2D Structure
3D Structure
| Properties | |
|---|---|
| PID | PID00141 |
| Mol. Weight | 190.286 g/mol |
| LogP | 3.68 |
| Water solubility | 0.001 mol/L at 20 °C |
| Hydrogen Bond Donor | None |
| Hydrogen Bond Acceptor | None |
| Rotatable Bonds | None |
| XLogP3-AA | 3.2 |
| Identifiers | |
|---|---|
| Formula | C13H18O |
| PubChem CID | 5366074 |
| FEMA | 3420 |
| Flavor Profile | Floral |
| Smiles | C/C=C/C(=O)C1=C(C)C=CCC1(C)C |
| InChl Key | POIARNZEYGURDG-FNORWQNLSA-N |
| InChl | InChI=1S/C13H18O/c1-5-7-11(14)12-10(2)8-6-9-13(12,3)4/h5-8H,9H2,1-4H3/b7-5+ |
| CAS Registry Number | 23726-93-4, 23696-85-7 |
| IUPAC Systematic Name | (E)-1-(2,6,6-trimethylcyclohexa-1,3-dien-1-yl)but-2-en-1-one |
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 |
|---|---|---|---|---|---|
| Eucommia ulmoides | Du Zhong Ye(杜仲叶) | Eucommia Leaf | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
| Chinese Ephedra Equivalent plant: Ephedra equiseti | Ma Huang (麻黄) | Ephedrae Herba | Warm, Pungent, Slightly Bitter | Lung, Bladder | View Graph |
| Bugbane Equivalent plant: Cimicifuga dahurica, Ci | Sheng Ma(升麻) | Cimicifugae Rhizoma | Cold, Sweet, Pungent | Lung, Spleen, Large Intestine, Stomach | View Graph |
| Paniculate Swallowwort | Xu Chang Qing(徐长卿) | Cynanchi Paniculati Radix Et Rhizoma | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Shorthorned Epimedium Equivalent plant: Epimedium | Yin Yang Huo (淫羊藿) | Epimedii Folium | Warm, Sweet, Pungent | Liver, Kidney | View Graph |
Damascenones are a series of closely related chemical compounds that are components of a variety of essential oils. The damascenones belong to a family of
chemicals known as rose ketones, which also includes damascones and ionones. beta-Damascenone is a major contributor to the aroma of roses, despite its
very low concentration, and is an important fragrance chemical used in perfumery.
Damascenone is a fragrance ingredient used in many fragrance compounds. It may be found in fragrances used in decorative cosmetics, fine fragrances,
shampoos, toilet soaps and other toiletries as well as non-cosmetic products such as household cleaners and detergents.
Damascenone is well-known for its potent flavour with an extremely low odour threshold. Damascenone is an example of terpenes found in citrus and other
fruits at low concentrations. Damascenone is a potent flavour compound, possessing an extremely low odour threshold of 0.002 ppb in water.
Damascenone was also determined as one of the most important odour components of Japanese green tea (Sencha) products. Damascenone exhibited the
highest odour potencies after heat processing and is mainly responsible for the sweet flavour of heated black tea.
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/Damascenone
2. Uddin A N , Labuda I , Burns F J . A novel mechanism of filaggrin induction and sunburn prevention by -damascenone in Skh-1 mice[J]. Toxicology & Applied Pharmacology, 2012, 265(3):335-341.
3. Mendes-Pinto, M. M., Silva Ferreira, A. C., Caris-Veyrat, C., Guedes de Pinho, P. Carotenoid, chlorophyll, and chlorophyll-derived compounds in grapes and port wines[J]. Journal of agricultural and food chemistry, 2005, 53(26): 10034-10041.
4. Yang Z, Baldermann S, Watanabe N. Recent studies of the volatile compounds in tea[J]. Food Research International, 2013, 53(2): 585-599.
5. Yang Z, Baldermann S, Watanabe N. Formation of damascenone and its related compounds from carotenoids in tea[J]. Tea in Health and Disease Prevention, 2013: 375-386.
6. Uddin A N, Labuda I, Burns F J. A novel mechanism of filaggrin induction and sunburn prevention by -damascenone in Skh-1 mice[J]. Toxicology and applied pharmacology, 2012, 265(3): 335-341.
7. Wu, Y., Duan, S., Zhao, L., Gao, Z., Luo, M., Song, S., Wang, S. Aroma characterization based on aromatic series analysis in table grapes[J]. Scientific reports, 2016, 6: 31116.
8. Garca-Carpintero E G, Snchez-Palomo E, Gallego M A G, et al. Volatile and sensory characterization of red wines from cv. Moravia Agria minority grape variety cultivated in La Mancha region over five consecutive vintages[J]. Food Research International, 2011, 44(5): 1549-1560.
9. Mahattanatawee, K., Perez-Cacho, P. R., Davenport, T., Rouseff, R. Comparison of three lychee cultivar odor profiles using gas chromatography? olfactometry and gas chromatography? sulfur detection[J]. Journal of agricultural and food chemistry, 2007, 55(5): 1939-1944.
10. Garca\Carpintero E G, Snchez\Palomo E, Gmez Gallego M A, et al. Effect of cofermentation of grape varieties on aroma profiles of La Mancha red wines[J]. Journal of food science, 2011, 76(8): C1169-C1180.
11. Culler, L., Escudero, A., Cacho, J., Ferreira, V. Gas chromatography? olfactometry and chemical quantitative study of the aroma of six premium quality Spanish aged red wines[J]. Journal of Agricultural and Food Chemistry, 2004, 52(6): 1653-1660.
12. Buttery, R. G., Teranishi, R., Ling, L. C., Turnbaugh, J. G. Quantitative and sensory studies on tomato paste volatiles[J]. Journal of Agricultural and Food Chemistry, 1990, 38(1): 336-340.
13. Buttery R G, Teranishi R, Ling L C. Fresh tomato aroma volatiles: a quantitative study[J]. Journal of Agricultural and Food Chemistry, 1987, 35(4): 540-544.
14. Kumazawa K, Masuda H. Identification of potent odorants in Japanese green tea (Sen-cha)[J]. Journal of agricultural and food chemistry, 1999, 47(12): 5169-5172.
15. Kumazawa K, Masuda H. Change in the flavor of black tea drink during heat processing[J]. Journal of agricultural and food chemistry, 2001, 49(7): 3304-3309.
16. Kinoshita, T., Hirata, S., Yang, Z., Baldermann, S., Kitayama, E., Matsumoto, S., Watanabe, N. Formation of damascenone derived from glycosidically bound precursors in green tea infusions[J]. Food chemistry, 2010, 123(3): 601-606.
17. Lapczynski, A., Lalko, J., McGinty, D., Bhatia, S., Letizia, C. S., Api, A. M. Fragrance material review on damascenone[J]. Food and Chemical Toxicology, 2007, 45(1): S172-S178.
18. Puglisi, C. J., Elsey, G. M., Prager, R. H., Skouroumounis, G. K., Sefton, M. A. Identification of a precursor to naturally occurring -damascenone[J]. Tetrahedron Letters, 2001, 42(39): 6937-6939.
19. Demain A L, Martens E. Production of valuable compounds by molds and yeasts[J]. The Journal of antibiotics, 2017, 70(4): 347.
20. Knight, S., Klaere, S., Fedrizzi, B., Goddard, M. R. Regional microbial signatures positively correlate with differential wine phenotypes: evidence for a microbial aspect to terroir[J]. Scientific reports, 2015, 5: 14233.