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
Honokiol Honokiol 564-73-8 C20H30O2
(12R)-21-Acetyloxy-13-deoxy-5β-hydroxyenmein (12R)-21-Acetyloxy-13-deoxy-5β-hydroxyenmein 83150-97-4 C22H28O8
[3S,3aα,7aα,(-)]-3a,6,7,7a-Tetrahydro-6β-hydroxy-3α-[(benzoyloxy)methyl]-6-methylbenzofuran-2,5(3H,4H)-dione [3S,3aα,7aα,(-)]-3a,6,7,7a-Tetrahydro-6β-hydroxy-3α-[(benzoyloxy)methyl]-6-methylbenzofuran-2,5(3H,4H)-dione 98751-77-0 C17H18O6
3β-Hydroxy-1-oxoolean-12-en-28-oic acid 3β-Hydroxy-1-oxoolean-12-en-28-oic acid 14356-51-5 C30H46O4
2α,3α,19,24-Tetrahydroxyurs-12-en-28-oic acid 2α,3α,19,24-Tetrahydroxyurs-12-en-28-oic acid 89786-84-5 C30H48O6
2α,19α-Dihydroxyursolic acid 2α,19α-Dihydroxyursolic acid 13850-16-3 C30H48O5
Alepterolic acid Alepterolic acid 63399-38-2 C20H32O3
ceanothic acid ceanothic acid 21302-79-4 C30H46O5
paeoniflorigenone paeoniflorigenone 80454-42-8 C17H18O6
salaspermic acid salaspermic acid 71247-78-4 C30H48O4
5,19-Epoxy-19,25-dimethoxycucurbita-6,23-dien-3-ol 5,19-Epoxy-19,25-dimethoxycucurbita-6,23-dien-3-ol 85372-70-9 C32H52O4
(13α,14β,17α,20S,23R,24S)-21,25-Epoxy-23,24-dihydroxylanost-7-en-3-one (13α,14β,17α,20S,23R,24S)-21,25-Epoxy-23,24-dihydroxylanost-7-en-3-one 73891-72-2 C30H48O4
4β-Carboxy-19-nortotarol 4β-Carboxy-19-nortotarol 55102-39-1 C20H28O3
ent-16beta,17-Isopropylidenedioxykaurane ent-16beta,17-Isopropylidenedioxykaurane 58493-71-3 C23H38O2
Paclitaxel IMpurity F Paclitaxel IMpurity F 153083-53-5 C47H59NO14
β-Peltoboykinolic acid β-Peltoboykinolic acid 24778-48-1 C30H48O3
Metasequoic acid A Metasequoic acid A 113626-22-5 C20H30O2
Lupeol 3-hydroxyoctadecanoate Lupeol 3-hydroxyoctadecanoate 108885-61-6 C48H84O3
Nemoralisin Nemoralisin 942480-13-9 C20H28O4
Scutebata A Scutebata A 1207181-57-4 C36H40O10
Scutebata G Scutebata G 1207181-63-2 C40H41NO9
Walsuroid B Walsuroid B 942582-15-2 C26H30O6
2,5,7,8,9,14-Hexaacetoxy-3-benzoyloxy-15-hydroxyjatropha-6(17),11E-diene 2,5,7,8,9,14-Hexaacetoxy-3-benzoyloxy-15-hydroxyjatropha-6(17),11E-diene 210108-86-4 C39H50O15
9α,13α-Epidioxyabiet-8(14)-en-18-oic acid 9α,13α-Epidioxyabiet-8(14)-en-18-oic acid 116499-73-1 C20H30O4
Methyl dodonate A Methyl dodonate A 349534-70-9 C21H28O4
Scutebarbatine W Scutebarbatine W 1312716-25-8 C33H37NO8
ent-3β-Tigloyloxykaur-16-en-19-oic acid ent-3β-Tigloyloxykaur-16-en-19-oic acid 79406-09-0 C25H36O4
Lasiodonin Lasiodonin 38602-52-7 C20H28O6
Triptobenzene H Triptobenzene H 146900-55-2 C21H28O4
7-O-Acetylneocaesalpin N 7-O-Acetylneocaesalpin N 1309079-08-0 C25H34O10
CaesalMin E CaesalMin E 204185-91-1 C26H36O9
ent-3β,18-Dihydroxylabda
-8(17),13E-dien-15-oic acid ent-3β,18-Dihydroxylabda -8(17),13E-dien-15-oic acid 99624-39-2 C20H32O4
Minaxin C Minaxin C 1418150-06-7 C26H38O12
Sageone Sageone 142546-15-4 C19H24O3
Tinospinoside C Tinospinoside C 1383977-51-2 C27H36O12
Scutebata F Scutebata F 1207181-62-1 C30H37NO9
15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene 15,16-Epoxy-12R-hydroxylabda-8(17),13(16),14-triene 61597-55-5 C20H30O2
2,5,7,14-Tetraacetoxy-3-benzoyloxy-8,15-dihydroxy-9-nicotinoyloxyjatropha-6(17),11E-diene 2,5,7,14-Tetraacetoxy-3-benzoyloxy-8,15-dihydroxy-9-nicotinoyloxyjatropha-6(17),11E-diene 210108-89-7 C41H49NO14
3,23-Dioxo-9,19-cyclolanost-24-en-26-oic acid 3,23-Dioxo-9,19-cyclolanost-24-en-26-oic acid 870456-88-5 C30H44O4
3-Oxotirucalla-7,24-dien-21-oic acid 3-Oxotirucalla-7,24-dien-21-oic acid 82464-35-5 C30H46O3
(-)-6beta-Hydroxy-5beta,8beta,9beta,10alpha-cleroda-3,13-dien-16,15-olid-18-oic acid (-)-6beta-Hydroxy-5beta,8beta,9beta,10alpha-cleroda-3,13-dien-16,15-olid-18-oic acid 771493-42-6 C20H28O5
(9aS)-7,8,9,9a-Tetrahydro-9a-hydroxy-6-methyl-9-(1-methylethenyl)-2-(1-methylethyl)-1H-phenalen-1-one (9aS)-7,8,9,9a-Tetrahydro-9a-hydroxy-6-methyl-9-(1-methylethenyl)-2-(1-methylethyl)-1H-phenalen-1-one 453518-30-4 C20H24O2
Acantrifoic acid A Acantrifoic acid A 654663-85-1 C32H48O7
Isovouacapenol C Isovouacapenol C 455255-15-9 C27H34O5
Verbenacine Verbenacine 717901-03-6 C20H30O3
Borapetoside D Borapetoside D 151200-48-5 C33H46O16
ent-Atisane-3β,16α,17-triol ent-Atisane-3β,16α,17-triol 115783-44-3 C20H34O3
12-O-Methylcarnosic acid 12-O-Methylcarnosic acid 62201-71-2 C21H30O4
3,4-seco-Olean-12-en-4-ol-3,28-dioic acid 3,4-seco-Olean-12-en-4-ol-3,28-dioic acid 182249-69-0 C30H48O5
7-O-Acetylbonducellpin C 7-O-Acetylbonducellpin C 197781-86-5 C25H34O8
ent-11α-Hydroxy-15-oxokaur-16-en-19-oic acid ent-11α-Hydroxy-15-oxokaur-16-en-19-oic acid 57719-81-0 C20H28O4
TAXININE TAXININE 3835-52-7 C35H42O9
tripterifordin tripterifordin 139122-81-9 C20H30O3
paeonilactone A paeonilactone A 98751-79-2 C10H14O4
Curzerenone Curzerenone 20493-56-5 C15H18O2
cauloside A cauloside A 17184-21-3 C35H56O8
jolkinolide E jolkinolide E 54494-34-7 C20H28O2
galanolactone galanolactone 115753-79-2 C20H30O3
Coronarin B Coronarin B 119188-38-4 C20H30O4
trans-Communol trans-Communol 10178-31-1 C20H32O
Methyl hydroxyangolensate Methyl hydroxyangolensate 22255-07-8 C27H34O8
[16R,(-)]-Kaurane-6β,16α,17-triol [16R,(-)]-Kaurane-6β,16α,17-triol 7047-54-3 C20H34O3
(1S)-1,2,3,3a,5aβ,6,10b,10cβ-Octahydro-1,2α,6α-trihydroxy-3aβ,10bα-dimethyl-7-isopropyl-4H,9H-furo[2',3',4':4,5]naphtho[2,1-c]pyran-4,9-dione (1S)-1,2,3,3a,5aβ,6,10b,10cβ-Octahydro-1,2α,6α-trihydroxy-3aβ,10bα-dimethyl-7-isopropyl-4H,9H-furo[2',3',4':4,5]naphtho[2,1-c]pyran-4,9-dione 19891-51-1 C19H24O7
Hopane-3β,22-diol Hopane-3β,22-diol 22149-65-1 C30H52O2
25-Hydroxycycloart-23-en-3-one 25-Hydroxycycloart-23-en-3-one 148044-47-7 C30H48O2
6,19-Dihydroxyurs-12-en-3-oxo-28-oic acid 6,19-Dihydroxyurs-12-en-3-oxo-28-oic acid 194027-11-7 C30H46O5
6-O-Nicotiylbarbatin C 6-O-Nicotiylbarbatin C 1015776-92-7 C26H31NO6
Khayaleid E Khayaleid E 1220508-29-1 C29H34O9
Sootepin D Sootepin D 1154518-97-4 C31H48O4
Hedragonic acid Hedragonic acid 466-02-4 C29H44O3
16-Hydroxy-2-oxocleroda-3,13-dien-15,16-olide 16-Hydroxy-2-oxocleroda-3,13-dien-15,16-olide 165459-53-0 C20H28O4
3-O-(E)-Hydroxycinnamoyl oleanolic acid 3-O-(E)-Hydroxycinnamoyl oleanolic acid 151334-06-4 C39H54O5
(2alpha,3beta)-2,3-Dihydroxyoleana-11,13(18)-dien-28-oic acid (2alpha,3beta)-2,3-Dihydroxyoleana-11,13(18)-dien-28-oic acid 71850-15-2 C30H46O4
ent-Labda-8(17),13Z-diene-
15,16,19-triol 19-O-glucoside ent-Labda-8(17),13Z-diene- 15,16,19-triol 19-O-glucoside 1245636-01-4 C26H44O8
Oleuropeic acid 8-O-glucoside Oleuropeic acid 8-O-glucoside 865887-46-3 C16H26O8
Diosbulbin L Diosbulbin L 1236285-87-2 C19H22O7
Borapetoside E Borapetoside E 151200-49-6 C27H36O11
29-Nor-20-oxolupeol 29-Nor-20-oxolupeol 19891-85-1 C29H48O2
Hebeirubescensin H Hebeirubescensin H 887333-30-4 C20H28O7
2'-O-Benzoylpaeoniflorin 2'-O-Benzoylpaeoniflorin 1456598-64-3 C30H32O12
7,13-Dideacetyl-9,10-didebenzoyltaxchinin C 7,13-Dideacetyl-9,10-didebenzoyltaxchinin C 156497-25-5 C29H38O10
7-O-MethylrosManol 7-O-MethylrosManol 113085-62-4 C21H28O5
ent-Kaurane-16β,19,20-triol ent-Kaurane-16β,19,20-triol 167898-32-0 C20H34O3
Neocaesalpin O Neocaesalpin O 1053189-53-9 C26H34O10
Serrin A Serrin A 845959-98-0 C22H30O6
SwieteMahalactone SwieteMahalactone 1514669-21-6 C27H30O10
7-Deacetoxytaxinine J 7-Deacetoxytaxinine J 18457-45-9 C37H46O10
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