Geranylacetone

Geranylacetone
Compound Structure:
Synonyms: Geranylacetone; Geranyl acetone; (5E)-6,10-dimethylundeca-5,9-dien-2-one; Dihydropseudoionone; (E)-6,10-Dimethylundeca-5,9-dien-2-one;trans-Geranylacetone;5,9-Undecadien-2-one, 6,10-dimethyl-;(E)-6,10-Dimethyl-5,9-undecadien-2-one
Compound ID: NMPC-042
PubChem ID:

1549778

Molecular Formula: C13H22O
Canonical SMILES: CC(=CCCC(=CCCC(=O)C)C)C
InChIKey: HNZUNIKWNYHEJJ-FMIVXFBMSA-N
About the compound:

Geranylacetone is a colorless oil formed by combining geranyl and acetonyl groups. This compound serves as a precursor for synthetic squalene. Geranylacetone can be synthesized through the transesterification of ethyl acetoacetate with linalool, or through esterification of linalool with ketene or isopropenyl methyl ether, followed by a Carroll rearrangement to yield geranylacetone. Geranylacetone plays a significant role in the production of isophytol, which is used in the manufacturing of Vitamin E. It also gives rise to other derivatives such as farnesol and nerolidol. This compound is a flavor component found in various plants, including rice, mango, and tomatoes. It is generated during the degradation of plant matter by ozone.In terms of its chemical structure, geranylacetone is a monoterpene ketone, featuring an (E)-geranyl group bonded to one of the alpha-methyls of acetone. It is present in essential oils from different plants, including Nelumbo nucifera. Geranylacetone serves as a flavoring agent, a fragrance, a component of volatile oils, and a plant metabolite. It contains a geranyl group. Furthermore, Geranylacetone is a natural product found in organisms like Lonicera japonica and Monteverdia ilicifolia. It is also a metabolite produced by Saccharomyces cerevisiae.

https://en.wikipedia.org/wiki/Geranylacetone

GHS Hazard Statements

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

H411 (99.94%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

194.31 g/mol

XLogP3-AA

3.7

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

6

Exact Mass

194.167065321 g/mol

Monoisotopic Mass

194.167065321 g/mol

Topological Polar Surface Area

17.1²

Heavy Atom Count

14

Formal Charge

0

Complexity

230

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

Clear colorless liquid; [Sigma-Aldrich MSDS]

Boiling Point

126–8 °C (259–46 °F; 399–281 K) 10 mm Hg

Density

0.861-0.873

Solubility 

slightly soluble in water; soluble in oil

Vapor Pressure

 

Source: PubChem

Source Species: Crateva adansonii
Klainedoxa gabonensis
Pachira glabra
Phyllanthus muellerianus
Vitex doniana
Cymbopogon citratus
Hirsute Palisota
Hyparrhenia rufa
Tagetes erecta
Acalypha segetalis
Eucalyptus torelliana
Pyrenacantha staudtii
Tecoma stans
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