2D Structure
3D Structure
| Properties | |
|---|---|
| PID | PID00057 |
| Mol. Weight | 152.237 g/mol |
| LogP | 2.66 |
| Water solubility | 0.00263 mol/L at 20 °C |
| Hydrogen Bond Donor | 0 |
| Hydrogen Bond Acceptor | 1 |
| Rotatable Bonds | 4 |
| XLogP3 | 3.0 |
| Identifiers | |
|---|---|
| Formula | C10H16O |
| PubChem CID | 638011 |
| FEMA | 2303 |
| Flavor Profile | Strong Lemon Odor, Characteristic Bittersweet; Lemon |
| Smiles | CC(C)=CCC/C(C)=C/C=O |
| InChl Key | WTEVQBCEXWBHNA-JXMROGBWSA-N |
| InChl | InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+ |
| CAS Registry Number | 5392-40-5, 141-27-5, 147060-73-9 |
| IUPAC Systematic Name | (2E)-3,7-dimethylocta-2,6-dienal |
Organ Location Map/System Distribution of Pungent Flavor Compounds’ Targets
Note: Known Targets (Gene) from 6952 literatures, DrugBank (http://www.drugbank.ca/), STITCH (http://stitch.embl.de/), ChEMBL (https://www.ebi.ac.uk/chembl/), Therapeutic Target Database (http://bidd.nus.edu.sg/group/ttd/), and Comparative Toxicogenomics Database (CTD, http://ctdbase.org/)
| English Name | Pinyin Name (Chinese Name) | Latin Name | Properties in TCM | merdians | View Graph |
|---|---|---|---|---|---|
| Tsaoko | Cao Guo (草果) | Tsaoko Fructus | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Allium fistulosum | Cong Bai(葱白) | Fistular Onion | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
| Common Ginger Dried Rhizome | Gan Jiang (干姜) | Zingiberis Rhizoma | Hot, Pungent | Lung, Spleen, Stomach, Heart, Kidney | View Graph |
| Forsythia suspensa | Lian Qiao(连翘) | Weeping Forsythia | Minor cold,Bitter | Lung,Stomach | View Graph |
| Ganoderma lucidum | Ling Zhi(灵芝) | Lucid Ganoderma Equivalent plant: Ganoderma japoni | Mild,Sweet | Lung,Spleen | View Graph |
| Flos Campsis | Ling Xiao Hua(凌霄花) | flower of Common Trumpetcreeper | Minor cold,Pungent | Liver,Cardiovascular | View Graph |
| rhizome of Obscured Homalomena | Qian Nian Jian(千年健) | Homalomenae Rhizoma | Warm, Bitter, Pungent | Spleen, Large Intestine, Stomach, Gallbladder, Three End | View Graph |
| Bugbane Equivalent plant: Cimicifuga dahurica, Ci | Sheng Ma(升麻) | Cimicifugae Rhizoma | Cold, Sweet, Pungent | Lung, Spleen, Large Intestine, Stomach | View Graph |
| Fresh Common Ginger | Sheng Jiang (生姜) | Zingiber Rhizoma Recens | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Wilson Citron | Xiang Yuan(香橼) | Citri Fructus | Warm, Pungent, Sour, Slightly Bitter | Lung, Spleen, Liver | View Graph |
| Lily Magnolia Buds Equivalent plant: Magnolia lili | Xin Yi (辛夷) | Magnoliae Flos | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Coriandrum sativum L | Yan Sui(芫荽) | Cilantro | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Perilla frutescens var. arguta | Zi Su(紫苏) | Common Perilla Equivalent plant: Perilla frutescen | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Prepared Ginger | Pao Jiang(炮姜) | Rhizoma Zingiberis Praeparata | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
| Allium sativum | Da Suan(大蒜) | Garlic | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
| Bunge Pricklyash Equivalent plant: Zanthoxylum sch | Hua Jiao (花椒) | Zanthoxyli Pericarpium | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
| Fortune Eupatorium Equivalent plant: Eupatorium f | Pei Lan(佩兰) | Eupatorii Herba | Neural, Pungent | Lung,Spleen,Stomach | View Graph |
| Apple Mint | Yu Xian Cao(鱼腥草) | Houttuyniae Herba | Cold, Pungent | Lung | View Graph |
| Piper cubeba | Bi Cheng Qie(荜澄茄) | Cubeba Pepper | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Tsaoko | Cao Guo (草果) | Tsaoko Fructus | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Ternate Pinellia | Ban Xia(半夏) | Pinellia ternata | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
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. Citral is a major active component of citrus oils, which are already commonly used in foods and beverages (e.g., sof drinks and deserts). Citral, a bioactive component of lemongrass, is commonly used as a taste enhancer, as an odorant in perfumes, and as an insect repellent.
Citral, a naturally occurring isoprenoid with two isomers (geranial and neral), reportedly exerts strong anti-fungal activity against P. digitatum. Citral, a pure mixture of the two monoterpenoid isomers, neral and geranial, is a widely used food additive approved by the US Food and Drug Administration as generally safe for human and animal consumption.
Citral could also induce a decrease in the TCA-related enzyme activities of A. flavus. Citral is a major compound of lemongrass (Cymbopogon citratus L.) that has many pharmacological activities such as anti-fungal and anti-bacterial effects.
Citral is a major active component of citrus oils, which are already commonly used in foods and beverages (e.g., sof drinks and deserts). Citral is approved for
use in foods by the Food and Drug Administration (FDA, GRAS, 21 CFR 18260). In addition, citral has been proven to exhibit antibacterial activity on Escherichia
coli, Salmonella and Listeria monocytogenes.
Note: Click anywhere in the blank, you can drag the whole dynamic diagram. Click on a node, you can drag his location to see it more clearly. The blue circle represents pharmacology, toxicology, or daily use. Orange hexagon represents the pungent compounds.
1. https://en.wikipedia.org/wiki/Citral
2. Saha D, Leong K, Li C, et al. A spatiotemporal coding mechanism for background-invariant odor recognition[J]. Nature neuroscience, 2013, 16(12): 1830.
3. Zhou H, Tao N, Jia L. Antifungal activity of citral, octanal and -terpineol against Geotrichum citri-aurantii[J]. Food Control, 2014, 37: 277-283.
4. Blum M S, Kerr W E, Fales H M. The chemical basis of insect sociality[J]. Chemicals controlling insect behavior, 1970: 61-94.
5. Zheng, S., Jing, G., Wang, X., Ouyang, Q., Jia, L., Tao, N. Citral exerts its antifungal activity against Penicillium digitatum by affecting the mitochondrial morphology and function[J]. Food chemistry, 2015, 178: 76-81.
6. Wuryatmo E, Klieber A, Scott E S. Inhibition of citrus postharvest pathogens by vapor of citral and related compounds in culture[J]. Journal of agricultural and food chemistry, 2003, 51(9): 2637-2640.
7. Nogueira, J. H., Gon?alez, E., Galleti, S. R., Facanali, R., Marques, M. O., Felcio, J. D. Ageratum conyzoides essential oil as aflatoxin suppressor of Aspergillus flavus[J]. International Journal of Food Microbiology, 2010, 137(1): 55-60.
8. Park, M. J., Gwak, K. S., Yang, I., Kim, K. W., Jeung, E. B., Chang, J. W., & Choi, I. G. Effect of citral, eugenol, nerolidol and -terpineol on the ultrastructural changes of Trichophyton mentagrophytes[J]. Fitoterapia, 2009, 80(5): 290-296.
9. Romagnoli, C., Bruni, R., Andreotti, E., Rai, M. K., Vicentini, C. B., Mares, D. Chemical characterization and antifungal activity of essential oil of capitula from wild Indian Tagetes patula L[J]. Protoplasma, 2005, 225(1-2): 57-65.
10. Bakkali, F., Averbeck, S., Averbeck, D., Idaomar, M. Biological effects of essential oilsCa review[J]. Food and chemical toxicology, 2008, 46(2): 446-475.
11. Zheng, S., Jing, G., Wang, X., Ouyang, Q., Jia, L., Tao, N. Citral exerts its antifungal activity against Penicillium digitatum by affecting the mitochondrial morphology and function[J]. Food chemistry, 2015, 178: 76-81.
12. Siroli, L., Patrignani, F., Gardini, F., Lanciotti, R. Effects of sub-lethal concentrations of thyme and oregano essential oils, carvacrol, thymol, citral and trans-2-hexenal on membrane fatty acid composition and volatile molecule profile of Listeria monocytogenes, Escherichia coli and Salmonella enteritidis[J]. Food chemistry, 2015, 182: 185-192.
13. De Souza, F. M. S., Busquet, N., Blatner, M., Maclean, K. N., Restrepo, D. Galantamine improves olfactory learning in the Ts65Dn mouse model of Down syndrome[J]. Scientific reports, 2011, 1: 137.
14. Mombaerts P. Genes and ligands for odorant, vomeronasal and taste receptors[J]. Nature Reviews Neuroscience, 2004, 5(4): 263.
15. Knaapila, A., Keskitalo, K., Kallela, M., Wessman, M., Sammalisto, S., Hiekkalinna, T., Perola, M. Genetic component of identification, intensity and pleasantness of odours: a Finnish family study[J]. European Journal of Human Genetics, 2007, 15(5): 596.
16. Steinkellner, G., Gruber, C. C., Pavkov-Keller, T., Binter, A., Steiner, K., Winkler, C., Faber, K. Identification of promiscuous ene-reductase activity by mining structural databases using active site constellations[J]. Nature communications, 2014, 5: 4150.
17. Shi, C., Sun, Y., Liu, Z., Guo, D., Sun, H., Sun, Z., Xia, X. Inhibition of Cronobacter sakazakii virulence factors by citral[J]. Scientific reports, 2017, 7: 43243.
18. Friedman, M., Henika, P. R., Levin, C. E., & Mandrell, R. E. Antibacterial activities of plant essential oils and their components against Escherichia coli O157: H7 and Salmonella enterica in apple juice[J]. Journal of agricultural and food chemistry, 2004, 52(19): 6042-6048.
19. Silva-Angulo, A. B., Zanini, S. F., Rosenthal, A., Rodrigo, D., Klein, G., Martnez, A. Combined effect of carvacrol and citral on the growth of Listeria monocytogenes and Listeria innocua and on the occurrence of damaged cells[J]. Food Control, 2015, 53: 156-162.
20. Somolinos, M., Garca, D., Condn, S., Mackey, B., & Pagn, R. Inactivation of Escherichia coli by citral[J]. Journal of applied microbiology, 2010, 108(6): 1928-1939.
21. Lee, H. J., Jeong, H. S., Kim, D. J., Noh, Y. H., Yuk, D. Y., Hong, J. T. Inhibitory effect of citral on NO production by suppression of iNOS expression and NF-B activation in RAW264. 7 cells[J]. Archives of Pharmacal Research, 2008, 31(3): 342-349.
22. Ortiz, M. I., Ramrez-Montiel, M. L., Gonzlez-Garca, M. P., Ponce-Monter, H. A., Casta?eda-Hernndez, G., Cari?o-Corts, R. The combination of naproxen and citral reduces nociception and gastric damage in rats[J]. Archives of pharmacal research, 2010, 33(10): 1691-1697.
23. Nouvian, M., Hotier, L., Claudianos, C., Giurfa, M., Reinhard, J. Appetitive floral odours prevent aggression in honeybees[J]. Nature communications, 2015, 6: 10247.
24. Zelano, C., Bensafi, M., Porter, J., Mainland, J., Johnson, B., Bremner, E., Sobel, N. Attentional modulation in human primary olfactory cortex[J]. Nature neuroscience, 2005, 8(1): 114.
25. Droby, S., Eick, A., Macarisin, D., Cohen, L., Rafael, G., Stange, R., Shapira, R.. Role of citrus volatiles in host recognition, germination and growth of Penicillium digitatum and Penicillium italicum[J]. Postharvest Biology and Technology, 2008, 49(3): 386-396.
26. Wolken W A M, Tramper J, van der Werf M J. Toxicity of terpenes to spores and mycelium of Penicillium digitatum[J]. Biotechnology and bioengineering, 2002, 80(6): 685-690.
27. Fan, F., Tao, N., Jia, L., He, X. Use of citral incorporated in postharvest wax of citrus fruit as a botanical fungicide against Penicillium digitatum[J]. Postharvest Biology and technology, 2014, 90: 52-55.
28. Vincis, R., Gschwend, O., Bhaukaurally, K., Beroud, J., Carleton, A. Dense representation of natural odorants in the mouse olfactory bulb[J]. Nature neuroscience, 2012, 15(4): 537.
29. Dravnieks A. Atlas of Odor Character Profiles (Philadelphia: ASTM)[J]. 1985.
30. Anderson, A. K., Christoff, K., Stappen, I., Panitz, D., Ghahremani, D. G., Glover, G., Sobel, N. Dissociated neural representations of intensity and valence in human olfaction[J]. Nature neuroscience, 2003, 6(2): 196.
31. Nizampatnam, S., Saha, D., Chandak, R., Raman, B. Dynamic contrast enhancement and flexible odor codes[J]. Nature communications, 2018, 9(1): 3062.
32. National Toxicology Program. NTP toxicology and carcinogenesiss studies of citral (microencapsulated)(CAS No. 5392-40-5) in F344/N rats and B6C3F1 mice (feed studies)[J]. National Toxicology Program technical report series, 2003 (505): 1.
33. Ress, N. B., Hailey, J. R., Maronpot, R. R., Bucher, J. R., Travlos, G. S., Haseman, J. K., Hejtmancik, M. R.. Toxicology and carcinogenesis studies of microencapsulated citral in rats and mice[J]. Toxicological Sciences, 2003, 71(2): 198-206.
34. Dudai, N., Weinstein, Y., Krup, M., Rabinski, T., Ofir, R. Citral is a new inducer of caspase-3 in tumor cell lines[J]. Planta medica, 2005, 71(05): 484-488.
35. Connor M J. Modulation of tumor promotion in mouse skin by the food additive citral (3, 7-dimethyl-2, 6-octadienal)[J]. Cancer letters, 1991, 56(1): 25-28.
36. Xia, H., Liang, W., Song, Q., Chen, X., Chen, X., Hong, J. The in vitro study of apoptosis in NB4 cell induced by citral[J]. Cytotechnology, 2013, 65(1): 49-57.
37. Chaouki, W., Leger, D. Y., Liagre, B., Beneytout, J. L., Hmamouchi, M. Citral inhibits cell proliferation and induces apoptosis and cell cycle arrest in MCF\7 cells[J]. Fundamental & clinical pharmacology, 2009, 23(5): 549-556.
38. Kapur, A., Felder, M., Fass, L., Kaur, J., Czarnecki, A., Rathi, K., Whelan, R. J. Modulation of oxidative stress and subsequent induction of apoptosis and endoplasmic reticulum stress allows citral to decrease cancer cell proliferation[J]. Scientific reports, 2016, 6: 27530.
39. Kermen, F., Chakirian, A., Sezille, C., Joussain, P., Le Goff, G., Ziessel, A., Bensafi, M. Molecular complexity determines the number of olfactory notes and the pleasantness of smells[J]. Scientific reports, 2011, 1: 206.
40. Faraone, N., D'Errico, G., Caleca, V., De Cristofaro, A., & Trimble, R. M. Electrophysiological and behavioral responses of oriental fruit moth to the monoterpenoid citral alone and in combination with sex pheromone[J]. Environmental entomology, 2013, 42(2): 314-322.
41. Wang F, Deng J, Schal C, et al. Non-host plant volatiles disrupt sex pheromone communication in a specialist herbivore[J]. Scientific reports, 2016, 6: 32666.
42. Howard, J. D., Plailly, J., Grueschow, M., Haynes, J. D., Gottfried, J. A. Odor quality coding and categorization in human posterior piriform cortex[J]. Nature neuroscience, 2009, 12(7): 932.
43. Belluscio, L., Lodovichi, C., Feinstein, P., Mombaerts, P., Katz, L. C. Odorant receptors instruct functional circuitry in the mouse olfactory bulb[J]. Nature, 2002, 419(6904): 296.
44. Boschat, C., Plofi, C., Randin, O., Roppolo, D., Lscher, C., Broillet, M. C., Rodriguez, I. Pheromone detection mediated by a V1r vomeronasal receptor[J]. Nature neuroscience, 2002, 5(12): 1261.
45. Tanaka, K., Uda, Y., Ono, Y., Nakagawa, T., Suwa, M., Yamaoka, R., Touhara, K.. Highly selective tuning of a silkworm olfactory receptor to a key mulberry leaf volatile[J]. Current Biology, 2009, 19(11): 881-890.
46. Liu, Z., Wang, X., Lei, C., Zhu, F. Sensory genes identification with head transcriptome of the migratory armyworm, Mythimna separata[J]. Scientific reports, 2017, 7: 46033.
47. Zhang R, Gao G, Chen H. Silencing of the olfactory co-receptor gene in Dendroctonus armandi leads to EAG response declining to major host volatiles[J]. Scientific reports, 2016, 6: 23136.
48. Stotz, S. C., Vriens, J., Martyn, D., Clardy, J., Clapham, D. E. Citral sensing by transient receptor potential channels in dorsal root ganglion neurons[J]. PLoS One, 2008, 3(5): e2082.