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
Parthenolide Parthenolide 20554-84-1 C15H20O3
Baccatine III Baccatine III 27548-93-2 C31H38O11
ABIETIC ACID ABIETIC ACID 514-10-3 C20H30O2
Costunolide Costunolide 553-21-9 C15H20O2
Ginkgolide A Ginkgolide A 15291-75-5 C20H24O9
L(-)-Borneol L(-)-Borneol 464-45-9 C10H18O
(+)-Abscisic acid (+)-Abscisic acid 21293-29-8 C15H20O4
Ginkgolide B Ginkgolide B 15291-77-7 C20H24O10
Dehydrocostus lactone Dehydrocostus lactone 477-43-0 C15H18O2
Ginkgolide C Ginkgolide C 15291-76-6 C20H24O11
Madecassic acid Madecassic acid 18449-41-7 C30H48O6
Squalene Squalene 111-02-4 C30H50
DIACETYL BENZOYL LATHYROL DIACETYL BENZOYL LATHYROL 218916-52-0 C31H38O7
WILFORLIDE A WILFORLIDE A 84104-71-2 C30H46O3
Hederagenin Hederagenin 465-99-6 C30H48O4
Saikosaponin B2 Saikosaponin B2 58316-41-9 C42H68O13
7-Xylosyl-10-deacetyltaxol 7-Xylosyl-10-deacetyltaxol 90332-63-1 C50H57NO17
beta-Amyrin beta-Amyrin 559-70-6 C30H50O
Taraxasterol Taraxasterol 1059-14-9 C30H50O
KIRENOL KIRENOL 52659-56-0 C20H34O4
ponicidin ponicidin 52617-37-5 C20H26O6
UVAOL UVAOL 545-46-0 C30H50O2
benzoylpaeoniflorin benzoylpaeoniflorin 38642-49-8 C30H32O12
QUASSIN QUASSIN 76-78-8 C22H28O6
ALPHA-HEDERIN ALPHA-HEDERIN 27013-91-8 C41H66O12
Maslinic acid Maslinic acid 4373-41-5 C30H48O4
ALPHA-BOSWELLIC ACID ALPHA-BOSWELLIC ACID 471-66-9 C30H48O3
LUPENONE LUPENONE 1617-70-5 C30H48O
Ganoderol B Ganoderol B 104700-96-1 C30H48O2
Diosbulbin B Diosbulbin B 20086-06-0 C19H20O6
(13α,14β,17α,20S,23R,24S)-21,24-Epoxy-23,25-dihydroxy-5α-lanost-7-en-3-one (13α,14β,17α,20S,23R,24S)-21,24-Epoxy-23,25-dihydroxy-5α-lanost-7-en-3-one 6985-35-9 C30H48O4
D:B-Friedo-B':A'-neogammacer-5-en-3β-ol D:B-Friedo-B':A'-neogammacer-5-en-3β-ol 1615-94-7 C30H50O
Gadermandiol Gadermandiol 107900-76-5 C30H48O3
7-EPI-10-DEACETYLTAXOL 7-EPI-10-DEACETYLTAXOL 78454-17-8 C45H49NO13
PIMARIC ACID PIMARIC ACID 127-27-5 C20H30O2
WILFORGINE WILFORGINE 37239-47-7 C41H47NO19
3-Epikatonic acid 3-Epikatonic acid 76035-62-6 C30H48O3
Phytolaccagenin Phytolaccagenin 1802-12-6 C31H48O7
(4aR)-5β-[2-(3-Furyl)ethyl]-3,4,4aβ,5,6,7,8,8a-octahydro-5,6α,8aα-trimethyl-1-naphthalenecarboxylic acid (4aR)-5β-[2-(3-Furyl)ethyl]-3,4,4aβ,5,6,7,8,8a-octahydro-5,6α,8aα-trimethyl-1-naphthalenecarboxylic acid 1782-65-6 C20H28O3
3-O-alpha-L-Arabinopyranosylpomolic acid beta-D-glucopyranosyl ester 3-O-alpha-L-Arabinopyranosylpomolic acid beta-D-glucopyranosyl ester 35286-58-9 C41H66O13
TOTAROL TOTAROL 511-15-9 C20H30O
Atractylenolide-1 Atractylenolide-1 73069-13-3 C15H18O2
moronic acid moronic acid 6713-27-5 C30H46O3
steviolbioside steviolbioside 41093-60-1 C32H50O13
Carabrone Carabrone 1748-81-8 C15H20O3
Ziyuglycoside II Ziyuglycoside II 35286-59-0 C35H56O8
DEHYDROABIETIC ACID DEHYDROABIETIC ACID 1740-19-8 C20H28O2
EFFUSANIN A EFFUSANIN A 30220-43-0 C20H28O5
FRIEDELAN-3BETA-OL FRIEDELAN-3BETA-OL 16844-71-6 C30H52O
Nerolidol Nerolidol 40716-66-3 C15H26O
FRIEDELIN FRIEDELIN 559-74-0 C30H50O
Betulonicacid Betulonicacid 4481-62-3 C30H46O3
Erythrodiol Erythrodiol 545-48-2 C30H50O2
PROTOPANAXTRIOL PROTOPANAXTRIOL 34080-08-5 C30H52O4
Vitexilactone Vitexilactone 61263-49-8 C22H34O5
amyrin palmitate amyrin palmitate 5973-06-8 C46H80O2
taraxerol acetate taraxerol acetate 2189-80-2 C32H52O2
ACETYLISOCUPRESSICACID ACETYLISOCUPRESSICACID 52992-82-2 C22H34O4
(2α,3α)-2,3-Dihydroxy-olean-12-en-28-oic acid (2α,3α)-2,3-Dihydroxy-olean-12-en-28-oic acid 26563-68-8 C30H48O4
18BETA(H)-OLEAN-12-ENE-3,11-DIONE 18BETA(H)-OLEAN-12-ENE-3,11-DIONE 2935-32-2 C30H46O2
Nsc692967 Nsc692967 135683-73-7 C20H32O3
DIPTEROCARPOL DIPTEROCARPOL 471-69-2 C30H50O2
18BETA(H)-OLEAN-12-EN-3-ONE 18BETA(H)-OLEAN-12-EN-3-ONE 638-97-1 C30H48O
CIMICIFUGOSIDE M CIMICIFUGOSIDE M 256925-92-5 C35H56O9
Pygenic acid A Pygenic acid A 52213-27-1 C30H48O4
(20S,24R)-12β,25-Dihydroxy-20,24-epoxydammarane-3-one (20S,24R)-12β,25-Dihydroxy-20,24-epoxydammarane-3-one 25279-15-6 C30H50O4
WILFORINE WILFORINE 11088-09-8 C43 H49 N O18
Baccatin Baccatin 66107-60-6 C29H46O4
DARUTIGENOL DARUTIGENOL 5940-00-1 C20H34O3
3-Phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-(1-methylethyl)-, (4bS,8aS)- 3-Phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-(1-methylethyl)-, (4bS,8aS)- 514-62-5 C20H30O
3-Deacetylsalannin 3-Deacetylsalannin 1110-56-1 C32H42O8
taraxasteryl acetate taraxasteryl acetate 6426-43-3 C32H52O2
(23R,24S)-24,25-Epoxy-23-hydroxy-5α-tirucall-7-en-3-one (23R,24S)-24,25-Epoxy-23-hydroxy-5α-tirucall-7-en-3-one 115404-57-4 C30H48O3
CYCLOASTRAGENOL CYCLOASTRAGENOL 78574-94-4 C30H50O5
NIMBIN NIMBIN 5945-86-8 C30H36O9
FITONE FITONE 502-69-2 C18H36O
CIMIGENOL 3-O-BETA-D-XYLOPYRANOSIDE CIMIGENOL 3-O-BETA-D-XYLOPYRANOSIDE 27994-11-2 C35H56O9
Ganodermenonol Ganodermenonol 104700-97-2 C30H46O2
cedrelone cedrelone 1254-85-9 C26H30O5
serrat-14-ene-3,21-diol serrat-14-ene-3,21-diol 2239-24-9 C30H50O2
2α,3β,19α-Trihydroxyolean-12-en-28-oic acid 2α,3β,19α-Trihydroxyolean-12-en-28-oic acid 31298-06-3 C30H48O5
9,19-Cyclo-5α-lanost-25-ene-3β,24-diol 9,19-Cyclo-5α-lanost-25-ene-3β,24-diol 10388-48-4 C30H50O2
Betulin caffeate Betulin caffeate 89130-86-9 C39H56O5
Lophanthoidin B Lophanthoidin B 120462-42-2 C24H32O8
Quivic acid Quivic acid 465-74-7 C30H46O5
Uncaric acid Uncaric acid 123135-05-7 C30H48O5
Euphorbia factor L1 Euphorbia factor L1 76376-43-7 C32H40O8
13-Hydroxy-8,11,13-podocarpatrien-18-oic acid 13-Hydroxy-8,11,13-podocarpatrien-18-oic acid 61597-83-9 C17H22O3
ALPHA-ONOCERIN ALPHA-ONOCERIN 511-01-3 C30H50O2
alpha-Amyrenyl acetate alpha-Amyrenyl acetate 863-76-3 C32H52O2
(4aS,6aS,6aR,8aR,12aS,14aS,14bS)-4,4,6a,6a,8a,11,11,14b-octamethyl-2,4 a,5,6,8,9,10,12,12a,13,14,14a-dodecahydro-1H-picen-3-one (4aS,6aS,6aR,8aR,12aS,14aS,14bS)-4,4,6a,6a,8a,11,11,14b-octamethyl-2,4 a,5,6,8,9,10,12,12a,13,14,14a-dodecahydro-1H-picen-3-one 514-07-8 C30H48O
ailanthone ailanthone 981-15-7 C20H24O7
artemisic acid artemisic acid 80286-58-4 C15H22O2
DESACETYLNIMBIN DESACETYLNIMBIN 18609-16-0 C28H34O8
Rutundic acid Rutundic acid 20137-37-5 C30H48O5
4-Hydroxy-2,6,6-trimethyl-1-cyclohexenecarboxylic acid 4-Hydroxy-2,6,6-trimethyl-1-cyclohexenecarboxylic acid 62218-55-7 C10H16O3
3-Oxo-olean-12-en-28-oic acid 3-Oxo-olean-12-en-28-oic acid 17990-42-0 C30H46O3
1-(4-Isopropyl-1-methyl-4-pentenyl)-3a,6,6,12a-tetramethyltetradecahyd ro-1H-cyclopenta[a]cyclopropa[e]phenanthren-7-yl acetate 1-(4-Isopropyl-1-methyl-4-pentenyl)-3a,6,6,12a-tetramethyltetradecahyd ro-1H-cyclopenta[a]cyclopropa[e]phenanthren-7-yl acetate 1259-94-5 C33H54O2
[(3S,4aS,6aR,6bS,8aR,12aR,14aS,14bS)-4,4,6a,6b,8a,11,11,14b-octamethyl -1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl] acetate [(3S,4aS,6aR,6bS,8aR,12aR,14aS,14bS)-4,4,6a,6b,8a,11,11,14b-octamethyl -1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl] acetate 1616-93-9 C32H52O2
6β,16-Dihydroxykauran-2β-yl β-D-glucopyranoside 6β,16-Dihydroxykauran-2β-yl β-D-glucopyranoside 53452-34-9 C26H44O8
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