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Citral

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Citral[1]
Geranial
Neral
Names
IUPAC name
3,7-dimethylocta-2,6-dienal
Other names
citral
geranial
neral
geranialdehyde
Identifiers
3D model (JSmol)
ECHA InfoCard 100.023.994 Edit this at Wikidata
RTECS number
  • RG5075000
  • O=CC=C(C)CCC=C(C)C
Properties
C10H16O
Molar mass 152.24 g/mol
Appearance Pale yellow liquid
Odor Lemon like
Density 0.893 g/cm³
Boiling point 229 °C (444 °F; 502 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0
1
0
Flash point 91 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Citral, or 3,7-dimethyl-2,6-octadienal or lemonal, is either of, or a mixture of, a pair of terpenoids with the molecular formula C10H16O. The two compounds are double bond isomers. The E-isomer is known as geranial or citral A. The Z-isomer is known as neral or citral B.

Occurrence

Citral is present in the oils of several plants, including lemon myrtle (90-98%), Litsea citrata (90%), Litsea cubeba (70-85%), lemongrass (65-85%), lemon tea-tree (70-80%), Ocimum gratissimum (66.5%), Lindera citriodora (about 65%), Calypranthes parriculata (about 62%), petitgrain (36%), lemon verbena (30-35%), lemon ironbark (26%), lemon balm (11%), lime (6-9%), lemon (2-5%), and orange.[2][3][4]

Uses

Geranial has a strong lemon odor. Neral has a lemon odor that is less intense, but sweeter. Citral is therefore an aroma compound used in perfumery for its citrus effect. Citral is also used as a flavor and for fortifying lemon oil. It also has strong anti-microbial qualities,[5] and pheromonal effects in insects.[6][7]

Citral is used in the synthesis of vitamin A, ionone, and methylionone, and to mask the smell of smoke.

Health and safety information

Citral should be avoided by people with perfume allergy.[8]

Compendial status

See also

References

  1. ^ Citral, The Merck Index, 12th Edition.
  2. ^ Fenaroli, G., Furia, T.E., Bellanca, N., Handbook of Flavor Ingredients, ISBN 0878195327
  3. ^ Lawless, J., The Illustrated Encyclopedia of Essential Oils, ISBN 1-85230-661-0
  4. ^ The Aromatic Plant Project
  5. ^ Onawunmi, G.O. (1989). "Evaluation of the antimicrobial activity of citral". Lett. Appl. Microbial. 9: 105–108. doi:10.1111/j.1472-765X.1989.tb00301.x.
  6. ^ Kuwahara, Y., Suzuki, H., Matsumoto, K. & Wada, Y. (1983). "Pheromone study on acarid mites. XI. Function of mite body as geometrical isomerization and reduction of citral (the alarm pheromone) Carpoglyphus lactis". Appl. Entomol. Zool. 18: 30–39.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ^ Robacker, D.C. & Hendry, L.B. (1977). "Neral and geranial: components of the sex pheromone of the parasitic wasp, Itoplectis conquisitor". J. Chem. Ecol. 3: 563–577. doi:10.1007/BF00989077.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  8. ^ Survey and health assessment of chemical substances in massage oils
  9. ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Retrieved 31 March 2010. {{cite web}}: Cite has empty unknown parameter: |coauthors= (help)

External links

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