3856-25-5

Basic information

• Product Name: (-)-ALPHA-COPAENE
• Synonyms: (-)-ALPHA-COPAENE;Aglaiene;Copaen;Copaene;Tricyclo[4.4.0.0(2,7)]dec-3-ene, 1,3-dimethyl-8-(1-methylethyl)-, st;Tricyclo[4.4.0.0(2,7)]dec-3-ene, 8-isopropyl-1,3-dimethyl-;Tricyclo[4.4.0.02,7]dec-3-ene, 1,3-dimethyl-8-(1-methylethyl)-, stereoisomer;Tricyclo[4.4.0.02,7]dec-3-ene, 8-isopropyl-1,3-dimethyl-, (1R,2S,6S,7S,8S)-(-)-
• CAS NO: 3856-25-5
• Molecular Formula: C15H24
• Molecular Weight: 204.35
• EINECS: 223-364-4
• Mol File: 3856-25-5.mol
• Article Data: 5

Chemical Properties

• Melting Point: 74 °C
• Boiling Point: 124 °C15 mm Hg(lit.)
• Flash Point: 105.1°C
• Appearance: /
• Density: 0.910 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.038mmHg at 25°C
• Refractive Index: n20/D 1.490
• Storage Temp.: −20°C
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: (-)-ALPHA-COPAENE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ALPHA-COPAENE(3856-25-5)
• EPA Substance Registry System: (-)-ALPHA-COPAENE(3856-25-5)

Safety Data

• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 3856-25-5(Hazardous Substances Data)

Usage

Description

(-)-ALPHA-COPAENE, also known as α-Copaene, is a sesquiterpene found in a variety of plants, including Cannabis and S. aethiopis. It is a tricyclic compound with antiproliferative and antioxidant properties. α-Copaene inhibits the proliferation of primary rat neurons, N2a rat neuroblastoma cells, and cultured human lymphocytes in a concentration-dependent manner. It also increases the total antioxidant capacity in these cells when used at specific concentrations. Structurally, it is a tricyclo[4.4.0.02,7]dec-3-ene bearing an isopropyl substituent at position 8 and two methyl substituents at positions 1 and 3 (the 1S,6S,7S,8S-isastereomer).

Uses

Used in Pharmaceutical Industry:
(-)-ALPHA-COPAENE is used as an antiproliferative agent for its ability to inhibit the proliferation of primary rat neurons, N2a rat neuroblastoma cells, and cultured human lymphocytes. This property makes it a potential candidate for the development of treatments targeting cancer and other proliferative disorders.
Used in Antioxidant Applications:
(-)-ALPHA-COPAENE is used as an antioxidant for its ability to increase the total antioxidant capacity in primary rat neurons, N2a neuroblastoma cells, and cultured human lymphocytes. This characteristic can be beneficial in the development of therapies aimed at combating oxidative stress-related conditions and promoting overall cellular health.
Used in Anti-plasmodial Applications:
(-)-ALPHA-COPAENE is used as an anti-plasmodial agent for its activity against P. falciparum in culture. This application highlights its potential use in the development of treatments for malaria and other plasmodium-related diseases.

Purification Methods

Purify it by distillation, preferably under vacuum. [Heathcock J Am Chem Soc 88 4110 1966, Heathcock et al. J Am Chem Soc 89 4133 1967, Corey & Watt J Am Chem Soc 95 2303 1973, Beilstein 5 IV 1189.]

InChI:InChI=1/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12-,13-,14+,15+/m0/s1

Synthetic route

(+)-copan-3-ol → (-)-α-muurolene (483-75-0, 13862-36-7, 17627-24-6, 20085-19-2, 23515-88-0, 24406-05-1, 31983-21-8, 51260-25-4, 68000-45-3, 82468-90-4, 31983-22-9, 10208-80-7) + γ-muurolene (24268-39-1) + delta-cadinene (483-76-1, 13061-82-0, 16729-01-4, 20085-20-5, 60305-17-1, 73365-79-4) + copaene (3856-25-5)

Conditions	Yield
With trifluoroacetic anhydride In dichloromethane for 0.5h; Inert atmosphere;

copaene (3856-25-5) → 4,10-dichloro-4βH,10βH-cadinane (16641-30-8)

Conditions	Yield
With hydrogenchloride In diethyl ether

copaene (3856-25-5) → ((1R:4S:6S:7S)-1-methyl-4-isopropenyl-7-acetyl-norpinanyl-(6))-acetic acid (890-68-6)

Conditions	Yield
(i) O3, AcOEt, (ii) H2O2, aq. Na2CO3; Multistep reaction;

copaene (3856-25-5) → α-Copaen-15-al (182508-80-1)

Conditions	Yield
With selenium(IV) oxide

copaene (3856-25-5) → (1R,4aS,5R,8S,8aS)-8-Isopropyl-2,5-dimethyl-decahydro-1,5-cyclo-naphthalene-2,3-diol

Conditions	Yield
(i) OsO4, Py, Et2O, (ii) mannitol, aq. KOH; Multistep reaction;

copaene (3856-25-5) → Copaensaeure

Conditions	Yield
With dipyridine chromium trioxide In dichloromethane

copaene (3856-25-5) → Dihydrocopaen

Conditions	Yield
With hydrogen; platinum(IV) oxide In acetic acid

copaene (3856-25-5) → (1S,4aS,5S,8S,8aR)-8-Isopropyl-4,5-dimethyl-4a,5,6,7,8,8a-hexahydro-1H-1,5-cyclo-naphthalen-2-one

Conditions	Yield
With chromium(VI) oxide; acetic acid; tert-butyl alcohol In benzene Ambient temperature;

copaene (3856-25-5) → ((1R,4S,5S,6S,7S)-7-Acetyl-4-isopropyl-1-methyl-bicyclo[3.1.1]hept-6-yl)-acetic acid

Conditions	Yield
(i) O3, AcOEt, (ii) aq. H2O2, AcOH; Multistep reaction;

copaene (3856-25-5) → Copaendiol

Conditions	Yield
With pyridine; osmium(VIII) oxide

copaene (3856-25-5) → Epicopaon

Conditions	Yield
With sodium methylate

copaene (3856-25-5) → α-Copaen-15-ol (115728-41-1) + α-Copaen-15-al (182508-80-1)

Conditions	Yield
With selenium(IV) oxide In ethanol for 32h; Heating; Yield given. Yields of byproduct given;

copaene (3856-25-5) → β‐copaene (317819-78-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: SeO2 2: N2H4, KOH / bis-(2-hydroxy-ethyl) ether View Scheme

copaene (3856-25-5) → (1S,4aR,5R,8S,8aS)-8-Isopropyl-5-methyl-octahydro-1,5-cyclo-naphthalen-4-one

Conditions	Yield
Multi-step reaction with 3 steps 1: SeO2 2: N2H4, KOH / bis-(2-hydroxy-ethyl) ether 3: O3 View Scheme

copaene (3856-25-5) → Copaen-ketol

Conditions	Yield
Multi-step reaction with 2 steps 1: OsO4, Py 2: CrO3, Py View Scheme

Upstream product

• 137918-00-4 7(R*)-bromo-1-methyl-4(S*)-isopropyl-6(R*)-<1(R*)-(p-tolylsulfonyl)-4-(trimethylsilyl)-3-butynyl>bicyclo<3.1.1>heptan-6-ol 
• 137917-99-8 7(R*)-chloro-1-methyl-4(S*)-isopropyl-6(R*)-<1(R*)-(p-tolylsulfonyl)-4-(trimethylsilyl)-3-butynyl>bicyclo<3.1.1>heptan-6-ol 
• 137917-99-8 7(R*)-chloro-1-methyl-4(S*)-isopropyl-6(R*)-<1-(p-tolylsulfonyl)-4-(trimethylsilyl)-3-butynyl>bicyclo<3.1.1>heptan-6-ol 
• 137918-09-3 6-hydroxy-5(R*)-(p-tolylsulfonyl)-β-copaene vinylsilane 
• 137918-11-7 7(R*)-bromo-1-methyl-4(S*)-isopropyl-6(R*)-<1(R*)-(p-tolylsulfonyl)-3-butynyl>bicyclo<3.1.1>heptan-6-ol 
• 137918-07-1 6-hydroxy-5(R*)-(p-tolylsulfonyl)-β-copaene 
• 137918-13-9 6-acetoxy-β-copaene 
• 137918-04-8 7(R*)-chloro-1-methyl-4(S*)-isopropyl-6(R*)-<4-(trimethylsilyl)-3-butynyl>bicyclo<3.1.1>heptan-6-ol 
• 137918-06-0 6-hydroxy-β-copaene 
• 105453-16-5 germacrene D 
• 18252-44-3 (+/-)-β-copaene 
• 13567-74-3 copan-3-ol 
• 40716-68-5 (2-cis,6-trans)-farnesyl diphosphate 

Downstream Products

• 22415-05-0 isosativene 
• 483-75-0 (-)-α-muurolene 
• 6617-49-8 calamenene 
• 483-76-1 delta-cadinene 
• 41702-63-0 (+)-10-epi-zonarene 

Relevant articles and documents

Alternate Cyclization Cascade Initiated by Substrate Isomer in Multiproduct Terpene Synthase from Medicago truncatula

Promiscuity of terpene synthases results in the enormous diversity of terpenes found in nature. Multiproduct sesquiterpene synthase MtTPS5 isolated from Medicago truncatula generates 27 optically pure products from its natural substrate (2E,6E)-farnesyl diphosphate (FDP). In order to study the promiscuity of MtTPS5, (2Z,6E)-FDP, an analogue of presumptive reaction intermediates from natural reaction cascade, was utilized as a substrate. This stereoisomer induced a novel cyclization pathway leading to sesquiterpenes based on humulane, amorphene, and himachalane skeletons. Interestingly, none of these products matched those observed on incubation of MtTPS5 with natural (2E,6E)-FDP. Further determination of the absolute configuration of each product helped rebuild the stereochemical route of the reaction cascade. Interestingly, the presence of only one enantiomer of each product was observed, indicating the highly stereospecific nature of the enzymatic reaction. Substrate promiscuity of terpene synthases provides organism access to novel chemical bouquets of high optical purity by utilizing existing enzymes. The presence of this mechanism was indicated by the presence of these alternate products in natural herbivore-induced volatiles of M. truncatula.

The role of germacrene D as a precursor in sesquiterpene biosynthesis: Investigations of acid catalyzed, photochemically and thermally induced rearrangements

Germacrene D is considered as a precursor of many sesquiterpene hydrocarbons. We have investigated the acid catalyzed as well as the photochemically and thermally induced rearrangement processes of germacrene D isolated from several Solidago species, which contain both enantiomers of germacrene D. Enantiomeric mixtures of sesquiterpenes of the cadinane, eudesmane (selinane), oppositane, axane, isodaucane, and bourbonane group as well as isogermacrene D were identified as main products and made available as reference compounds for structure investigations and stereochemical assignments of plant constituents. δ-Amorphene, one of the rearrangement products, was identified as a natural product for the first time. The absolute configuration of γ-amorphene was revised by correlation with the absolute configuration of germacrene D. The mechanisms of the rearrangement reactions are discussed. (C) 2000 Elsevier Science Ltd.

SESQUITERPENE ALCOHOLS OF THE COPANE SERIES FROM ESSENTIAL OIL OF OCIMUM AMERICANUM

The volatile oil of Ocimum americanum afforded nine monoterpene hydrocarbons, four oxygenated monoterpenes, 12 sesquiterpene hydrocarbons, 7 sesquiterpene alcohols and a few unidentified trace compounds.Four new alcohols of the uncommon copane series have also been isolated and their structures elucidated by spectroscopic methods and chemical transformations.