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Citral

geranialdehyde | NFPA-H = 0 | NFPA-F = 1 | NFPA-R = 0 | NFPA-S = | Citronellal | Methacrolein | trans-2-Methyl-2-butenal

Citral is an acyclic monoterpene aldehyde. Being a monoterpene, it is made of two isoprene units. Citral is a collective term which covers two geometric isomers that have their own separate names; the E-isomer is named geranial (trans-citral; α-citral) or citral A. The Z-isomer is named neral (cis-citral; β-citral) or citral B. These stereoisomers occur as a mixture, often not in equal proportions; e.g. in essential oil of Australian ginger, the neral to geranial ratio is 0.61.

Natural Occurrence

Citral is present in the volatile oils of several plants:

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%)| orange

Of the many sources of citral, the Australian tree Backhousia citriodora (family Myrtaceae) is considered superior.

Uses

Citral is a precursor in the industrial production of vitamin A, vitamin E, vitamin K.

Citral is also precursor to lycopene, ionone and methylionone.

Fragrances

Citral has a strong lemon (citrus) scent and is used as an aroma compound in perfumery. It is used to fortify lemon oil. (Nerol, another perfumery compound, has a less intense but sweeter lemon note.) The aldehydes citronellal and citral are considered key components responsible for the lemon note with citral preferred.

It also has pheromonal effects in acari and insects.

The herb Cymbopogon citratus has shown promising insecticidal and antifungal activity against storage pests.

Food additive

Citral is commonly used as a food additive ingredient.

It has been tested (2016) in vitro against the food-borne pathogen Cronobacter sakazakii.

References

References

  1. '''Citral''', ''[[The Merck Index]]'', 12th Edition.
  2. (2020). "Lead Finding from Plant Cymbopogon Citratus with Immunomodulator Potentials through in Silico Methods". Chemistry Proceedings.
  3. (2008). "Chemistry of spices". CABI.
  4. "Handbook of Flavor Ingredients".
  5. (2 November 1995). "The Illustrated Encyclopedia of Essential Oils". Element.
  6. "The Aromatic Plant Project".
  7. (9 July 2021). "''Backhousia citriodora'' F. Muell. (Lemon Myrtle), an Unrivalled Source of Citral". Foods.
  8. (1983). "Pheromone Study on Acarid Mites. XI. Function of Mite Body as Geometrical Isomerization and Reduction of Citral (the Alarm Pheromone)". Applied Entomology and Zoology.
  9. (1977). "Neral and geranial: components of the sex pheromone of the parasitic wasp, Itoplectis conquisitor". Journal of Chemical Ecology.
  10. (1997). "Citral: A cytotoxic principle isolated from the essential oil of Cymbopogon citratus against P388 leukaemia cells". Current Science.
  11. (1 December 2015). "Anti-inflammatory activity of neral and geranial isolated from fruits of ''Litsea cubeba'' Lour". Journal of Functional Foods.
  12. (14 July 2016). "Antimicrobial Activity and Possible Mechanism of Action of Citral against ''Cronobacter sakazakii''". PLOS ONE.
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flavors perfume-ingredients monoterpenes conjugated-aldehydes
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