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Citral

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(Redirected from Geranial)

Not to be confused with Geraniol.
Citral
Skeletal formula of geranial
Geranial
Ball-and-stick model of the geranial molecule
Skeletal formula of neral
Neral
Ball-and-stick model of the neral molecule
Names
IUPAC name 3,7-dimethylocta-2,6-dienal
Other names citral
geranialdehyde
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.023.994 Edit this at Wikidata
EC Number
  • 226-394-6
IUPHAR/BPS
KEGG
PubChem CID
RTECS number
  • RG5075000
UNII
UN number 2810
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+Key: WTEVQBCEXWBHNA-JXMROGBWSA-N
  • InChI=1/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+Key: WTEVQBCEXWBHNA-JXMROGBWBB
SMILES
  • O=CC=C(C)CCC=C(C)C
  • O=C/C=C(/CC/C=C(/C)C)C
Properties
Chemical formula C10H16O
Molar mass 152.24 g/mol
Appearance Pale yellow liquid
Odor Lemon like
Density 0.893 g/cm
Boiling point 229 °C (444 °F; 502 K)
Vapor pressure 0.22 mmHg (20 °C)
Magnetic susceptibility (χ) −98.9×10 cm/mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
Signal word Warning
Hazard statements H315, H317
Precautionary statements P261, P264, P272, P280, P302+P352, P321, P332+P313, P333+P313, P362, P363, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 0: Exposure under fire conditions would offer no hazard beyond that of ordinary combustible material. E.g. sodium chlorideFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
0 1 0
Flash point 91 °C (196 °F; 364 K)
Related compounds
Related alkenals
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

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.

Occurrence

Citral is present in the volatile 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. Further, in the lipid fraction (essential oil) of Australian ginger (51–71%) Of the many sources of citral, the Australian myrtaceous tree, lemon myrtle, Backhousia citriodora F. Muell. (of the 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.

See also

References

  1. Citral, The Merck Index, 12th Edition.
  2. ^ Waghulde, S.; Parmar, P.; Mule, J.; Pashte, D.; Patil, B.; Modhale, N.; Gorde, N.; Kharche, A.; Kale, M. (2020). "Lead Finding from Plant Cymbopogon Citratus with Immunomodulator Potentials through in Silico Methods". Chemistry Proceedings. 3 (1): 77. doi:10.3390/ecsoc-24-08302. ISSN 2673-4583.
  3. ^ Zachariah, T. J.; Parthasarathy, V. A.; Chempakam, B. (2008). Chemistry of spices. Wallingford: CABI. p. 76. ISBN 9781845934057. OCLC 1120264204.
  4. Fenaroli, G.; Furia, T.E.; Bellanca, N. Handbook of Flavor Ingredients. ISBN 0-87819-532-7.
  5. Lawless, J. (2 November 1995). The Illustrated Encyclopedia of Essential Oils. Element. ISBN 1-85230-661-0.
  6. "The Aromatic Plant Project". Archived from the original on 24 November 2019. Retrieved 1 June 2008.
  7. ^ Southwell, Ian (9 July 2021). "Backhousia citriodora F. Muell. (Lemon Myrtle), an Unrivalled Source of Citral". Foods. 10 (7): 1596. doi:10.3390/foods10071596. PMC 8305781. PMID 34359465.
  8. Kuwahara, Yasumasa; Suzuki, Hiroshi; Matsumoto, Katsuhiko; Wada, Yoshitake (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. 18 (1): 30–39. doi:10.1303/aez.18.30.
  9. Robacker, D.C.; Hendry, L.B. (1977). "Neral and geranial: components of the sex pheromone of the parasitic wasp, Itoplectis conquisitor". Journal of Chemical Ecology. 3 (5): 563–577. doi:10.1007/BF00989077. S2CID 11568355.
  10. Dubey, N. K.; Takeya, Koichi; Itokawa, Hideji (1997). "Citral: A cytotoxic principle isolated from the essential oil of Cymbopogon citratus against P388 leukaemia cells". Current Science. 73 (1): 22–24. JSTOR 24098141.
  11. Liao, Pei-Chun; Yang, Tsung-Shi; Chou, Ju-Ching; Chen, Jie; Lee, Shu-Ching; Kuo, Yueh-Hsiung; Ho, Chen-Lung; Chao, Louis Kuo-Ping (1 December 2015). "Anti-inflammatory activity of neral and geranial isolated from fruits of Litsea cubeba Lour". Journal of Functional Foods. 19: 248–258. doi:10.1016/j.jff.2015.09.034.
  12. Shi, Chao; Song, Kaikuo; Zhang, Xiaorong; Sun, Yi; Sui, Yue; Chen, Yifei; Jia, Zhenyu; Sun, Huihui; Sun, Zheng; Xia, Xiaodong (14 July 2016). "Antimicrobial Activity and Possible Mechanism of Action of Citral against Cronobacter sakazakii". PLOS ONE. 11 (7): e0159006. Bibcode:2016PLoSO..1159006S. doi:10.1371/journal.pone.0159006. PMC 4945043. PMID 27415761.

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