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Jasmone information


Jasmone
Ball-and-stick model of jasmone
Names
Preferred IUPAC name
3-methyl-2-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-one
Other names
cis-Jasmone
Identifiers
CAS Number
  • 488-10-8 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
ChemSpider
  • 1266012 ☒N
PubChem CID
  • 1549018
UNII
  • RC4W0G9YUK checkY
InChI
  • InChI=1S/C11H16O/c1-3-4-5-6-10-9(2)7-8-11(10)12/h4-5H,3,6-8H2,1-2H3/b5-4- ☒N
    Key: XMLSXPIVAXONDL-PLNGDYQASA-N ☒N
SMILES
  • CC\C=C/CC1=C(CCC1=O)C
  • O=C1\C(=C(/CC1)C)C\C=C/CC
Properties
Chemical formula
C11H16O
Molar mass 164.246 g/mol
Appearance colorless to pale yellow liquid
Density 0.94 g/mL, liquid
Melting point 203 to 205 °C (397 to 401 °F; 476 to 478 K)
Boiling point 146 °C (295 °F; 419 K) at 27 mmHg
Solubility in water
in water
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Jasmone is an organic compound, which is a volatile portion of the oil from jasmine flowers. It is a colorless to pale yellow liquid. Jasmone can exist in two isomeric forms with differing geometry around the pentenyl double bond, cis-jasmone and trans-jasmone. The natural extract contains only the cis form, while synthetic material is often a mixture of both, with the cis form predominating. Both forms have similar odors and chemical properties. Its structure was deduced by Lavoslav Ružička.[1]

Jasmone is produced by some plants by the metabolism of jasmonic acid, via a decarboxylation.[2] It can act as either an attractant or a repellent for various insects. Commercially, jasmone is used primarily in perfumes and cosmetics.

  1. ^ Ruzicka, L.; Pfeiffer, M. (1933). "Über Jasminriechstoffe I. Die Konstitution des Jasmons" [On Jasmine Perfumes I. The Composition of Jasmone]. Helvetica Chimica Acta. 16: 1208–1214. doi:10.1002/hlca.193301601153.
  2. ^ Dąbrowska, P.; Boland, W. (2007). "iso-OPDA: An Early Precursor of cis-Jasmone in Plants?". ChemBioChem. 8: 2281–2285. doi:10.1002/cbic.200700464.

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Jasmone

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Jasmone is an organic compound, which is a volatile portion of the oil from jasmine flowers. It is a colorless to pale yellow liquid. Jasmone can exist...

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Cyclopentanone

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common precursor to fragrances, especially those related to jasmine and jasmone. Examples include 2-pentyl- and 2-heptylcyclopentanone. It is a versatile...

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Bombyx mori

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preference for white mulberry, having an attraction to the mulberry odorant cis-jasmone. They are not monophagous, since they can eat other species of Morus, as...

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C11H16O

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The molecular formula C11H16O may refer to: Jasmone Various aromatic alcohols with one benzene ring Various aromatic ethers such as benzyl tert-butyl...

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Aroma compound

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woody Violet Thujone Minty Wormwood, lilac, juniper Eucalyptol Eucalyptus Eucalyptus Jasmone spicy, fruity, floral in dilution Jasmine, Honeysuckle...

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Nazarov cyclization reaction

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ubiquity of cyclopentenones as both motifs in natural products (including jasmone, the aflatoxins, and a subclass of prostaglandins) and as useful synthetic...

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Cyclopentenone

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Cyclopentenones are found in a large number of natural products, including jasmone, the aflatoxins, and several prostaglandins. 2-Cyclopentenones can be synthesized...

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Cereal leaf beetle

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; Lemanczyk, G.; Wrzesinska, D.; Piesik, D. (May 2013). "Synthetic cis-jasmone exposure induces wheat and barley volatiles that repel the pest cereal...

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Jasmonic acid

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some biological contexts. Decarboxylation affords the related fragrance jasmone. Demole, E.; Lederer, E.; Mercier, D. (1962). "Isolement et determination...

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Jasmonate

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nigrum's herbivore resistance. JA undergoes decarboxylation to give cis-jasmone. Although jasmonate (JA) regulates many different processes in the plant...

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Nikolay Zefirov

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anhydride. Later these transformations have found applications for the trans-Jasmone synthesis. It is noteworthy that all research work of this time was conducted...

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Jasmine in Karnataka

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from 0.24 to 0.42 per cent. The principal aromatic components are Indol, Jasmone, Benzyl Acetate, Benzyl Benzoate, Methyl Anthranilate, Linalool & Geraniol...

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Floral scent

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2009). "Attraction of New Zealand Flower Thrips, Thrips obscuratus, to cis-Jasmone, a Volatile Identified from Japanese Honeysuckle Flowers". Journal of Chemical...

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