6-Methyl-5-Hepten-2-one (Sulcatone)

6-Methyl-5-Hepten-2-one (Sulcatone)
Compound Structure:
Synonyms: 6-METHYL-5-HEPTEN-2-ONE;110-93-0;Sulcatone;2-Methyl-2-hepten-6-one;5-HEPTEN-2-ONE, 6-METHYL-;METHYL HEPTENONE;6-Methyl-5-heptene-2-one;2-Oxo-6-methylhept-5-ene;Heptenone, methyl-;2-Methyl-6-oxo-2-heptene;prenylacetone
Compound ID: NMPC-474
PubChem ID:

9862

Molecular Formula: C8H14O
Canonical SMILES: CC(=CCCC(=O)C)C
InChIKey: UHEPJGULSIKKTP-UHFFFAOYSA-N
About the compound:

Sulcatone, known in the scientific community as 6-Methyl-5-hepten-2-one, is distinguished by its citrusy, fruity scent and is a colorless liquid resembling water in appearance. Its formula is C8H14O. This methylated ketone is notably effective as an attractant for the Aedes aegypti mosquito, which possesses an odor receptor gene (Or4) specifically sensitive to sulcatone. This trait renders it particularly valuable for research aimed at vector control and mitigating the spread of mosquito-transmitted diseases[1]. Studies have also shed light on sulcatone's importance in mosquitoes' selection of egg-laying sites. It has been identified as one of the semiochemicals critical for directing mosquitoes to preferred oviposition environments. This insight suggests the possibility of employing such compounds to devise methods for controlling mosquito populations by influencing their reproductive behaviors. Sulcatone, together with other molecules like β-caryophyllene, decanal, and limonene, has been found to provoke antenna responses in mosquitoes during gas chromatography-electroantennographic detection (GC-EAD) studies, showcasing its pivotal influence on mosquito activity[2]. Additionally, research into sulcatone has extended to its application in bioinsecticide development, targeting pests such as Spodoptera littoralis. These investigations reveal sulcatone's wider potential in pest management and control strategies, presenting an eco-friendlier alternative to conventional chemical insecticides[3].

References 

1. Wikipedia contributors. "Sulcatone." Wikipedia, The Free Encyclopedia. Last modified May 2, 2021. https://en.wikipedia.org/wiki/Sulcatone. 

2. Okumu, Fredros O., et al. "Controlling mosquitoes with semiochemicals: a review." Parasites & Vectors, vol. 13, no. 1, 2020. https://parasitesandvectors.biomedcentral.com/articles/10.1186/s13071-019-3495-3. 

3. Vasileiadis, S., et al. "Fermentation as an Alternative Process for the Development of Bioinsecticides." Fermentation, vol. 5, no. 3, 2019. https://www.mdpi.com/2311-5637/5/3/58. 

GHS Hazard Statements

H226 (100%): Flammable liquid and vapor [Warning Flammable liquids]

H319 (77.33%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

126.20 g/mol

XLogP3

1.9

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

3

Exact Mass

126.104465066 g/mol

Monoisotopic Mass

126.104465066 g/mol

Topological Polar Surface Area

17.1Ų

Heavy Atom Count

9

Formal Charge

0

Complexity

119

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Colourless slightly yellow liquid; strong fatty, green citrus-like odour

Boiling Point

72.00 to 73.00 °C. @ 18.00 mm Hg

Meting Point

-67 °C

Density

0.846-0.854

Solubility 

Insoluble in water; soluble in oils and organic solvents

Vapor Pressure

0.75 [mmHg]

 

Source: PubChem

Source Species: Cymbopogon citratus
Hirsute Palisota
Pteris togoensis
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