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A p p e a r a n c e
F r o m W i k i p e d i a , t h e f r e e e n c y c l o p e d i a
( R e d i r e c t e d f r o m N e r a l ( c i t r a l ) )
Citral[1]
Geranial
Neral
Names
IUPAC name
3,7-dimethylocta-2,6-dienal
Other names
citral
Identifiers
CAS Number
3D model (JSmol )
Interactive image
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.023.994
EC Number
IUPHAR/BPS
KEGG
PubChem CID
RTECS number
UNII
UN number
2810
CompTox Dashboard (EPA )
InChI=1S/C10H16O/c1-9(2 )5-4-6-10(3 )7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+ Y
Key: WTEVQBCEXWBHNA-JXMROGBWSA-N Y
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
Chemical formula
C 10 H 16 O
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)
Magnetic susceptibility (χ)
× 10 −6 cm 3
Hazards
GHS labelling
Pictograms
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
Flash point
91 °C (196 °F; 364 K )
Related compounds
Related alkenals
Methacrolein
trans -2-Methyl-2-butenal
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 geranial (trans -citral; α-citral[2] Z neral (cis -citral; β-citral[2] 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.[3]
Occurrence [ edit ]
Citral is present in the volatile oils of several plants, including lemon myrtle (90–98%), Litsea citrata Litsea cubeba lemongrass (65–85%), lemon tea-tree (70–80%), Ocimum gratissimum Lindera citriodora Calypranthes parriculata petitgrain (36%), lemon verbena (30–35%), lemon ironbark (26%), lemon balm (11%), lime (6–9%), lemon (2–5%), and orange .[4] [5] [6] [3] Backhousia citriodora Myrtaceae ), is considered superior.[7]
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.[7]
It also has pheromonal effects in acari and insects .[8] [9]
Citral is used in the synthesis of vitamin A , lycopene , ionone and methylionone , and to mask the smell of smoke.
The herb Cymbopogon citratus [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 pathogen Cronobacter sakazakii [12]
Medical exploration [ edit ]
In a report (1997), citral is mentioned as cytotoxic to P(388) mouse leukaemia cells.[10] antimicrobial qualities.[13]
Adverse effects [ edit ]
A number of studies have shown allergic reactions to Citral.[14] International Fragrance Association gives a no-observed-adverse-effect level of 1400 micrograms .[15] carcinogenic effect.[16]
See also [ edit ]
References [ edit ]
^ a b Zachariah, T. J.; Parthasarathy, V. A.; Chempakam, B. (2008). Chemistry of spices . Wallingford: CABI. p. 76. ISBN 9781845934057 OCLC 1120264204 .
^ Fenaroli, G.; Furia, T.E.; Bellanca, N. Handbook of Flavor Ingredients . ISBN 0-87819-532-7
^ Lawless, J. (2 November 1995). The Illustrated Encyclopedia of Essential Oils . Element. ISBN 1-85230-661-0
^ "The Aromatic Plant Project" . Archived from the original on 24 November 2019. Retrieved 1 June 2008 .
^ a b 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 .
^ 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
^ 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 .
^ a b 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 .
^ 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 doi :10.1016/j.jff.2015.09.034
^ 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 .
^ Onawunmi, Grace O. (September 1989). "Evaluation of the antimicrobial activity of citral". Letters in Applied Microbiology . 9 3 ): 105–108. doi :10.1111/j.1472-765X.1989.tb00301.x . S2CID 84751250 .
^ Hagvall, L.; Bruze, M.; Engfeldt, M.; Isaksson, M.; Lindberg, M.; Ryberg, K.; Stenberg, B.; Svedman, C.; Karlberg, A. T.; Bråred Christensson, J. (2020). "Contact allergy to citral and its constituents geranial and neral, coupled with reactions to the prehapten and prohapten geraniol". Contact Dermatitis . 82 1 ): 31–38. doi :10.1111/cod.13404 . PMID 31566752 .
^ "IRFA Standards, 47th Amendment: Citral" (PDF) . International Fragrance Association.
^ Andersen, Dorthe N.; Holmberg, Rikke D.; Larsen, Jette R.; Søborg, Inge; Cohr, Karl-Heinz (2006). Survey and health assessment of chemical substances in massage oils (PDF) . Survey of Chemical Substances in Consumer Products, No. 78. Danish Toxicology Centre.
External links [ edit ]
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Citral&oldid=1231589324 " C a t e g o r i e s : ● F l a v o r s ● P e r f u m e i n g r e d i e n t s ● M o n o t e r p e n e s ● C o n j u g a t e d a l d e h y d e s H i d d e n c a t e g o r i e s : ● U s e d m y d a t e s f r o m M a r c h 2 0 2 1 ● C h e m i c a l a r t i c l e s w i t h m u l t i p l e c o m p o u n d I D s ● M u l t i p l e c h e m i c a l s i n a n i n f o b o x t h a t n e e d i n d e x i n g ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● C h e m b o x h a v i n g G H S d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n i s d i f f e r e n t f r o m W i k i d a t a ● W e b a r c h i v e t e m p l a t e w a y b a c k l i n k s
● T h i s p a g e w a s l a s t e d i t e d o n 2 9 J u n e 2 0 2 4 , a t 0 3 : 5 4 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
