Citral, mixture of cis and trans - CAS 5392-40-5
Catalog number: 5392-40-5
Category: Intermediates
Molecular Formula:
Molecular Weight:
A clear yellow colored liquid with a lemon-like odor. Less dense than water and insoluble in water. Toxic by ingestion. Used to make other chemicals.
(2E)-3,7-Dimethyl-2,6-octadienal; 2,6-Octadienal, 3,7-dimethyl-; 2,6-Octadienal,3,7-dimethyl-; 3,7-Dimethyl-1,2,6-octadienal; 3,7-Dimethyll-2,6-octadienal; 3,7-dimethyl-octa-2,6-dienal; 6-Octadienal,3,7-dimethyl-2; cis,trans-Citral
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Citral, mixture of cis and trans 95% (500ml)
1.Essential oil of Lippia alba and its main constituent citral block the excitability of rat sciatic nerves.
Sousa DG1, Sousa SD1, Silva RE1, Silva-Alves KS2, Ferreira-da-Silva FW2, Kerntopf MR3, Menezes IR3, Leal-Cardoso JH2, Barbosa R1. Braz J Med Biol Res. 2015 Aug;48(8):697-702. doi: 10.1590/1414-431X20154710. Epub 2015 Jun 30.
Lippia alba is empirically used for infusions, teas, macerates, and hydroalcoholic extracts because of its antispasmodic, analgesic, sedative, and anxiolytic effects. Citral is a mixture of trans-geranial and cis-neral and is the main constituent of L. alba essential oil and possesses analgesic, anxiolytic, anticonvulsant, and sedative effects. The present study evaluated the effects of the essential oil of L. alba (EOLa) and citral on compound action potentials (CAPs) in Wistar rat sciatic nerves. Both drugs inhibited CAP in a concentration-dependent manner. The calculated half-maximal inhibitory concentrations (IC50) of peak-to-peak amplitude were 53.2 µg/mL and 35.00 µg/mL (or 230 µM) for EOLa and citral, respectively. Peak-to-peak amplitude of the CAP was significantly reduced by 30 µg/mL EOLa and 10 µg/mL citral. EOLa and citral (at 60 and 30 µg/mL, values close to their respective IC50 for CAP blockade) significantly increased chronaxy and rheobase.
2.Formulation, Characterization, and Antitumor Properties of Trans- and Cis-Citral in
Zeng S1, Kapur A, Patankar MS, Xiong MP. Pharm Res. 2015 Aug;32(8):2548-58. doi: 10.1007/s11095-015-1643-0. Epub 2015 Feb 12.
PURPOSE: Citral is composed of a random mixture of two geometric stereoisomers geranial (trans-citral) and neral (cis-citral) yet few studies have directly compared their in vivo antitumor properties. A micelle formulation was therefore developed.
3.Effect of 2-Propanol on the Transfer Hydrogenation of Aldehydes by Aqueous Sodium Formate using a Rhodium(I)-sulfonated Triphenylphosphine Catalyst.
Kathó Á1, Szatmári I2, Papp G3, Joó F4. Chimia (Aarau). 2015;69(6):339-44. doi: 10.2533/chimia.2015.339.
In water/2-propanol mixtures [RhCl(mtppms)(3)] (mtppms = monosulfonated triphenylphosphine) was an efficient catalyst for the selective C=C reduction of trans-3-phenyl-2-propenal (trans-cinnamaldehyde) by hydrogen transfer from formate at temperatures as low as 30 °C. An outstandingly high catalyst turnover frequency of 1214 h(-1) was determined at 70 °C. A possible mechanism of the reaction is suggested on the basis of kinetic studies and (1)H- and (31)P-NMR spectroscopic identification of the major Rh(I) species in the reaction mixtures as cis-mer-[H(2)RhX(mtppms)(3)] (X = HCOO(-) or H(2)O). It was established that a large part but not all of the rate increase observed in water/2-propanol mixtures in comparison with systems with neat water as solvent was the consequence of complete dissolution of trans-cinnamaldehyde on the effect of the co-solvent. Nevertheless, the rate showed a significant further increase with increasing 2-propanol concentration even in homogeneous solution and this was ascribed to changes in the solvent structure.
4.Mechanism of inhibition of aldehyde dehydrogenase by citral, a retinoid antagonist.
Kikonyogo A1, Abriola DP, Dryjanski M, Pietruszko R. Eur J Biochem. 1999 Jun;262(3):704-12.
Low concentrations of citral (3,7-dimethyl-2,6-octadienal), an inhibitor of retinoic acid biosynthesis, inhibited E1, E2 and E3 isozymes of human aldehyde dehydrogenase (EC1.2.1.3). The inhibition was reversible on dilution and upon long incubation in the presence of NAD+; it occurred with simultaneous formation of NADH and of geranic acid. Thus, citral is an inhibitor and also a substrate. Km values for citral were 4 microM for E1, 1 microM for E2 and 0.1 microM for E3; Vmax values were highest for E1 (73 nmol x min-1 x mg-1), intermediate for E2 (17 nmol x min-1 x mg-1) and lowest (0.07 nmol x min-1 x mg-1) for the E3 isozyme. Citral is a 1 : 2 mixture of isomers: cis isomer neral and trans isomer, geranial; the latter structurally resembles physiologically important retinoids. Both were utilized by all three isozymes; a preference for the trans isomer, geranial, was observed by HPLC and by enzyme kinetics. With the E1 isozyme, both geranial and neral, and with the E2 isozyme, only neral obeyed Michaelis-Menten kinetics.
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