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cis-3-Hexenal

From Wikipedia, the free encyclopedia
(Redirected fromHexenal)
cis-3-Hexenal
Names
Preferred IUPAC name
(3Z)-Hex-3-enal
Other names
(Z)-Hex-3-enal
cis-3-Hexenal
Leaf aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard100.027.141Edit this at Wikidata
EC Number
  • 229-854-4
KEGG
UNII
  • InChI=1/C6H10O/c1-2-3-4-5-6-7/h3-4,6H,2,5H2,1H3/b4-3-
    Key: GXANMBISFKBPEX-ARJAWSKDBM
  • O=CC\C=C/CC
Properties
C6H10O
Molar mass98.145 g·mol−1
Density0.851 g/cm3
Boiling point126 °C (259 °F; 399 K)
Related compounds
Related alkenals
Acrolein

Crotonaldehyde
(E,E)-2,4-Decadienal

Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

cis-3-Hexenal, also known as(Z)-3-hexenal andleaf aldehyde, is anorganic compound with the formula CH3CH2CH=CHCH2CHO. It is classified as anunsaturatedaldehyde. It is a colorless liquid and anaroma compound with an intenseodor offreshly cut grass andleaves.[1][2]

Occurrence

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It is one of the major volatile compounds in ripetomatoes, although it tends toisomerize into theconjugatedtrans-2-hexenal.[3] It is produced in small amounts by mostplants and it acts as anattractant to manypredatoryinsects. It is also apheromone in many insect species.[4]

Biosynthesis of cis-3-hexenal fromlinolenic acid via the hydroperoxide by the action of a lipoxygenase followed by ahydroperoxide lyase.[5]

See also

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External links

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References

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  1. ^Cotton, Simon (2017)."Hexenal".Molecule of the Month. Chm.bris.ac.uk.doi:10.6084/m9.figshare.5245834. Retrieved2018-07-26.
  2. ^Hexenal / Chemistry World, Royal Society of Chemistry, 27 November 2013
  3. ^Buttery, Ron G.; Teranishi, Roy; Ling, Louisa C. (1987). "Fresh tomato aroma volatiles: A quantitative study".Journal of Agricultural and Food Chemistry.35 (4):540–544.doi:10.1021/jf00076a025.
  4. ^Ashraf El-Sayed."Pheromone database". Pherobase.com. Retrieved2018-07-26.
  5. ^KenjiMatsui (2006). "Green leaf volatiles: hydroperoxide lyase pathway of oxylipin metabolism".Current Opinion in Plant Biology.9 (3):274–280.Bibcode:2006COPB....9..274M.doi:10.1016/j.pbi.2006.03.002.PMID 16595187.
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