Copaene

Copaene
Compound Structure:
Synonyms: Copaene;ALPHA-COPAENE;3856-25-5;.alpha.-Copaene;(-)-alpha-Copaene;[1S,2R,6R,7R,8S,(+)]-1,3-Dimethyl-8-(1-methylethyl)tricyclo[4.4.0.02,7]deca-3-ene;ylangene (alpha-);8-Isopropyl-1,3-dimethyltricyclo(4.4.0.02,7)dec-3-ene
Compound ID: NMPC-552
PubChem ID:

19725

Molecular Formula: C15H24
Canonical SMILES: CC1=CCC2C3C1C2(CCC3C(C)C)C
InChIKey: VLXDPFLIRFYIME-UHFFFAOYSA-N
About the compound:

Copaene, also known as α-copaene, is a naturally occurring compound present in plants like Curcuma amada and Pterodon emarginatus, among others, for which data is accessible. It's an oily liquid hydrocarbon commonly found in various essential oil-producing plants. The term "copaene" originates from the resin-producing tropical copaiba tree, Copaifera langsdorffii, from which it was first isolated in 1914. Its structure, along with its chirality, was determined in 1963. Another form, β-copaene, with a double-bond isomer containing an exocyclic-methylene group, was identified in 1967. Chemically, copaenes belong to the category of tricyclic sesquiterpenes. These molecules exhibit chirality, with the α-copaene enantiomer typically found in higher plants displaying a negative optical rotation of approximately -6°. Occasionally, the rare (+)-α-copaene is detected in small quantities in certain plants. The presence of (+)-α-copaene is noteworthy due to its strong attraction to an agricultural pest, the Mediterranean fruit fly Ceratitis capitata.

GHS Hazard Statements

H226 (50%): Flammable liquid and vapor [Warning Flammable liquids]

H304 (50%): May be fatal if swallowed and enters airways [Danger Aspiration hazard]

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]


Properties:

Chemical and Physical Properties

Computed Properties

Property Name

Property Value

Molecular Weight

204.35 g/mol

XLogP3-AA

4.5

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

0

Rotatable Bond Count

1

Exact Mass

204.187800766 g/mol

Monoisotopic Mass

204.187800766 g/mol

Topological Polar Surface Area

0Ų

Heavy Atom Count

15

Formal Charge

0

Complexity

312

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

5

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Source Species: Monodora myristica
Piper guineense
Tithonia rotundifolia
Cyperus articulatus
Murraya Koenigii
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