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Chemical Compound Review

Rhodinal     3,7-dimethyloct-6-enal

Synonyms: Citronella, CITRONELLAL, Citronellel, D-Rhodinal, Rhodinal (VAN), ...
 
 
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Disease relevance of LS-2363

  • SBF analysis determined that cinnamon, cassia, and citronella oils differentially affected growth-normalized biofilm formation by Escherichia coli [1].
  • Detailed patch testing revealed contact allergic dermatitis to one of the twelve groups of ingredients which largely comprised citronella oil [2].
  • Recently our Centre handled five oil of citronella poisonings and their outcomes led us to review our management protocol which had been based on information from standard poisoning texts [3].
  • The management for ingestion of oil of citronella, an essential oil, has traditionally been rigorous, including dilution with milk or oil, and gastric lavage or emesis, taking care to prevent aspiration [3].
  • The source data used to determine the human toxicity of oil of citronella and the appropriate management of poisoning included a case report of a fatal ingestion of oil of citronella in a child [3].
 

High impact information on LS-2363

 

Biological context of LS-2363

  • (R)-(+)-citronellal and (S)-(-)-beta-citronellol inhibited P-gp with IC50 values of 167 microM and 504 microM, respectively [7].
  • Biotransformation of citronellal by Solanum aviculare suspension cultures: preparation of p-menthane-3,8-diols and determination of their absolute configurations [8].
  • This study was designed to evaluate the efficacy of a citronella bark collar and a new, scentless spray bark collar in a veterinary hospital or a similar kennel-type environment [9].
  • The stereogenic center at C-15 of 1 originated from that of the enantiomers of citronellal, and that at C-7 was generated by lipase-catalyzed asymmetric acetylation of (3RS,11R)- and (3RS,11S)-17-methyl-1-trimethylsilylpentacos-1-yn-3-ol (13) [10].
  • Cadmium at 200 mg kg-1 soil and above concentrations was fatal as growth was inhibited ultimately leading to death of Java citronella (Cymbopogon winterianus Jowitt.). The surviving plants at 50 and 100 mg kg-1 treatments also exhibited pronounced retardation of growth and biomass yield [11].
 

Anatomical context of LS-2363

 

Associations of LS-2363 with other chemical compounds

 

Gene context of LS-2363

 

Analytical, diagnostic and therapeutic context of LS-2363

  • Gas chromatography/olfactometry using Kabosu cold-pressed oil and its oxygenated fraction completed by a chiral analysis revealed that (R)-(+)-citronellal is a characteristic element of Kabosu peel oil odor [18].
  • The local lymph node assay was used to evaluate the dermal sensitization potential of basil, citronella, clove leaf, geranium, litsea cubeba, lemongrass, and palmarosa oils [19].
  • In a plastic container (4.5 by 9.5 cm) bioassay at 14 x 10(-3) microl/ml air, caraway seed, citronella java, lemon eucalyptus, pennyroyal, and peppermint oils gave > 90% mortality against adult T. urticae, whereas 82 and 81% mortality was observed with sage and spearmint oils, respectively [20].
  • In a laboratory study with female Aedes aegypti (L), fennel oil exhibited good repellency in a release-in-cage test and repellency in skin and patch tests of the oil was comparable with those of citronella and geranium oils [21].
  • In accord with this, skin tests with the mixture yielded positive results in nearly all cases of hypersensitivity to citronella or cassia oil and in these cases only [22].

References

  1. Colorimetric method for identifying plant essential oil components that affect biofilm formation and structure. Niu, C., Gilbert, E.S. Appl. Environ. Microbiol. (2004) [Pubmed]
  2. Contact dermatitis from an ostomy deodorant. Davies, M.G., Hodgson, G.A., Evans, E. Contact Derm. (1978) [Pubmed]
  3. Management of oil of citronella poisoning. Temple, W.A., Smith, N.A., Beasley, M. J. Toxicol. Clin. Toxicol. (1991) [Pubmed]
  4. Identification of specific ligands for orphan olfactory receptors. G protein-dependent agonism and antagonism of odorants. Shirokova, E., Schmiedeberg, K., Bedner, P., Niessen, H., Willecke, K., Raguse, J.D., Meyerhof, W., Krautwurst, D. J. Biol. Chem. (2005) [Pubmed]
  5. Domino-cyclisation and hydrogenation of citronellal to menthol over bifunctional Ni/Zr-Beta and Zr-beta/Ni-MCM-41 catalysts. Nie, Y., Chuah, G.K., Jaenicke, S. Chem. Commun. (Camb.) (2006) [Pubmed]
  6. Effects of citronellal, a monoterpenoid in Zanthoxyli Fructus, on the intestinal absorption of digoxin in vitro and in vivo. Yoshida, N., Takagi, A., Kitazawa, H., Kawakami, J., Adachi, I. Journal of pharmaceutical sciences. (2006) [Pubmed]
  7. Inhibition of P-glycoprotein-mediated transport by extracts of and monoterpenoids contained in Zanthoxyli fructus. Yoshida, N., Takagi, A., Kitazawa, H., Kawakami, J., Adachi, I. Toxicol. Appl. Pharmacol. (2005) [Pubmed]
  8. Biotransformation of citronellal by Solanum aviculare suspension cultures: preparation of p-menthane-3,8-diols and determination of their absolute configurations. Vanek, T., Novotný, M., Podlipná, R., Saman, D., Valterová, I. J. Nat. Prod. (2003) [Pubmed]
  9. Effectiveness and comparison of citronella and scentless spray bark collars for the control of barking in a veterinary hospital setting. Moffat, K.S., Landsberg, G.M., Beaudet, R. Journal of the American Animal Hospital Association. (2003) [Pubmed]
  10. Synthesis of the four stereoisomers of 7-acetoxy-15-methylnonacosane, a component of the female sex pheromone of the screwworm fly, Cochliomyia hominivorax. Mori, K., Ohtaki, T., Ohrui, H., Berkebile, D.R., Carlson, D.A. Biosci. Biotechnol. Biochem. (2004) [Pubmed]
  11. Response of Java citronella (Cymbopogon winterianus Jowitt) to toxic heavy metal cadmium. Boruah, H.P., Handique, A.K., Borah, G.C. Indian J. Exp. Biol. (2000) [Pubmed]
  12. Effects of azadirachtin on Ctenocephalides felis in the dog and the cat. Guerrini, V.H., Kriticos, C.M. Vet. Parasitol. (1998) [Pubmed]
  13. Inhibition of P-glycoprotein-mediated transport by terpenoids contained in herbal medicines and natural products. Yoshida, N., Koizumi, M., Adachi, I., Kawakami, J. Food Chem. Toxicol. (2006) [Pubmed]
  14. Comparative repellency of commercial formulations of deet, permethrin and citronellal against the mosquito Aedes aegypti, using a collagen membrane technique compared with human arm tests. Cockcroft, A., Cosgrove, J.B., Wood, R.J. Med. Vet. Entomol. (1998) [Pubmed]
  15. Repelling properties of some plant materials on the tick Ixodes ricinus L. Thorsell, W., Mikiver, A., Tunón, H. Phytomedicine (2006) [Pubmed]
  16. Effect of urine-derived compounds on cAMP accumulation in mouse vomeronasal cells. Zhou, A., Moss, R.L. Neuroreport (1997) [Pubmed]
  17. Real-time monitoring of particles, PAH, and CO in an occupied townhouse. Wallace, L. Applied occupational and environmental hygiene. (2000) [Pubmed]
  18. Characteristic odor components of Citrus sphaerocarpa Tanaka (Kabosu) cold-pressed peel oil. Minh Tu, N.T., Onishi, Y., Choi, H.S., Kondo, Y., Bassore, S.M., Ukeda, H., Sawamura, M. J. Agric. Food Chem. (2002) [Pubmed]
  19. Investigation of the dermal sensitization potential of various essential oils in the local lymph node assay. Lalko, J., Api, A.M. Food Chem. Toxicol. (2006) [Pubmed]
  20. Toxicity of plant essential oils to Tetranychus urticae (Acari: Tetranychidae) and Phytoseiulus persimilis (Acari: Phytoseiidae). Choi, W.I., Lee, S.G., Park, H.M., Ahn, Y.J. J. Econ. Entomol. (2004) [Pubmed]
  21. Repellency of aerosol and cream products containing fennel oil to mosquitoes under laboratory and field conditions. Kim, S.I., Chang, K.S., Yang, Y.C., Kim, B.S., Ahn, Y.J. Pest Manag. Sci. (2004) [Pubmed]
  22. The value of a mixture of cassia and citronella oils for detection of hypersensitivity of essential oils. Rudzki, E., Grzywa, Z. Dermatosen in Beruf und Umwelt. Occupation and environment. (1985) [Pubmed]
 
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