Citral: Difference between revisions
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== Compendial status == |
== Compendial status == |
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* [[British Pharmacopoeia]]<ref name=ib29>{{cite web |
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Revision as of 08:24, 25 November 2016
Geranial
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Neral
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Names | |
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IUPAC name
3,7-dimethylocta-2,6-dienal
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Other names
citral
geranialdehyde | |
Identifiers | |
3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.023.994 |
KEGG | |
PubChem CID
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RTECS number |
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UNII | |
CompTox Dashboard (EPA)
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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) |
Vapor pressure | 0.22 mmHg (20 °C) |
Hazards | |
NFPA 704 (fire diamond) | |
Flash point | 91 °C (196 °F; 364 K) |
Related compounds | |
Related alkenals
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Citronellal |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Citral, or 3,7-dimethyl-2,6-octadienal or lemonal, is either a pair, or a mixture 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, 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
This section needs expansion. You can help by adding to it. (March 2010) |
See also
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.
{{cite journal}}
: CS1 maint: multiple names: authors list (link) - ^ 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" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 31 March 2010.
{{cite web}}
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External links