Citral
| Skeletal formula of geranial Geranial
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| Ball-and-stick model of the geranial molecule | |
| Skeletal formula of neral Neral
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| Ball-and-stick model of the neral molecule | |
| Names | |
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| IUPAC name
3,7-dimethylocta-2,6-dienal
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| Other names
citral
geranialdehyde |
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| Identifiers | |
5392-40-5  |
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| ChEBI | CHEBI:16980 |
| ChEMBL | ChEMBL1080997 |
| ChemSpider | 553578 |
| 6327 | |
| Jmol 3D model | Interactive image Interactive image |
| KEGG | C01499 |
| PubChem | 638011 |
| RTECS number | RG5075000 |
| UNII | T7EU0O9VPP |
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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) |
| Vapor pressure | {{{value}}} |
| Related compounds | |
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Related alkenals
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Citronellal |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
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.
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, 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
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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
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Lua error in package.lua at line 80: module 'strict' not found.
- ↑ Survey and health assessment of chemical substances in massage oils
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