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Terpenes

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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:
Parthenolide
CAS:
20554-84-1
MF:
C15H20O3
Structure:
Chemical Name:
Baccatine III
CAS:
27548-93-2
MF:
C31H38O11
Structure:
Chemical Name:
ABIETIC ACID
CAS:
514-10-3
MF:
C20H30O2
Structure:
Chemical Name:
Costunolide
CAS:
553-21-9
MF:
C15H20O2
Structure:
Chemical Name:
Ginkgolide A
CAS:
15291-75-5
MF:
C20H24O9
Structure:
Chemical Name:
L(-)-Borneol
CAS:
464-45-9
MF:
C10H18O
Structure:
Chemical Name:
(+)-Abscisic acid
CAS:
21293-29-8
MF:
C15H20O4
Structure:
Chemical Name:
Ginkgolide B
CAS:
15291-77-7
MF:
C20H24O10
Structure:
Chemical Name:
Dehydrocostus lactone
CAS:
477-43-0
MF:
C15H18O2
Structure:
Chemical Name:
Ginkgolide C
CAS:
15291-76-6
MF:
C20H24O11
Structure:
Chemical Name:
Madecassic acid
CAS:
18449-41-7
MF:
C30H48O6
Structure:
Chemical Name:
Squalene
CAS:
111-02-4
MF:
C30H50
Structure:
Chemical Name:
DIACETYL BENZOYL LATHYROL
CAS:
218916-52-0
MF:
C31H38O7
Structure:
Chemical Name:
WILFORLIDE A
CAS:
84104-71-2
MF:
C30H46O3
Structure:
Chemical Name:
Hederagenin
CAS:
465-99-6
MF:
C30H48O4
Structure:
Chemical Name:
Saikosaponin B2
CAS:
58316-41-9
MF:
C42H68O13
Structure:
Chemical Name:
7-Xylosyl-10-deacetyltaxol
CAS:
90332-63-1
MF:
C50H57NO17
Structure:
Chemical Name:
beta-Amyrin
CAS:
559-70-6
MF:
C30H50O
Structure:
Chemical Name:
Taraxasterol
CAS:
1059-14-9
MF:
C30H50O
Structure:
Chemical Name:
KIRENOL
CAS:
52659-56-0
MF:
C20H34O4
Structure:
Chemical Name:
ponicidin
CAS:
52617-37-5
MF:
C20H26O6
Structure:
Chemical Name:
UVAOL
CAS:
545-46-0
MF:
C30H50O2
Structure:
Chemical Name:
benzoylpaeoniflorin
CAS:
38642-49-8
MF:
C30H32O12
Structure:
Chemical Name:
QUASSIN
CAS:
76-78-8
MF:
C22H28O6
Structure:
Chemical Name:
ALPHA-HEDERIN
CAS:
27013-91-8
MF:
C41H66O12
Structure:
Chemical Name:
Maslinic acid
CAS:
4373-41-5
MF:
C30H48O4
Structure:
Chemical Name:
ALPHA-BOSWELLIC ACID
CAS:
471-66-9
MF:
C30H48O3
Structure:
Chemical Name:
LUPENONE
CAS:
1617-70-5
MF:
C30H48O
Structure:
Chemical Name:
Ganoderol B
CAS:
104700-96-1
MF:
C30H48O2
Structure:
Chemical Name:
Diosbulbin B
CAS:
20086-06-0
MF:
C19H20O6
Structure:
Chemical Name:
(13α,14β,17α,20S,23R,24S)-21,24-Epoxy-23,25-dihydroxy-5α-lanost-7-en-3-one
CAS:
6985-35-9
MF:
C30H48O4
Structure:
Chemical Name:
D:B-Friedo-B':A'-neogammacer-5-en-3β-ol
CAS:
1615-94-7
MF:
C30H50O
Structure:
Chemical Name:
Gadermandiol
CAS:
107900-76-5
MF:
C30H48O3
Structure:
Chemical Name:
7-EPI-10-DEACETYLTAXOL
CAS:
78454-17-8
MF:
C45H49NO13
Structure:
Chemical Name:
PIMARIC ACID
CAS:
127-27-5
MF:
C20H30O2
Structure:
Chemical Name:
WILFORGINE
CAS:
37239-47-7
MF:
C41H47NO19
Structure:
Chemical Name:
3-Epikatonic acid
CAS:
76035-62-6
MF:
C30H48O3
Structure:
Chemical Name:
Phytolaccagenin
CAS:
1802-12-6
MF:
C31H48O7
Structure:
Chemical Name:
(4aR)-5β-[2-(3-Furyl)ethyl]-3,4,4aβ,5,6,7,8,8a-octahydro-5,6α,8aα-trimethyl-1-naphthalenecarboxylic acid
CAS:
1782-65-6
MF:
C20H28O3
Structure:
Chemical Name:
3-O-alpha-L-Arabinopyranosylpomolic acid beta-D-glucopyranosyl ester
CAS:
35286-58-9
MF:
C41H66O13
Structure:
Chemical Name:
TOTAROL
CAS:
511-15-9
MF:
C20H30O
Structure:
Chemical Name:
Atractylenolide-1
CAS:
73069-13-3
MF:
C15H18O2
Structure:
Chemical Name:
moronic acid
CAS:
6713-27-5
MF:
C30H46O3
Structure:
Chemical Name:
steviolbioside
CAS:
41093-60-1
MF:
C32H50O13
Structure:
Chemical Name:
Carabrone
CAS:
1748-81-8
MF:
C15H20O3
Structure:
Chemical Name:
Ziyuglycoside II
CAS:
35286-59-0
MF:
C35H56O8
Structure:
Chemical Name:
Dehydroabietic acid
CAS:
1740-19-8
MF:
C20H28O2
Structure:
Chemical Name:
EFFUSANIN A
CAS:
30220-43-0
MF:
C20H28O5
Structure:
Chemical Name:
FRIEDELAN-3BETA-OL
CAS:
16844-71-6
MF:
C30H52O
Structure:
Chemical Name:
Nerolidol
CAS:
40716-66-3
MF:
C15H26O
Structure:
Chemical Name:
FRIEDELIN
CAS:
559-74-0
MF:
C30H50O
Structure:
Chemical Name:
Betulonicacid
CAS:
4481-62-3
MF:
C30H46O3
Structure:
Chemical Name:
Erythrodiol
CAS:
545-48-2
MF:
C30H50O2
Structure:
Chemical Name:
PROTOPANAXTRIOL
CAS:
34080-08-5
MF:
C30H52O4
Structure:
Chemical Name:
Vitexilactone
CAS:
61263-49-8
MF:
C22H34O5
Structure:
Chemical Name:
amyrin palmitate
CAS:
5973-06-8
MF:
C46H80O2
Structure:
Chemical Name:
taraxerol acetate
CAS:
2189-80-2
MF:
C32H52O2
Structure:
Chemical Name:
ACETYLISOCUPRESSICACID
CAS:
52992-82-2
MF:
C22H34O4
Structure:
Chemical Name:
(2α,3α)-2,3-Dihydroxy-olean-12-en-28-oic acid
CAS:
26563-68-8
MF:
C30H48O4
Structure:
Chemical Name:
18BETA(H)-OLEAN-12-ENE-3,11-DIONE
CAS:
2935-32-2
MF:
C30H46O2
Structure:
Chemical Name:
Nsc692967
CAS:
135683-73-7
MF:
C20H32O3
Structure:
Chemical Name:
DIPTEROCARPOL
CAS:
471-69-2
MF:
C30H50O2
Structure:
Chemical Name:
18BETA(H)-OLEAN-12-EN-3-ONE
CAS:
638-97-1
MF:
C30H48O
Structure:
Chemical Name:
CIMICIFUGOSIDE M
CAS:
256925-92-5
MF:
C35H56O9
Structure:
Chemical Name:
Pygenic acid A
CAS:
52213-27-1
MF:
C30H48O4
Structure:
Chemical Name:
(20S,24R)-12β,25-Dihydroxy-20,24-epoxydammarane-3-one
CAS:
25279-15-6
MF:
C30H50O4
Structure:
Chemical Name:
WILFORINE
CAS:
11088-09-8
MF:
C43H49NO18
Structure:
Chemical Name:
Baccatin
CAS:
66107-60-6
MF:
C29H46O4
Structure:
Chemical Name:
DARUTIGENOL
CAS:
5940-00-1
MF:
C20H34O3
Structure:
Chemical Name:
3-Phenanthrenol, 4b,5,6,7,8,8a,9,10-octahydro-4b,8,8-trimethyl-2-(1-methylethyl)-, (4bS,8aS)-
CAS:
514-62-5
MF:
C20H30O
Structure:
Chemical Name:
3-Deacetylsalannin
CAS:
1110-56-1
MF:
C32H42O8
Structure:
Chemical Name:
taraxasteryl acetate
CAS:
6426-43-3
MF:
C32H52O2
Structure:
Chemical Name:
(23R,24S)-24,25-Epoxy-23-hydroxy-5α-tirucall-7-en-3-one
CAS:
115404-57-4
MF:
C30H48O3
Structure:
Chemical Name:
Cycloastragenol
CAS:
78574-94-4
MF:
C30H50O5
Structure:
Chemical Name:
NIMBIN
CAS:
5945-86-8
MF:
C30H36O9
Structure:
Chemical Name:
FITONE
CAS:
502-69-2
MF:
C18H36O
Structure:
Chemical Name:
CIMIGENOL 3-O-BETA-D-XYLOPYRANOSIDE
CAS:
27994-11-2
MF:
C35H56O9
Structure:
Chemical Name:
Ganodermenonol
CAS:
104700-97-2
MF:
C30H46O2
Structure:
Chemical Name:
cedrelone
CAS:
1254-85-9
MF:
C26H30O5
Structure:
Chemical Name:
serrat-14-ene-3,21-diol
CAS:
2239-24-9
MF:
C30H50O2
Structure:
Chemical Name:
2α,3β,19α-Trihydroxyolean-12-en-28-oic acid
CAS:
31298-06-3
MF:
C30H48O5
Structure:
Chemical Name:
9,19-Cyclo-5α-lanost-25-ene-3β,24-diol
CAS:
10388-48-4
MF:
C30H50O2
Structure:
Chemical Name:
Betulin caffeate
CAS:
89130-86-9
MF:
C39H56O5
Structure:
Chemical Name:
Lophanthoidin B
CAS:
120462-42-2
MF:
C24H32O8
Structure:
Chemical Name:
Quivic acid
CAS:
465-74-7
MF:
C30H46O5
Structure:
Chemical Name:
Uncaric acid
CAS:
123135-05-7
MF:
C30H48O5
Structure:
Chemical Name:
Euphorbia factor L1
CAS:
76376-43-7
MF:
C32H40O8
Structure:
Chemical Name:
13-Hydroxy-8,11,13-podocarpatrien-18-oic acid
CAS:
61597-83-9
MF:
C17H22O3
Structure:
Chemical Name:
ALPHA-ONOCERIN
CAS:
511-01-3
MF:
C30H50O2
Structure:
Chemical Name:
alpha-Amyrenyl acetate
CAS:
863-76-3
MF:
C32H52O2
Structure:
Chemical Name:
(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
CAS:
514-07-8
MF:
C30H48O
Structure:
Chemical Name:
ailanthone
CAS:
981-15-7
MF:
C20H24O7
Structure:
Chemical Name:
artemisic acid
CAS:
80286-58-4
MF:
C15H22O2
Structure:
Chemical Name:
DESACETYLNIMBIN
CAS:
18609-16-0
MF:
C28H34O8
Structure:
Chemical Name:
Rutundic acid
CAS:
20137-37-5
MF:
C30H48O5
Structure:
Chemical Name:
4-Hydroxy-2,6,6-trimethyl-1-cyclohexenecarboxylic acid
CAS:
62218-55-7
MF:
C10H16O3
Structure:
Chemical Name:
3-Oxo-olean-12-en-28-oic acid
CAS:
17990-42-0
MF:
C30H46O3
Structure:
Chemical Name:
1-(4-Isopropyl-1-methyl-4-pentenyl)-3a,6,6,12a-tetramethyltetradecahyd ro-1H-cyclopenta[a]cyclopropa[e]phenanthren-7-yl acetate
CAS:
1259-94-5
MF:
C33H54O2
Structure:
Chemical Name:
[(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
CAS:
1616-93-9
MF:
C32H52O2
Structure:
Chemical Name:
6β,16-Dihydroxykauran-2β-yl β-D-glucopyranoside
CAS:
53452-34-9
MF:
C26H44O8