirolin D 165074-00-0 C20H28O5
Bauerel acetate Bauerel acetate 17020-04-1 C32H52O2
Clerodermic acid methyl ester Clerodermic acid methyl ester 67650-47-9 C21H30O4
Cycloartane-3,24,25-triol Cycloartane-3,24,25-triol 57576-29-1 C30H52O3
16-O-Acetyldarutigel 16-O-Acetyldarutigel 1188282-01-0 C22H36O4
2,6,16-Kauranetriol 2,6,16-Kauranetriol 41530-90-9 C20H34O3
23-deoxojessic acid 23-deoxojessic acid 215609-93-1 C31H50O4
3-Hydroxy-11-ursen-28,13-olide 3-Hydroxy-11-ursen-28,13-olide 35959-05-8 C30H46O3
Diosbulbin J Diosbulbin J 1187951-06-9 C19H22O8
ent-3-Oxokauran-17-oic acid ent-3-Oxokauran-17-oic acid 151561-88-5 C20H30O3
ent-9-Hydroxy-15-oxo-19-kauraic acid ent-9-Hydroxy-15-oxo-19-kauraic acid 77658-45-8 C20H30O4
Glaucin B Glaucin B 115458-73-6 C28H32O10
Heudelotine Heudelotine 133453-58-4 C18H20O2
Jangomolide Jangomolide 93767-25-0 C26H28O8
Limonexic acid Limonexic acid 99026-99-0 C26H30O10
Momordicoside G Momordicoside G 81371-54-2 C37H60O8
Pyrocincholic acid methyl ester Pyrocincholic acid methyl ester 107160-24-7 C30H48O3
Rosthornin A Rosthornin A 125164-55-8 C22H32O5
Sorghumol Sorghumol 90582-44-8 C30H50O
Quinovic acid 3-O-(6-deoxy-beta-D-glucopyranoside) 28-O-beta-D-glucopyranosyl ester Quinovic acid 3-O-(6-deoxy-beta-D-glucopyranoside) 28-O-beta-D-glucopyranosyl ester 124727-10-2 C42H66O14
2-Oxokolavenol 2-Oxokolavenol 130395-82-3 C20H32O2
3,22-Dihydroxyolean-12-en-29-oic acid 3,22-Dihydroxyolean-12-en-29-oic acid 808769-54-2 C30H48O4
Epitaraxerol Epitaraxerol 20460-33-7 C30H50O
Paniculoside I Paniculoside I 60129-63-7 C26H40O8
Acetylsventenic acid Acetylsventenic acid 126737-42-6 C22H32O4
[1R-(1alpha,4abeta,10aalpha)]-1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethylphenanthren-1-methanol [1R-(1alpha,4abeta,10aalpha)]-1,2,3,4,4a,9,10,10a-octahydro-7-isopropyl-1,4a-dimethylphenanthren-1-methanol 3772-55-2 C20H30O
ebericol ebericol 6890-88-6 C31H52O
Arjunolic acid Arjunolic acid 465-00-9 C30H48O5
24,25-dihydroxycycloartan-3-one 24,25-dihydroxycycloartan-3-one 155060-48-3 C30H50O3
3β,7β,19α-Trihydroxy-5α-arbor-9(11)-ene 3β,7β,19α-Trihydroxy-5α-arbor-9(11)-ene 130288-60-7 C30H50O3
29-Hydroxyfriedelane-3-one 29-Hydroxyfriedelane-3-one 39903-21-4 C30H50O2
(20S,24S)-20,24-Epoxy-25-hydroxy-3,4-seco-5α-dammar-4(28)-en-3-oic acid (20S,24S)-20,24-Epoxy-25-hydroxy-3,4-seco-5α-dammar-4(28)-en-3-oic acid 56421-13-7 C30H50O4
(24S)-20,24-Epoxy-25-hydroxy-5α-dammaran-3-one (24S)-20,24-Epoxy-25-hydroxy-5α-dammaran-3-one 35761-54-7 C30H50O3
(24E)-3β-Hydroxy-9β,19-cyclo-5α-lanost-24-en-26-oic acid (24E)-3β-Hydroxy-9β,19-cyclo-5α-lanost-24-en-26-oic acid 4184-34-3 C30H48O3
1β-Hydroxylup-20(29)-en-3-one 1β-Hydroxylup-20(29)-en-3-one 23963-54-4 C30H48O2
12-Hydroxyabietic acid 12-Hydroxyabietic acid 3484-61-5 C20H30O3
1-Deacetylnimbolinin B 1-Deacetylnimbolinin B 76689-98-0 C33H44O9
2,3-O-Isopropylidenyl euscaphic acid 2,3-O-Isopropylidenyl euscaphic acid 220880-90-0 C33H52O5
2-Epitormentic acid 2-Epitormentic acid 119725-19-8 C30H48O5
3,6,19,23-Tetrahydroxy-12-ursen-28-oic acid 3,6,19,23-Tetrahydroxy-12-ursen-28-oic acid 91095-51-1 C30H48O6
16-Kaurene-2,6,15-triol 16-Kaurene-2,6,15-triol 53452-32-7 C20H32O3
6-Deoxy-9alpha-hydroxycedrodorin 6-Deoxy-9alpha-hydroxycedrodorin 247036-52-8 C27H34O9
3α,21β-Dihydroxy-C(14a)-homo-27-norgammaceran-14-en-16-one 3α,21β-Dihydroxy-C(14a)-homo-27-norgammaceran-14-en-16-one 24513-51-7 C30H48O3
ent-Isopimara-8(14),15-diene-3β-ol ent-Isopimara-8(14),15-diene-3β-ol 4728-30-7 C20H32O
Lup-20(29)-ene-2α,3β-diol Lup-20(29)-ene-2α,3β-diol 61448-03-1 C30H50O2
(4aR)-5β-[2-(3-Furyl)ethyl]-5,6α-dimethyl-8aα-(hydroxymethyl)-3,4,4aβ,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid (4aR)-5β-[2-(3-Furyl)ethyl]-5,6α-dimethyl-8aα-(hydroxymethyl)-3,4,4aβ,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid 18411-75-1 C20H28O4
Methyl acetoxyangolensate Methyl acetoxyangolensate 16566-88-4 C29H36O9
15-Deoxoeucosterol 15-Deoxoeucosterol 81241-53-4 C29H46O4
1-Decarboxy-3-oxo-ceathic acid 1-Decarboxy-3-oxo-ceathic acid 214150-74-0 C29H44O3
2,16-Kauranediol 2-O-beta-D-allopyraside 2,16-Kauranediol 2-O-beta-D-allopyraside 474893-07-7 C26H44O7
2,3,23-Trihydroxy-12-oleanen-28-oic acid 2,3,23-Trihydroxy-12-oleanen-28-oic acid 102519-34-6 C30H48O5
2,6-Dimethyl-7-octene-2,3,6-triol 2,6-Dimethyl-7-octene-2,3,6-triol 73815-21-1 C10H20O3
24,25-Epoxytirucall-7-en-3,23-dione 24,25-Epoxytirucall-7-en-3,23-dione 890928-81-1 C30H46O3
26-r-8-oxo-alpha-ocerin 26-r-8-oxo-alpha-ocerin 125124-68-7 C29H48O3
Betulin palmitate Betulin palmitate 582315-55-7 C46H80O3
Demethoxydeacetoxypseudolaric acid B Demethoxydeacetoxypseudolaric acid B 82508-36-9 C20H24O7
Forskolin G Forskolin G 473981-11-2 C24H36O7
Lophanthoidin E Lophanthoidin E 120462-45-5 C22H30O7
Picrasin B acetate Picrasin B acetate 30315-04-9 C23H30O7
p-Menth-8-ene-1,2-diol p-Menth-8-ene-1,2-diol 57457-97-3 C10H18O2
Quivic acid 3-O-beta-D-glucoside Quivic acid 3-O-beta-D-glucoside 79955-41-2 C36H56O10
Taxayunnansin A Taxayunnansin A 153229-31-3 C35H44O13
Triptoquinide Triptoquinide 163513-81-3 C20H22O4
1,3-Diacetylvilasinin 1,3-Diacetylvilasinin 78012-28-9 C30H40O7
27-HydroxyMangiferonic acid 27-HydroxyMangiferonic acid 5132-66-1 C30H46O4
Hennadiol Hennadiol 20065-99-0 C30H50O2
oleuropeic acid oleuropeic acid 5027-76-9 C10H16O3
trichorabdal A trichorabdal A 85329-59-5 C20H26O5
pinusolidic acid pinusolidic acid 40433-82-7 C20H28O4
α-Amyrenone α-Amyrenone 20248-08-2 C30H48O
3β-Acetoxy-13-hydroxyurs-11-ene-28-oic acid lactone 3β-Acetoxy-13-hydroxyurs-11-ene-28-oic acid lactone 35959-08-1 C32H48O4
3-Deoxyryanodol 3-Deoxyryanodol 62394-04-1 C20H32O7
(24E)-3-Oxo-5α-lanosta-7,9(11),24-triene-26-al (24E)-3-Oxo-5α-lanosta-7,9(11),24-triene-26-al 104700-98-3 C30H44O2
8(17),12,14-Labdatriene-19-oic acid 8(17),12,14-Labdatriene-19-oic acid 2761-77-5 C20H30O2
(13E)-15-Hydroxy-8(17),13-labdadiene-19-al (13E)-15-Hydroxy-8(17),13-labdadiene-19-al 3650-31-5 C20H32O2
Glutina-5-ene-3β-ol Glutina-5-ene-3β-ol 545-24-4 C30H50O
(23R,24S)-23,24-Dihydroxy-25-methoxy-5α-tirucall-7-en-3-one (23R,24S)-23,24-Dihydroxy-25-methoxy-5α-tirucall-7-en-3-one 115334-04-8 C31H52O4
3β,22α-Dihydroxyolean-12-en-29-oic acid 3β,22α-Dihydroxyolean-12-en-29-oic acid 84108-17-8 C30H48O4
10,13-Dideoxy-10α,21-epoxy-5β-hydroxyenmein 10,13-Dideoxy-10α,21-epoxy-5β-hydroxyenmein 85287-60-1 C20H24O6
6-Hydroxy-2,6-dimethyl-2,7-octadieic acid 6-Hydroxy-2,6-dimethyl-2,7-octadieic acid 28420-25-9 C10H16O3
7,15-Dihydroxy-8(14)-podocarpen-13-one 7,15-Dihydroxy-8(14)-podocarpen-13-one 262355-96-4 C17H26O3
9-Hydroxydarutigel 9-Hydroxydarutigel 1188282-00-9 C20H34O4
Alstonic acid A Alstonic acid A 1159579-44-8 C30H48O3
Bulleyanin Bulleyanin 123043-54-9 C28H38O10
Cabraleahydroxylactone acetate Cabraleahydroxylactone acetate 35833-70-6 C29H46O4
Coronarin D methyl ether Coronarin D methyl ether 157528-81-9 C21H32O3
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