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Citral

From Wikipedia, the free encyclopedia

Not to be confused withGeraniol.
Citral[1]
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.023.994Edit this at Wikidata
EC Number
  • 226-394-6
KEGG
RTECS number
  • RG5075000
UNII
UN number2810
  • InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+ checkY
    Key: WTEVQBCEXWBHNA-JXMROGBWSA-N checkY
  • 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
  • O=CC=C(C)CCC=C(C)C
  • O=C/C=C(/CC/C=C(/C)C)C
Properties
C10H16O
Molar mass152.24 g/mol
AppearancePale yellow liquid
OdorLemon like
Density0.893 g/cm3
Boiling point229 °C (444 °F; 502 K)
Vapor pressure0.22 mmHg (20 °C)
−98.9×10−6 cm3/mol
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315,H317
P261,P264,P272,P280,P302+P352,P321,P332+P313,P333+P313,P362,P363,P501
NFPA 704 (fire diamond)
Flash point91 °C (196 °F; 364 K)
Related compounds
Related alkenals
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Citral is an acyclic monoterpene aldehyde. Being amonoterpene, it is made of twoisoprene units. Citral is a collective term which covers two geometric isomers that have their own separate names; theE-isomer is namedgeranial (trans-citral; α-citral[2]) or citral A. TheZ-isomer is namedneral (cis-citral; β-citral[2]) or citral B. Thesestereoisomers occur as a mixture, often not in equal proportions; e.g. in essential oil ofAustralian ginger, the neral to geranial ratio is 0.61.[3]

Natural Occurrence

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Citral is present in thevolatile oils of several plants:[4][5][6]

Further, in the lipid fraction (essential oil) of Australian ginger (51–71%)[3] Of the many sources of citral, the Australian myrtaceous tree, lemon myrtle,Backhousia citriodora F. Muell. (of the familyMyrtaceae), is considered superior.[7]

Uses

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

Citral is also precursor tolycopene,ionone andmethylionone.

Fragrances

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Citral has a strong lemon (citrus) scent and is used as anaroma 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.[7]

It also has pheromonal effects inacari andinsects.[8][9]

The herbCymbopogon citratus has shown promising insecticidal and antifungal activity against storage pests.[10]

Food additive

[edit]

Citral is commonly used as a food additive ingredient.[11]

It has been tested (2016) in vitro against the food-borne pathogenCronobacter sakazakii.[12]

See also

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References

[edit]
  1. ^Citral,The Merck Index, 12th Edition.
  2. ^abWaghulde, 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. ^abZachariah, 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 fromthe original on 24 November 2019. Retrieved1 June 2008.
  7. ^abSouthwell, 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 ofLitsea 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 againstCronobacter sakazakii".PLOS ONE.11 (7): e0159006.Bibcode:2016PLoSO..1159006S.doi:10.1371/journal.pone.0159006.PMC 4945043.PMID 27415761.

External links

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