Citral


Citral
Citral[1]
Identifiers
CAS number 5392-40-5 YesY
PubChem 638011
ChemSpider 553578 YesY
UNII T7EU0O9VPP YesY
KEGG C01499 YesY
ChEBI CHEBI:16980 YesY
ChEMBL CHEMBL1080997 YesY
RTECS number RG5075000
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C10H16O
Molar mass 152.24 g/mol
Appearance Pale yellow liquid
Odor Lemon like
Density 0.893 g/cm³
Boiling point

229 °C, 502 K, 444 °F

Hazards
R-phrases R36, R37, R38
NFPA 704
NFPA 704.svg
1
0
0
Flash point 91 °C
Related compounds
Related alkenals Citronellal

Methacrolein
trans-2-Methyl-2-butenal

 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

Contents

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's lemon odor 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 antimicrobial 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 allergies.[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 (3): 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. 
  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 (5): 563–577. doi:10.1007/BF00989077. 
  8. ^ Survey and health assessment of chemical substances in massage oils
  9. ^ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009". http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf. Retrieved 31 March 2010. 

External links


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Look at other dictionaries:

  • citral — ● citral nom masculin Dénomination courante d un aldéhyde monoterpénique que l on rencontre dans les essences de citron, de lemon grass et de verveine. (Outre son usage comme parfum de citron, le citral est employé pour la synthèse de l ionone,… …   Encyclopédie Universelle

  • Citrāl — (Geranial) C10H16O, ein Aldehyd, der sich im Zitronenöl, Lemongrasöl (70–80 Proz.), im Pomeranzenöl, im westindischen Limettöl, im Melissenöl, Bay und Pimentöl, im japanischen Pfefferöl, im Sassafrasblätteröl und im Öl von Eucalyptus Staigeriana… …   Meyers Großes Konversations-Lexikon

  • Citral — Citral, s. Riechstoffe, künstliche …   Lexikon der gesamten Technik

  • citral — cìtrāl m <G citrála> DEFINICIJA kem. terpenski aldehid, sastavni dio mnogih eteričnih ulja (limun, naranča i dr.) ETIMOLOGIJA lat. citrus ← grč. kítron: limun + al …   Hrvatski jezični portal

  • citral — [si′trəl] n. [ CITR(I) + AL(DEHYDE)] a liquid aldehyde, C9H15·CHO, with a pleasant odor, found in oil of lemon, oil of lime, etc. and used as a flavoring agent and in perfumes …   English World dictionary

  • Citral — Strukturformel links Geranial (Citral A), rechts Neral (Citral B) …   Deutsch Wikipedia

  • Citral — Citrals néral (haut) et géranial (bas) Général Nom IUPAC 3,7 diméthyl 2,6 octadiènal …   Wikipédia en Français

  • citral — /si treuhl/, n. Chem. a pale yellow, water insoluble, liquid aldehyde, C10H16O, having a strong lemonlike odor, consisting in natural form of two isomers (citral a or geranial and citral b or neral), usually obtained from the oils of lemon and… …   Universalium

  • Citral — Ci|t|ral [lat. citrus = Zitronenbaum (↑ Citronensäure) ↑ al], das; s; Syn.: 3,7 Dimethylocta 2,6 dien: nach Zitrone riechendes fl. Stereoisomerengemisch aus Geranial (trans oder (E) Citral, früher: C. a) u. Neral ( …   Universal-Lexikon

  • citral — ˈsi.ˌtral noun ( s) Etymology: International Scientific Vocabulary citr + al : an unsaturated liquid aldehyde C9H15CHO that has a strong lemon and verbena odor, is found in many essential oils (as lemon oil and citronella oil), is used in… …   Useful english dictionary


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