Citral
Citral[1] | |
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IUPAC name 3,7-dimethylocta-2,6-dienal | |
Other names citral | |
Identifiers | |
CAS number | 5392-40-5 |
PubChem | 638011 |
ChemSpider | 553578 |
UNII | T7EU0O9VPP |
KEGG | C01499 |
ChEBI | CHEBI:16980 |
ChEMBL | CHEMBL1080997 |
RTECS number | RG5075000 |
Jmol-3D images | Image 1 Image 2 |
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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; 444 °F; 502 K |
Vapor pressure | 0.22 mmHg (20 °C) |
Hazards | |
R-phrases | R36, R37, R38 |
NFPA 704 |
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Flash point | 91 °C; 196 °F; 364 K |
Related compounds | |
Related alkenals | Citronellal |
(verify) (what is: / ?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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.
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
Two studies have shown 1-1.7% of people to be allergic to citral, and allergies are frequently reported. Citral on its own is strongly sensitizing to allergies; the International Fragrance Association recommends that citral only be used in association with substances that prevent a sensitizing effect. Citral has been extensively tested and has no known genotoxicity, and no known carcinogenic effect, but animal tests show dose-dependent effects on the kidneys.[8]
Compendial status
See also
- Limonene
- Citronellal
- Geraniol
- Nerol
- Vaporizer
References
- ↑ Citral, The Merck Index, 12th Edition.
- ↑ Fenaroli, G., Furia, T.E., Bellanca, N., Handbook of Flavor Ingredients, ISBN 0-87819-532-7
- ↑ Lawless, J., The Illustrated Encyclopedia of Essential Oils, ISBN 1-85230-661-0
- ↑ The Aromatic Plant Project
- ↑ 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.
- ↑ 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.
- ↑ 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.
- ↑ Survey and health assessment of chemical substances in massage oils
- ↑ The British Pharmacopoeia Secretariat (2009). "Index, BP 2009". Retrieved 31 March 2010.