2D Structure
3D Structure
| Properties | |
|---|---|
| PID | PID00071 |
| Mol. Weight | 204.357 g/mol |
| LogP | 4.52 |
| Water solubility | 0.0000141 mol/L at 20 °C |
| Hydrogen Bond Donor | 0 |
| Hydrogen Bond Acceptor | 0 |
| Rotatable Bonds | 1 |
| XLogP3-AA | 5.2 |
| Identifiers | |
|---|---|
| Formula | C15H24 |
| PubChem CID | 9855795 |
| FEMA | 3443 |
| Flavor Profile | Citrus, Green, Oil, Wood |
| Smiles | C=C(C)[C@@H]1CCC2=CCC[C@@H](C)[C@]2(C)C1 |
| InChl Key | QEBNYNLSCGVZOH-NFAWXSAZSA-N |
| InChl | InChI=1S/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h7,12-13H,1,5-6,8-10H2,2-4H3/t12-,13-,15+/m1/s1 |
| CAS Registry Number | 4630-07-3 |
| IUPAC Systematic Name | (3R,4aS,5R)-4a,5-dimethyl-3-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene |
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 |
|---|---|---|---|---|---|
| Long Pepper | Bi Ba (荜茇) | Piperis Longi Fructus | Hot,Pungent | Large Intestine, Stomach | View Graph |
| Chinese Thorowax Equivalent plant: Bupleurum scorz | Chai Hu(柴胡) | Bupleuri Radix | Minor cold, Pungent, Bitter | Liver, Gallbladder, Lung | View Graph |
| Aquilaria agallocha | Chen Xiang(沉香) | Eaglewood Equivalent plant: Aquilaria sinensis | Warm,Pungent,Bitter | Lung,Spleen,Liver | View Graph |
| Lesser Galangal | Gao Liang Jiang (高良姜) | Alpiniae Officinarum Rhizoma | Hot,Pungent | Large Intestine, Stomach | View Graph |
| Cablin Potchouli | Guang Huo Xiang (广藿香) | Pogostemonis Herba | Minor Warm,Pungent | Lung, Spleen, Stomach | View Graph |
| bark of Officinal magnolia | Hou Pu(厚朴) | Magnoliae Officinalis Cortex | Warm, Pungent, Bitter | Spleen, Liver | View Graph |
| Dahurian Rhododendron | Man Shan Hong (满山红) | Rhododendri Daurici Folium | Cold, Pungent, Bitter | Liver, Heart, Lung | View Graph |
| Fresh Common Ginger | Sheng Jiang (生姜) | Zingiber Rhizoma Recens | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Combined Spicebush | Wu Yao(乌药) | Linderae Radix | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Siebold Wildginger Equivalent plant: Asarum hetero | Xi Xin (细辛) | Asari Radix Et Rhizoma | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Common Goldenrod | Yi Zhi Huang Hua(一枝黄花) | Solidaginis Herba | Cool, Bitter, Pungent | Liver, Lung | View Graph |
| Sharpleaf Galangal | Yi Zhi (益智) | Fritillariae Thunbergii Bulbus | Warm, Pungent, | Stomach | View Graph |
Valencene is a sesquiterpene that is an aroma component of citrus fruit and citrus-derived odorants.
Valencene is natural flavors and fragrances, these essential oils have been widely used in the food, chemical, cosmetic and pharmaceutical industries. Valencene are natural flavors and fragrances, these essential oils have been widely used in the food, chemical, cosmetic and pharmaceutical industries. Valencene is the main constituent of orange (Citrus sinensis) peel oil. Chemical oxidation of valencene requires the use of tert-butyl chromate.For plants, several cytochrome P450 enzymes capable of oxidising valencene have been described. The bicyclic sesquiterpene (+)-valencene is a main component of the essential oil of Valencia oranges (Citrus sinensis).
Valencene is also a chemical precursor to nootkatone, a grapefruit flavor ingredient. Valencene has proved tricky to make chemically, so valencene buyers have historically depended on orange extracts, the supply and pricing of which has been disrupted by weather events such as Hurricane Andrew and diseases
such as citrus greening.
Valencene is reported to occur in the following foods* and is found in some natural complex substances (NCS):
Annatto (Bixa orellana L.) Artichoke Cardamom (Ellettaria cardamomum Maton.) Celery (Apium graveolens L.) Citrus fruits Cloves (Eugenia caryophyllata Thunberg) Cocoa Date (Phoenix dactylifera L.) Hop (Humulus lupulus) Macadamia nut (Macadamia integrifolia) Mangifera species Mangosteen (Garcinia mangostana L.) Mastic (Pistacia lentiscus) Olive (Olea europaea) Thyme (Thymus species).
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/Valencene
2. Tsoyi, K., Jang, H. J., Lee, Y. S., Kim, Y. M., Kim, H. J., Seo, H. G., Chang, K. C. (+)-Nootkatone and (+)-valencene from rhizomes of Cyperus rotundus increase survival rates in septic mice due to heme oxygenase-1 induction. Journal of ethnopharmacology 137.3 (2011): 1311-1317.
3. Cankar K, van Houwelingen A, Goedbloed M, et al. Valencene oxidase CYP706M1 from Alaska cedar (Callitropsis nootkatensis)[J]. FEBS letters, 2014, 588(6): 1001-1007.
4. Gupta, M. B., Palit, T. K., Singh, N., Bhargava, K. P. Pharmacological studies to isolate the active constituents from Cyperus rotundus possessing anti-inflammatory, anti-pyretic and analgesic activities[J]. The Indian journal of medical research, 1971, 59(1): 76.
5. Seo, E. J., Lee, D. U., Kwak, J. H., Lee, S. M., Kim, Y. S., Jung, Y. S. Antiplatelet effects of Cyperus rotundus and its component (+)-nootkatone[J]. Journal of ethnopharmacology, 2011, 135(1): 48-54.
6. Hunter G L K, Brogden Jr W B. Conversion of valencene to nootkatone[J]. Journal of Food Science, 1965, 30(5): 876-878.
7. Sharon\Asa, L., Shalit, M., Frydman, A., Bar, E., Holland, D., Or, E., Eyal, Y. Citrus fruit flavor and aroma biosynthesis: isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene[J]. The Plant Journal, 2003, 36(5): 664-674.
8. Cankar, K., van Houwelingen, A., Bosch, D., Sonke, T., Bouwmeester, H., Beekwilder, J. A chicory cytochrome P450 mono\oxygenase CYP71AV8 for the oxidation of (+)\valencene[J]. FEBS letters, 2011, 585(1): 178-182.
9. Fraatz, M. A., Riemer, S. J., St?ber, R., Kaspera, R., Nimtz, M., Berger, R. G., Zorn, H. A novel oxygenase from Pleurotus sapidus transforms valencene to nootkatone[J]. Journal of Molecular Catalysis B: Enzymatic, 2009, 61(3-4): 202-207.
10. Zhou, K., Qiao, K., Edgar, S., Stephanopoulos, G. Distributing a metabolic pathway among a microbial consortium enhances production of natural products[J]. Nature biotechnology, 2015, 33(4): 377.
11. Waltz E. Engineers of scent[J]. 2015.
12. Vinholes, J., Rudnitskaya, A., Gon?alves, P., Martel, F., Coimbra, M. A., Rocha, S. M. Hepatoprotection of sesquiterpenoids: a quantitative structureCactivity relationship (QSAR) approach[J]. Food chemistry, 2014, 146: 78-84.
13. Liu, K., Chen, Q., Liu, Y., Zhou, X., Wang, X. Isolation and biological activities of decanal, linalool, valencene, and octanal from sweet orange oil[J]. Journal of food science, 2012, 77(11): C1156-C1161.
14. Castillo-Araiza, C. O., Palmern-Carre?o, D., Prado-Barragn, A., Huerta-Ochoa, S. On the conceptual design of a partitioning technology for the bioconversion of (+)-valencene to (+)-nootkatone on whole cells: Experimentation and modelling[J]. Chemical Engineering and Processing: Process Intensification, 2017, 122: 493-507.
15. Api AM?,?Belsito D?,?Botelho D. RIFM fragrance ingredient safety assessment, Valencene, CAS Registry Number 4630-07-3[J]. Food & Chemical Toxicology, 2018, 118: S141CS146
16. Elston A, Lin J, Rouseff R. Determination of the role of valencene in orange oil as a direct contributor to aroma quality[J]. Flavour and fragrance journal, 2005, 20(4): 381-386.
17. Palmern-Carre?o, D. M., Rutiaga-Qui?ones, O. M., Calvo, J. V., Prado-Barragn, A., Huerta-Ochoa, S. Screening of microorganisms for bioconversion of (+)-valencene to (+)-nootkatone[J]. LWT-Food Science and Technology, 2015, 64(2): 788-793.
18. Cankar, K., van Houwelingen, A., Goedbloed, M., Renirie, R., de Jong, R. M., Bouwmeester, H., Beekwilder, J. Valencene oxidase CYP706M1 from Alaska cedar (Callitropsis nootkatensis)[J]. FEBS letters, 2014, 588(6): 1001-1007.
19. Cankar, K., van Houwelingen, A., Goedbloed, M., Renirie, R., de Jong, R. M., Bouwmeester, H., Beekwilder, J. Valencene oxidase CYP706M1 from Alaska cedar (Callitropsis nootkatensis)[J]. FEBS letters, 2014, 588(6): 1001-1007.
20. Gavira, C., H?fer, R., Lesot, A., Lambert, F., Zucca, J., Werck-Reichhart, D. Challenges and pitfalls of P450-dependent (+)-valencene bioconversion by Saccharomyces cerevisiae[J]. Metabolic engineering, 2013, 18: 25-35.
21. Girhard, M., Machida, K., Itoh, M., Schmid, R. D., Arisawa, A., Urlacher, V. B. Regioselective biooxidation of (+)-valencene by recombinant E. coli expressing CYP109B1 from Bacillus subtilis in a two-liquid-phase system[J]. Microbial cell factories, 2009, 8(1): 36.
22. Leonhardt, R. H., Plagemann, I., Linke, D., Zelena, K., Berger, R. G. Orthologous lipoxygenases of Pleurotus spp.CA comparison of substrate specificity and sequence homology[J]. Journal of Molecular Catalysis B: Enzymatic, 2013, 97: 189-195.
23. Guo, X., Sun, J., Li, D., & Lu, W. Heterologous biosynthesis of (+)-nootkatone in unconventional yeast Yarrowia lipolytica[J]. Biochemical Engineering Journal, 2018.
24. Bicas, J. L., de Quadros, C. P., Nri-Numa, I. A., & Pastore, G. M. Integrated process for co-production of alkaline lipase and R-(+)--terpineol by Fusarium oxysporum[J]. Food chemistry, 2010, 120(2): 452-456.