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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.

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]

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
^ Onawunmi, G.O. (1989). "Evaluation of the antimicrobial activity of citral". Lett. Appl. Microbial. 9 (3): 105–108. doi:10.1111/j.1472-765X.1989.tb00301.x.
^ Kuwahara, Y., Suzuki, H., Matsumoto, K. & Wada, Y. (1983). "Pheromone study on acarid mites. XI. Function of mite body as geometrical isomerization and reduction of citral (the alarm pheromone) Carpoglyphus lactis". Appl. Entomol. Zool. 18: 30–39.
^ Robacker, D.C.; Hendry, L.B. (1977). "Neral and geranial: components of the sex pheromone of the parasitic wasp, Itoplectis conquisitor". J. Chem. Ecol. 3 (5): 563–577. doi:10.1007/BF00989077.
^ Survey and health assessment of chemical substances in massage oils

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1. アレルギー性接触皮膚炎の一般的なアレルゲン common allergens in allergic contact dermatitis

English Journal

GC-MS evaluation of Cymbopogon citratus (DC) Stapf oil obtained using modified hydrodistillation and microwave extraction methods.

Ajayi EO1, Sadimenko AP1, Afolayan AJ2.
Food chemistry.Food Chem.2016 Oct 15;209:262-6. doi: 10.1016/j.foodchem.2016.04.071. Epub 2016 Apr 20.
Bioactive compounds of Cymbopogon citratus essential oil, using different media have been tentatively identified with the aid of gas chromatography-mass spectrometry (GC-MS). Hydrodistillation was complemented using weakly acidic and alkaline media for the oil extraction. Solvent-free microwave extr
PMID 27173561

Natural plant products inhibits growth and alters the swarming motility, biofilm formation, and expression of virulence genes in enteroaggregative and enterohemorrhagic Escherichia coli.

García-Heredia A1, García S1, Merino-Mascorro JÁ1, Feng P2, Heredia N3.
Food microbiology.Food Microbiol.2016 Oct;59:124-32. doi: 10.1016/j.fm.2016.06.001. Epub 2016 Jun 4.
The purpose of this study was to determine the effects of plant products on the growth, swarming motility, biofilm formation and virulence gene expression in enterohemorrhagic Escherichia coli O157:H7 and enteroaggregative E. coli strain 042 and a strain of O104:H4 serotype. Extracts of Lippia grav
PMID 27375253

Antimicrobial activity, cytotoxicity and chemical analysis of lemongrass essential oil (Cymbopogon flexuosus) and pure citral.

Adukwu EC1, Bowles M2, Edwards-Jones V3, Bone H2.
Applied microbiology and biotechnology.Appl Microbiol Biotechnol.2016 Aug 26. [Epub ahead of print]
The aim of this study was to determine the antimicrobial effects of lemongrass essential oil (C. flexuosus) and to determine cytotoxic effects of both test compounds on human dermal fibroblasts. Antimicrobial susceptibility screening was carried out using the disk diffusion method. Antimicrobial res
PMID 27562470

Japanese Journal

アロマキャンディのカンジダ発育阻止能とマウス口腔カンジダ症に対する防御効果

羽山和美,髙橋美貴,鈴木基文 [他],江澤邦夫,山﨑正利,松川泰治,來住明宣,佐藤喜哉,安部茂
Medical Mycology Journal 56(1), J23-J29, 2015
　<I>Candida albicans</I> の菌糸形発育を抑制することが知られているライチ由来ポリフェノールであるオリゴノール，カシア粉末，シトラール，カプリン酸などを含有するキャンディを作製し，口腔カンジダ症への適用の可能性を検討した．キャンディを水で溶解，希釈したものを <I>C. albicans</I> に添加し培養したところ，約 0. …
NAID 130005064304

Two types of alcohol dehydrogenase from Perilla can form citral and perillaldehyde.

Sato-Masumoto Naoko,Ito Michiho
Phytochemistry 104, 12-20, 2014-08
… In this study, two types of alcohol dehydrogenases, an aldo-keto reductase (AKR) and a geraniol dehydrogenase (GeDH), which are thought to participate in the biosynthesis of perilla essential oil components, such as citral and perillaldehyde, were isolated from three pure lines of perilla. … The overall reaction from geranyl diphosphate to citral was performed in vitro using geraniol synthase and GeDH to form a large proportion of citral and relatively little geraniol as reaction products. …
NAID 120005439534

カエル坐骨神経の複合活動電位に及ぼすアロマ精油成分の抑制作用

大坪瀬奈,藤田亜美,松下晋大,蒋昌宇,熊本栄一
PAIN RESEARCH 29(1), 17-30, 2014
… Citral, which activated TRPV1, TRPM8, TRPA1 and TRPV3 channels, attenuated CAP peak amplitudes with the IC50 value of 0.48 mM; … eugenol: 0.81 mM) ≧ aldehydes (citral and citronellal) ≧ esters (linaryl acetate) ＞ alcohols (linalool; …
NAID 130004839643

「シトラール」

Citral^[1]
	; Geranial
	; Neral
Names
	IUPAC name 3,7-dimethylocta-2,6-dienal
	Other names citral; geranialdehyde
Identifiers
CAS Number	5392-40-5
3D model (Jmol)	Interactive image; Interactive image
ChEBI	CHEBI:16980
ChEMBL	ChEMBL1080997
ChemSpider	553578
ECHA InfoCard	100.023.994
IUPHAR/BPS	6327
KEGG	C01499
PubChem	638011
RTECS number	RG5075000
UNII	T7EU0O9VPP
	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/cm3
Boiling point	229 °C (444 °F; 502 K)
Vapor pressure	0.22 mmHg (20 °C)
Magnetic susceptibility (χ)	-98.9·10−6 cm3/mol
Hazards
R-phrases	R36, R37, R38
NFPA 704	1 0 0
Flash point	91 °C (196 °F; 364 K)
Related compounds
Related alkenals	Citronellal; 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).
	verify (what is ?)
	Infobox references

　　[★]

英: citral
同: 3,7-ジメチル-2,6-オクタジエナール, 3,7-dimethyl-2,6-octadienal

[1] Citral, The Merck Index, 12th Edition.

[2] Fenaroli, G., Furia, T.E., Bellanca, N., Handbook of Flavor Ingredients, ISBN 0-87819-532-7

[3] Lawless, J., The Illustrated Encyclopedia of Essential Oils, ISBN 1-85230-661-0

[4] The Aromatic Plant Project

[5] Onawunmi, G.O. (1989). "Evaluation of the antimicrobial activity of citral". Lett. Appl. Microbial. 9 (3): 105–108. doi:10.1111/j.1472-765X.1989.tb00301.x.

[6] Kuwahara, Y., Suzuki, H., Matsumoto, K. & Wada, Y. (1983). "Pheromone study on acarid mites. XI. Function of mite body as geometrical isomerization and reduction of citral (the alarm pheromone) Carpoglyphus lactis". Appl. Entomol. Zool. 18: 30–39.

[7] Robacker, D.C.; Hendry, L.B. (1977). "Neral and geranial: components of the sex pheromone of the parasitic wasp, Itoplectis conquisitor". J. Chem. Ecol. 3 (5): 563–577. doi:10.1007/BF00989077.

[summary-8] Survey and health assessment of chemical substances in massage oils

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citral