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Chemical Compound Review

GERANIAL     (2E)-3,7-dimethylocta-2,6- dienal

Synonyms: Genanial, geranal, Citral, Geranaldehyde, geranialdehyde, ...
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Disease relevance of Citral

  • The results presented confirm the previous suggestion that a free radical-peroxide mechanism is involved in citral induced hemolysis [1].
  • Early stages of the pathogenesis of rat ventral prostate hyperplasia induced by citral [2].
  • When tested against Fusarium oxysporum and F. solani, fungal root pathogens of Citrus, enhanced toxicity by citral in the presence of UV-A was demonstrated, while dark toxicity was negligible [3].
  • Typical lesions of benign prostatic hyperplasia (BPH) were induced experimentally in the ventral prostate of adolescent (6 week old) male rats by citral, a nonsteroidal compound [2].
  • Those E. coli strains carrying a gene leading to catalase deficiency (katF) are particularly sensitized to inactivation by citral and UV-A treatment when compared to catalase proficient strains (katF+) [3].

Psychiatry related information on Citral

  • On postnatal day 11, oligodeoxynucleotides were infused directly into the bilateral olfactory bulbs through cannulae implanted prior to training in a classical conditioning paradigm with citral odor and foot shock [4].

High impact information on Citral

  • The formation of these spinules during light adaptation is impaired in the presence of citral, a competitive inhibitor of the dehydrogenase responsible for the generation of retinoic acid in vivo [5].
  • The feasibility of this approach was demonstrated by the ability of citral treatment and v-erbA mRNA injection to reduce the teratogenic effects of exogenous retinol and retinoic acid, respectively, in early Xenopus development [6].
  • Interestingly, v-erbA mRNA injection and citral treatment of gastrula stage embryos resulted in tadpoles with a similar set of developmental defects [6].
  • Although citral had little effect on epidermal ornithine decarboxylase activity when applied alone, it potentiated the induction of ornithine decarboxylase activity by 12-O-tetradecanoylphorbol-13-acetate [7].
  • Consistent with this idea, exogenous FGF8 was able to prevent cell death, rescue most of the morphological defects and was able to prevent a decrease in retinoic acid receptorbeta (Rarbeta) expression caused by Citral [8].

Chemical compound and disease context of Citral


Biological context of Citral

  • The mechanism of Citral effects was a specific increase in programmed cell death on the lateral (lateral nasal prominence) but not the medial side (frontonasal mass) of the nasal pit [8].
  • Citral prevented upregulation of Fgf8 along the lateral edge and this may have contributed to the specific increase in programmed cell death in the lateral nasal prominence [8].
  • MgCo6Ge6 possesses a remarkable activity and selectivity for the hydrogenation of cis/trans-citral to geraniol and nerol [13].
  • Compared to ROH alone, ROH plus citral treatment resulted in three-fold less tRA synthesis and a > 65% attentuation of RA-responsive reporter gene activity which persisted through 72 h [14].
  • This hypothetical cascade of RA signaling was supported by our findings that inhibition of the ROL-->RA converting enzyme system by citral abolished the Ca2+-mediated transactivation of the CAT gene in a nontoxic manner [15].

Anatomical context of Citral

  • These citral-treated limb buds frequently formed truncated cartilage elements and the defects were rescued by simultaneous treatment with an appropriate concentration of RA [16].
  • Thus, citral is not suitable for use in attempts to distinguish between retinoid conversions catalyzed by dehydrogenases in the cytoplasm and by P450 cytochromes in the endoplasmic reticulum [17].
  • CFA itself, however, had a proliferative action on the prostatic epithelium, and it augmented the hyperplastic changes induced by citral and even induced atypical transformations of the acinar epithelium [18].
  • The concentration of intracellular glutathione diminished in citral treated erythrocytes [1].
  • RESULTS: CsA did not induce hyperplastic changes or abolish the ability of citral to promote hyperplastic changes or to affect the extent of the lymphocytic exudate in the stroma [18].

Associations of Citral with other chemical compounds


Gene context of Citral

  • The MEK inhibitor PD98059 was continuously infused into the OB of postnatal day 11 rat pups during a 30-min training session regarding the pairing of citral odor and foot shock [24].
  • The Vmax for citral with the E1 isozyme was higher than those of the E2 and E3 isozymes which explains its fast recovery following inhibition by citral and suggests that E1 may be the enzyme involved in vivo citral metabolism [25].
  • We have carried out experiments that have used Citral, a RALDH antagonist, to address the function of retinoid signaling from the nasal pit in a whole embryo model [8].
  • In the first experiment, postnatal day 11 rat pups were trained in an olfactory associative learning task with citral odor and foot shock as the conditioned and unconditioned stimuli, respectively [26].
  • Evidence of ALDH-mediated citral oxidation was not seen in either subcellular fraction [27].

Analytical, diagnostic and therapeutic context of Citral

  • Castration prior to citral administration prevented such BPH changes; however, citral did not prevent the involutive lesions of castration [2].
  • A study of the potential effects of microencapsulation on the toxicity of citral was conducted in 14-day continuous feeding studies with both sexes of F344 rats and B6C3F1 mice [28].
  • The HPLC method developed in this study showed an excellent performance (linearity, precision, accuracy and specificity) and can be applied to assay citral in volatile oil [29].
  • The reference method for both types of oil was the BP monograph titration assay for the citral content of lemon oil and calibrations were constructed using these reference data [30].
  • Low doses of citral and geraniol (threshold ca. 10(-4) M) reversibly increased the frequency of spontaneous foregut contractions and abolished them at 2 x 10(-3) M (together with response to electrical stimulation) [31].


  1. The hemolytic activity of citral--II. Glutathione depletion in citral treated erythrocytes. Segal, R., Milo-Goldzweig, I. Biochem. Pharmacol. (1985) [Pubmed]
  2. Early stages of the pathogenesis of rat ventral prostate hyperplasia induced by citral. Servadio, C., Abramovici, A., Sandbank, U., Savion, M., Rosen, M. Eur. Urol. (1986) [Pubmed]
  3. Mechanisms of citral phototoxicity. Asthana, A., Larson, R.A., Marley, K.A., Tuveson, R.W. Photochem. Photobiol. (1992) [Pubmed]
  4. Activation of the cyclic AMP response element-binding protein signaling pathway in the olfactory bulb is required for the acquisition of olfactory aversive learning in young rats. Zhang, J.J., Okutani, F., Inoue, S., Kaba, H. Neuroscience (2003) [Pubmed]
  5. Retinoic acid has light-adaptive effects on horizontal cells in the retina. Weiler, R., Schultz, K., Pottek, M., Tieding, S., Janssen-Bienhold, U. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  6. v-erbA and citral reduce the teratogenic effects of all-trans retinoic acid and retinol, respectively, in Xenopus embryogenesis. Schuh, T.J., Hall, B.L., Kraft, J.C., Privalsky, M.L., Kimelman, D. Development (1993) [Pubmed]
  7. Oxidation of retinol to retinoic acid as a requirement for biological activity in mouse epidermis. Connor, M.J. Cancer Res. (1988) [Pubmed]
  8. Control of retinoic acid synthesis and FGF expression in the nasal pit is required to pattern the craniofacial skeleton. Song, Y., Hui, J.N., Fu, K.K., Richman, J.M. Dev. Biol. (2004) [Pubmed]
  9. The hemolytic activity of citral: evidence for free radical participation. Tamir, I., Abramovici, A., Milo-Goldzweig, I., Segal, R. Biochem. Pharmacol. (1984) [Pubmed]
  10. Toxicity of terpenes to spores and mycelium of Penicillium digitatum. Wolken, W.A., Tramper, J., van der Werf, M.J. Biotechnol. Bioeng. (2002) [Pubmed]
  11. Retinoic acid reverses ethanol-induced cardiovascular abnormalities in quail embryos. Twal, W.O., Zile, M.H. Alcohol. Clin. Exp. Res. (1997) [Pubmed]
  12. Toxic effects of lemon peel constituents on Ceratitis capitata. Salvatore, A., Borkosky, S., Willink, E., Bardón, A. J. Chem. Ecol. (2004) [Pubmed]
  13. Synthesis, crystal structure, and catalytic properties of MgCo6Ge6. Gieck, C., Schreyer, M., Fässler, T.F., Cavet, S., Claus, P. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  14. Metabolic conversion of retinol to retinoic acid mediates the biological responsiveness of human mammary epithelial cells to retinol. Hayden, L.J., Hawk, S.N., Sih, T.R., Satre, M.A. J. Cell. Physiol. (2001) [Pubmed]
  15. Retinoic acid signaling cascade in differentiating murine epidermal keratinocytes: alterations in papilloma- and carcinoma-derived cell lines. Vettermann, O., Siegenthaler, G., Winter, H., Schweizer, J. Mol. Carcinog. (1997) [Pubmed]
  16. Citral, an inhibitor of retinoic acid synthesis, modifies chick limb development. Tanaka, M., Tamura, K., Ide, H. Dev. Biol. (1996) [Pubmed]
  17. Metabolism of all-trans, 9-cis, and 13-cis isomers of retinal by purified isozymes of microsomal cytochrome P450 and mechanism-based inhibition of retinoid oxidation by citral. Raner, G.M., Vaz, A.D., Coon, M.J. Mol. Pharmacol. (1996) [Pubmed]
  18. Role of chronic inflammation in the promotion of prostatic hyperplasia in rats. Kessler, O.J., Keisari, Y., Servadio, C., Abramovici, A. J. Urol. (1998) [Pubmed]
  19. Terminal-group oxidation of retinol by mouse epidermis. Inhibition in vitro and in vivo. Connor, M.J., Smit, M.H. Biochem. J. (1987) [Pubmed]
  20. A phase II detoxification enzyme inducer from lemongrass: identification of citral and involvement of electrophilic reaction in the enzyme induction. Nakamura, Y., Miyamoto, M., Murakami, A., Ohigashi, H., Osawa, T., Uchida, K. Biochem. Biophys. Res. Commun. (2003) [Pubmed]
  21. Retinoids during the in vitro transition from bovine morula to blastocyst. Rodríguez, A., Diez, C., Ikeda, S., Royo, L.J., Caamaño, J.N., Alonso-Montes, C., Goyache, F., Alvarez, I., Facal, N., Gomez, E. Hum. Reprod. (2006) [Pubmed]
  22. Allergic contact dermatitis resulting from sensitivity to citrus peel, geraniol, and citral. Cardullo, A.C., Ruszkowski, A.M., DeLeo, V.A. J. Am. Acad. Dermatol. (1989) [Pubmed]
  23. Early changes in murine epidermal cell phenotype by contact sensitizers. Coutant, K.D., Ulrich, P., Thomas, H., Cordier, A., Brugerolle de Fraissinette, A. Toxicol. Sci. (1999) [Pubmed]
  24. Activation of the mitogen-activated protein kinase/extracellular signal-regulated kinase signaling pathway leading to cyclic AMP response element-binding protein phosphorylation is required for the long-term facilitation process of aversive olfactory learning in young rats. Zhang, J.J., Okutani, F., Inoue, S., Kaba, H. Neuroscience (2003) [Pubmed]
  25. Mechanism of inhibition of aldehyde dehydrogenase by citral, a retinoid antagonist. Kikonyogo, A., Abriola, D.P., Dryjanski, M., Pietruszko, R. Eur. J. Biochem. (1999) [Pubmed]
  26. Gabaergic control of olfactory learning in young rats. Okutani, F., Yagi, F., Kaba, H. Neuroscience (1999) [Pubmed]
  27. The metabolism of 3,7-dimethyl-2,6-octadienal (citral) in rat hepatic mitochondrial and cytosolic fractions. Interactions with aldehyde and alcohol dehydrogenases. Boyer, C.S., Petersen, D.R. Drug Metab. Dispos. (1991) [Pubmed]
  28. Comparison of the toxicity of citral in F344 rats and B6C3F1 mice when administrated by microencapsulation in feed or by corn-oil gavage. Dieter, M.P., Goehl, T.J., Jameson, C.W., Elwell, M.R., Hildebrandt, P.K., Yuan, J.H. Food Chem. Toxicol. (1993) [Pubmed]
  29. LC determination of citral in Cymbopogon citratus volatile oil. Rauber, C.d.a. .S., Guterres, S.S., Schapoval, E.E. Journal of pharmaceutical and biomedical analysis. (2005) [Pubmed]
  30. The quantification of citral in lemongrass and lemon oils by near-infrared spectroscopy. Wilson, N.D., Ivanova, M.S., Watt, R.A., Moffat, A.C. J. Pharm. Pharmacol. (2002) [Pubmed]
  31. Comparison of effects of octopamine and insecticidal essential oils on activity in the nerve cord, foregut, and dorsal unpaired median neurons of cockroaches. Price, D.N., Berry, M.S. J. Insect Physiol. (2006) [Pubmed]
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