cis-Jasmone

Compound Structure:

Synonyms:

cis-Jasmone;JASMONE;488-10-8;(Z)-Jasmone;cis-?Jasmone;FEMA No. 3196;(Z)-3-Methyl-2-(pent-2-en-1-yl)cyclopent-2-enone;cis-3-Methyl-2-(2-pentenyl)-2-cyclopenten-1-one;2-Cyclopenten-1-one, 3-methyl-2-(2-pentenyl)-, (Z)-;3-Methyl-2-pent-2-enylcyclopent-2-enon

Compound ID:

NMPC-765

PubChem ID:

1549018

Molecular Formula:

C11H16O

Canonical SMILES:

CCC=CCC1=C(CCC1=O)C

InChIKey:

XMLSXPIVAXONDL-PLNGDYQASA-N

About the compound:

Jasmone is an organic compound and a volatile element of jasmine flower oil. It appears as a colorless to pale yellow liquid and exists in two isomeric forms, distinguished by the geometry around their pentenyl double bond: cis-jasmone and trans-jasmone. In natural extracts, only the cis form is present, while synthetic variants often contain a mix of both, with the cis form being more predominant. Despite their structural differences, both forms of jasmone share similar odors and chemical properties. The structure of jasmone was first deduced by the scientist Lavoslav Ružička. In plants, jasmone is synthesized through the metabolism of jasmonic acid, involving a decarboxylation process. This compound plays a dual role in nature, acting as either an attractant or a repellent for various insects. In commercial applications, jasmone is predominantly used in the perfume and cosmetics industries due to its appealing fragrance.

GHS Hazard Statements

• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

• H319 (99.63%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

• H335 (74.17%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Properties:

Chemical and Physical Properties

Computed Properties

Property Name	Property Value
Molecular Weight	164.24 g/mol
XLogP3-AA	2.2
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	3
Exact Mass	164.120115130 g/mol
Monoisotopic Mass	164.120115130 g/mol
Topological Polar Surface Area	17.1Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	233
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes
Physical Description	Liquid, Pale yellowish to straw-coloured oily liquid; odour of jasmine
Boiling Point	285 °C
Density	0.9437 g/cu cm at 22 °C
Solubility	Soluble in ethanol, ether, carbon tetrachloride, lignin

Source: PubChem

Source Species:

Eucalyptus torelliana

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