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.

Click on the specific product, view the latest prices of the products, information, serving information
Structure Chemical Name CAS MF
Scutebata E Scutebata E 1207181-61-0 C28H40O9
(4α)-p-Menthane-1α,2β,8-triol (4α)-p-Menthane-1α,2β,8-triol 62014-81-7 C10H20O3
23-Hydroxybetulin 23-Hydroxybetulin 84414-40-4 C30H50O3
21αH-24-Norhopa-4(23),22(29)-diene-3β,6β-diol 21αH-24-Norhopa-4(23),22(29)-diene-3β,6β-diol 194613-74-6 C29H46O2
6α,16,18-Trihydroxycleroda
-3,13-dien-15,16-olide 6α,16,18-Trihydroxycleroda -3,13-dien-15,16-olide 1017233-48-5 C20H30O5
(1beta,6beta,7alpha,15beta,16alpha)-7,20-Epoxykaurane-1,6,7,15,16,17-hexol 6,17-diacetate (1beta,6beta,7alpha,15beta,16alpha)-7,20-Epoxykaurane-1,6,7,15,16,17-hexol 6,17-diacetate 90468-72-7 C24H36O9
Oleanolic acid-3-O-beta-D-xylopyranoside Oleanolic acid-3-O-beta-D-xylopyranoside 61617-29-6 C35H56O7
15-MethoxyMkapwanin 15-MethoxyMkapwanin 1309920-99-7 C21H28O5
DEACETYL-7-XYLOSYLCEPHALOMANNINE, 10-(RG) DEACETYL-7-XYLOSYLCEPHALOMANNINE, 10-(RG) 90332-64-2 C48H59NO17
1β-Hydroxyeuscaphic acid 1β-Hydroxyeuscaphic acid 120211-98-5 C30H48O6
12-DeMethylneocaesalpin F 12-DeMethylneocaesalpin F 1228964-10-0 C27H34O7
20-Deoxyingenol 3-angelate 20-Deoxyingenol 3-angelate 75567-38-3 C25H34O5
Taxacin Taxacin 117229-54-6 C44H48O15
Taxagifine Taxagifine 81489-69-2 C37H44O13
Aphadilactone B Aphadilactone B 1522004-68-7 C40H52O8
Mudanpioside H Mudanpioside H 231280-71-0 C30H32O14
Sahandol Sahandol 1452398-07-0 C20H24O2
Trigothysoid N Trigothysoid N 1501943-08-3 C44H58O13
14-deoxycaesalpin 14-deoxycaesalpin 279683-46-4 C24H34O6
euscaphic acid euscaphic acid 53155-25-2 C30H48O5
jolkinolide A jolkinolide A 37905-07-0 C20H26O3
MERCUSICACID MERCUSICACID 41787-69-3 C20H32O4
15-HYDROXY-7-OXODEHYDROABIETICACID 15-HYDROXY-7-OXODEHYDROABIETICACID 95416-25-4 C20H26O4
(1S)-1,2,3,4,4a,5,6,6aα,7,11,11aβ,11b-Dodecahydro-4,4,7,11bα-tetramethylphenanthro[3,2-b]furan-1,4aβ,5β,6α,7α-pentol (1S)-1,2,3,4,4a,5,6,6aα,7,11,11aβ,11b-Dodecahydro-4,4,7,11bα-tetramethylphenanthro[3,2-b]furan-1,4aβ,5β,6α,7α-pentol 7716-14-5 C20H30O6
(4S)-Kaurane-2β,16,19-triol (4S)-Kaurane-2β,16,19-triol 67349-43-3 C20H34O3
Imbricatoloic acid Imbricatoloic acid 6832-60-6 C20H34O3
22-Hydroxy-3-oxoolean-12-en-29-oic acid 22-Hydroxy-3-oxoolean-12-en-29-oic acid 144629-84-5 C30H46O4
5,19-Epoxy-25-methoxycucurbita-6,23-dien-3-ol 5,19-Epoxy-25-methoxycucurbita-6,23-dien-3-ol 81910-39-6 C31H50O3
Arteannuin M Arteannuin M 207446-90-0 C15H24O4
Diosbulbin I Diosbulbin I 1187951-05-8 C29H30O8
ent-17-Hydroxykauran-3-one ent-17-Hydroxykauran-3-one 960589-81-5 C20H32O2
Scutebata B Scutebata B 1207181-58-5 C35H39NO10
3α-Angeloyloxypterokaurene L3 3α-Angeloyloxypterokaurene L3 79406-11-4 C25H36O5
Melilotigenin C Melilotigenin C 188970-21-0 C30H48O3
Methyl dodonate A acetate Methyl dodonate A acetate 349487-98-5 C23H30O5
Trigoxyphin A Trigoxyphin A 1236874-00-2 C34H34O9
ent-11alpha-Hydroxyabieta-8(14),13(15)-dien-16,12alpha-olide ent-11alpha-Hydroxyabieta-8(14),13(15)-dien-16,12alpha-olide 130466-20-5 C20H28O3
barbinervic acid barbinervic acid 64199-78-6 C30H48O5
macrocalin A macrocalin A 10391-08-9 C20H26O5
galloylpaeoniflorin galloylpaeoniflorin 122965-41-7 C30H32O15
Sculponeatin K Sculponeatin K 477529-70-7 C20H26O5
DaMMarenediol II 3-O-caffeate DaMMarenediol II 3-O-caffeate 171438-55-4 C39H58O5
ent-3β-Hydroxykaur-16-en-19-oic acid ent-3β-Hydroxykaur-16-en-19-oic acid 66556-91-0 C20H30O3
Pterisolic acid E Pterisolic acid E 1401419-89-3 C20H30O5
3,5,7,15-Tetraacetoxy-9-
nicotinoyloxy-6(17),11-jatrophadien-14-one 3,5,7,15-Tetraacetoxy-9- nicotinoyloxy-6(17),11-jatrophadien-14-one 244277-75-6 C34H43NO11
GeloMulide N GeloMulide N 1005212-02-1 C24H32O7
Glutinol acetate Glutinol acetate 6426-44-4 C32H52O2
2-Acetoxy-3-deacetoxycaesaldekarin E 2-Acetoxy-3-deacetoxycaesaldekarin E 18326-06-2 C24H30O6
6-O-Nicotinoylscutebarbatine G 6-O-Nicotinoylscutebarbatine G 1206805-30-2 C32H36N2O8
9-Deacetyl-9-benzoyl-
10-debenzoyl-4β,20-epoxytaxchinin A 9-Deacetyl-9-benzoyl- 10-debenzoyl-4β,20-epoxytaxchinin A 227011-48-5 C31H40O11
ent-7α,9-Dihydroxy-
15-oxokaur-16-en-19,6β-olide ent-7α,9-Dihydroxy- 15-oxokaur-16-en-19,6β-olide 59885-89-1 C20H26O5
Neocaesalpin L Neocaesalpin L 952473-86-8 C26H36O11
Norcaesalpinin E Norcaesalpinin E 854038-96-3 C21H28O6
(1R,4aS,10aR)-7-Acetyl-1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-9-oxo-1-phenanthrenecarboxylic acid (1R,4aS,10aR)-7-Acetyl-1,2,3,4,4a,9,10,10a-octahydro-1,4a-dimethyl-9-oxo-1-phenanthrenecarboxylic acid 120591-53-9 C19H22O4
14beta-Benzoyloxy-2-deacetylbaccatin VI 14beta-Benzoyloxy-2-deacetylbaccatin VI 705973-69-9 C37H46O15
18-rabieta-8,11,13-triene-4,15-diol 18-rabieta-8,11,13-triene-4,15-diol 203455-81-6 C19H28O2
9,13-Epidioxy-8(14)-abieten-18-oic acid 9,13-Epidioxy-8(14)-abieten-18-oic acid 5309-35-3 C20H30O4
Abieta-8,11,13-triene-7,15,18-triol Abieta-8,11,13-triene-7,15,18-triol 337527-10-3 C20H30O3
Epieriocalyxin A Epieriocalyxin A 191545-24-1 C20H24O5
Karavilagenin D Karavilagenin D 934739-29-4 C30H46O4
Methyl 7,15-dihydroxydehydroabietate Methyl 7,15-dihydroxydehydroabietate 155205-65-5 C21H30O4
Serratenediol diacetate Serratenediol diacetate 27832-84-4 C34H54O4
3-EpiMeliasenin B 3-EpiMeliasenin B 1222475-77-5 C30H44O4
Bisandrographolide C Bisandrographolide C 160498-02-2 C40H56O8
bryonolic acid bryonolic acid 24480-45-3 C30H48O3
8-debenzoylpaeoniflorin 8-debenzoylpaeoniflorin 23532-11-8 C16H24O10
palbinone palbinone 139954-00-0 C22H30O4
1-hydroxy-7,9-dideacetylbaccatin I 1-hydroxy-7,9-dideacetylbaccatin I 142203-64-3 C28H40O12
INGENOL-20-HEXADECANOATE INGENOL-20-HEXADECANOATE 39071-33-5 C36H58O6
Diosbulbin C Diosbulbin C 20086-07-1 C19H22O7
(4R)-10-Hydroxy-9α-methyl-20-norkaur-16-en-18-oic acid 18,10-lactone (4R)-10-Hydroxy-9α-methyl-20-norkaur-16-en-18-oic acid 18,10-lactone 73483-88-2 C20H28O2
1-(3-Methyl-2-furanyl)-3-methyl-2-buten-1-one 1-(3-Methyl-2-furanyl)-3-methyl-2-buten-1-one 6138-88-1 C10H12O2
13-Hydroxylabda-8(17),14-dien-18-oic acid 13-Hydroxylabda-8(17),14-dien-18-oic acid 83915-59-7 C20H32O3
Scutebata C Scutebata C 1207181-59-6 C28H35NO9
Tyromycic acid Tyromycic acid 865543-37-9 C30H44O3
14-Deoxy-12-hydroxyandrographolide 14-Deoxy-12-hydroxyandrographolide 219721-33-2 C20H30O5
3α-CinnaMoyloxypterokaurene L3 3α-CinnaMoyloxypterokaurene L3 79406-13-6 C29H36O5
Methyl dodovisate A Methyl dodovisate A 1246937-33-6 C21H26O3
Scutebarbatine Y Scutebarbatine Y 1312716-27-0 C33H35NO7
16-Deoxysaikogenin F 16-Deoxysaikogenin F 57475-62-4 C30H48O3
3α-Acetoxy-20-oxo
-29-norlupane-23,28-dioic acid 3α-Acetoxy-20-oxo -29-norlupane-23,28-dioic acid 262272-76-4 C31H46O7
Lup-20(29)-ene-3β,23-diol Lup-20(29)-ene-3β,23-diol 163060-07-9 C30H50O2
XYLOTAXOL B, 7-(P) XYLOTAXOL B, 7-(P) 90352-19-5 C50H61NO18
Pterisolic acid C Pterisolic acid C 1401419-87-1 C20H26O4
GeloMulide B GeloMulide B 122537-60-4 C22H28O6
Yucalexin P-17 Yucalexin P-17 119642-82-9 C20H30O3
Aphadilactone C Aphadilactone C 1522004-70-1 C40H52O8
Jatrophane 1 Jatrophane 1 210108-85-3 C36H45NO13
Mudanpioside J Mudanpioside J 262350-52-7 C31H34O14
2-oxopomolic acid 2-oxopomolic acid 54963-52-9 C30H46O5
21-EPISERRATENEDIOL 21-EPISERRATENEDIOL 1449-06-5 C30H50O2
21-Episerratriol 21-Episerratriol 24513-57-3 C30H50O3
9-Deacetyl-9-benzoyl-10-debenzoyltaxchinin A 9-Deacetyl-9-benzoyl-10-debenzoyltaxchinin A 172486-22-5 C31H40O10
Epitulipinolide diepoxide Epitulipinolide diepoxide 39815-40-2 C17H22O6
(3aR,6S,7aR)-3a,6,7,7a-Tetrahydro-6-hydroxy-6-methyl-3-methylene-2,5(3H,4H)-benzofurandione (3aR,6S,7aR)-3a,6,7,7a-Tetrahydro-6-hydroxy-6-methyl-3-methylene-2,5(3H,4H)-benzofurandione 98751-78-1 C10H12O4
15-Oxo-9-hydroxykaur-16-en-18-oic acid 15-Oxo-9-hydroxykaur-16-en-18-oic acid 77658-39-0 C20H28O4
11α,12α-Epoxy-13α-methyl-27-noroleana-14-ene-3β-ol acetate 11α,12α-Epoxy-13α-methyl-27-noroleana-14-ene-3β-ol acetate 2111-46-8 C32H50O3
[2S,(-)]-2β-(3-Furanyl)-6β-(β-D-glucopyranosyloxy)-1,4,4aα,5,6,6a,9,10,10aα,10b-decahydro-9α-hydroxy-6aα,10bβ-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester [2S,(-)]-2β-(3-Furanyl)-6β-(β-D-glucopyranosyloxy)-1,4,4aα,5,6,6a,9,10,10aα,10b-decahydro-9α-hydroxy-6aα,10bβ-dimethyl-4-oxo-2H-naphtho[2,1-c]pyran-7-carboxylic acid methyl ester 104901-05-5 C27H36O12
Ent-16S,17-dihydroxyatisan-3-one Ent-16S,17-dihydroxyatisan-3-one 112523-91-8 C20H32O3
5,19-Epoxy-19,25-
dimethoxycucurbita-6,23-dien-3-ol 5,19-Epoxy-19,25- dimethoxycucurbita-6,23-dien-3-ol 85372-72-1 C32H52O4
Email:[email protected] [email protected]
Copyright © 2024 Mywellwork.com All rights reserved.