Pomarose

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Pomarose
Pomarose2D.svg
Pomarose3D.jpg
Names
Preferred IUPAC name
(2E,5Z)-5,6,7-Trimethylocta-2,5-dien-4-one
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C11H18O/c1-6-7-11(12)10(5)9(4)8(2)3/h6-8H,1-5H3/b7-6+,10-9- Yes check.svgY
    Key: QWRGOHMKGNCVAC-KQHSAVHASA-N Yes check.svgY
  • O=C(/C(C)=C(C)\C(C)C)/C=C/C
Properties
C11H18O
Molar mass 166.264 g·mol−1
Density 0.855 g/cm3
Boiling point 236.2 °C (457.2 °F; 509.3 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Pomarose is a high-impact captive odorant patented by Givaudan. [1] It is a double-unsaturated ketone that does not occur in nature. Pomarose has a powerful fruity rose odor with nuances of apples, plums and raisins, which is almost entirely due to the (2E,5Z)-stereoisomer, while its (2E,5E)-isomer is barely detectable for most people. [2] Catalyzed by traces of acids, both isomers equilibrate however quickly upon standing in glass containers.

Contents

Discovery and synthesis

5,6,7-Trimethylocta-2,5-dien-4-one was suspected by Philip Kraft et al. [3] by investigation of the NMR spectra of an unknown trace component with damascone odor in a crude complex reaction product. Although this trace component eventually turned out to be the constitutional isomer 2-methyl-3-isopropylhepta-2,5-dien-4-one. Pomarose was synthesized for structural curiosity and found to possess even superior fruity, rosy odor characteristics, reminiscent of apples, plums, raisins and other dried fruits with a low odor threshold of 0.5 ng/L air. The synthesis comprised borontrifluoride-catalyzed addition of methyl isopropyl ketone to 1-ethoxyprop-1-yne, which afforded ethyl 2,3,4-trimethylpent-2-enoate, and then was transformed into the target molecule by Grignard reaction with propen-1-ylmagnesium bromide via in situ enolization.

Use in perfumery

Pomarose has been used in a variety of perfumes. [4] It had its debut in Be Delicious for Men and it is also used in Unforgivable, 1 Million, CK free, Legend, Unforgivable Woman and John Galliano.

Related Research Articles

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Butanone Chemical compound

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Aldol condensation

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Aroma compound Chemical compound that has a smell or odor

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Cyclododecatriene Chemical compound

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Damascenone Chemical compound

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Philip Kraft

Philip Kraft is a German organic chemist. Since 1996 he has been employed by Givaudan, a leading Flavor and Fragrance company, where he designs captive odorants for use in perfumes. He has lectured at the University of Bern, the University of Zurich, and the ETH Zurich.

Rosefuran Chemical compound

Rosefuran (3-methyl-2-prenylfuran) is a liquid boiling at 103-104 °C, with a density of 0.9089 g/cm3, less than that of water. It is an aroma chemical which is a minor constituent of the aroma of the rose. Rosefuran is a 2,3-disubstituted furan. It has an odor threshold of 200 ppb and constitutes 0.16% of Bulgarian rose oil. Rosefuran has been established as a female sex pheromone of an acarid mite, Caloglyphus sp. Concentrations of less than 100 ng of synthetic rosefuran caused sexual excitation in males of the species.

Decenoic acid is any mono-carboxylic acid with an unbranched chain of ten carbons connected by eight single bonds and one double bond; that is, a chemical compound with formula HO(O=)C(CH
2
)
k
CH=CH(CH
2
)
7-k
–H, where k is between 0 and 7 inclusive.

2-(2-(4-Methyl-3-cyclohexen-1-yl)propyl)cyclopentanone Chemical compound

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References

  1. Kraft, Philip (2001). "Preparation of 2-,5-,6-,7-,8-substituted oct-2-en-4-ones with odor and taste properties". Eur. Pat. Appl. 2001: EP 1149820 A1 20011031.
  2. Swift, Karl, ed. (2002). Advances in flavours and fragrances: From the sensation to the synthesis. Cambridge: Royal Society of Chemistry. p. 138. ISBN   9780854048212.
  3. Kraft, Philip; Denis, Caroline; Eichenberger, Walter (2001). "5,6,7-Trimethylocta-2,5-dien-4-one − A Suspected Odorant with Surprising Olfactory Properties". European Journal of Organic Chemistry. 2001 (12): 2363–2369. doi:10.1002/1099-0690(200106)2001:12<2363::AID-EJOC2363>3.0.CO;2-E.
  4. Ohloff, Günther; Pickenhagen, Wilhelm; Kraft, Philip. (2012). Scent and Chemistry – The Molecular World of Odors. Zurich: Verlag Helvetica Chimica Acta. p. 217. ISBN   9783906390666.