2D Structure
3D Structure
| Properties | |
|---|---|
| PID | PID00062 |
| Mol. Weight | 136.238 g/mol |
| LogP | 3.21 |
| Water solubility | 0.000977 mol/L at 20 °C |
| Hydrogen Bond Donor | 0 |
| Hydrogen Bond Acceptor | 0 |
| Rotatable Bonds | 1 |
| XLogP3-AA | 3.2 |
| Identifiers | |
|---|---|
| Formula | C10H16 |
| PubChem CID | 7460 |
| FEMA | 2856 |
| Flavor Profile | Citrus, Fresh, Mint, Pepper, Spice, Wood |
| Smiles | CC1=CCC(C(C)C)C=C1 |
| InChl Key | OGLDWXZKYODSOB-UHFFFAOYSA-N |
| InChl | InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3 |
| CAS Registry Number | 99-83-2, 1329-99-3, 4221-98-1, 34448-33-4 |
| IUPAC Systematic Name | 2-methyl-5-propan-2-ylcyclohexa-1,3-diene |
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 |
|---|---|---|---|---|---|
| Common Ginger Dried Rhizome | Gan Jiang (干姜) | Zingiberis Rhizoma | Hot, Pungent | Lung, Spleen, Stomach, Heart, Kidney | View Graph |
| Dahurian Angelica | Bai Zhi(白芷) | Angelicae Dahuricae Radix | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Bunge Pricklyash Equivalent plant: Zanthoxylum sch | Hua Jiao (花椒) | Zanthoxyli Pericarpium | Warm,Pungent | Spleen, Stomach, Kidney, Lung | View Graph |
| Lily Magnolia Buds Equivalent plant: Magnolia lili | Xin Yi (辛夷) | Magnoliae Flos | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Fortune Eupatorium Equivalent plant: Eupatorium f | Pei Lan(佩兰) | Eupatorii Herba | Neural, 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 |
| Villous Amomum Equivalent plant: Amomum xanthioide | Sha Ren (砂仁) | Amomi Fructus | Warm, Pungent | Lung, Spleen, Stomach | View Graph |
| Frankincense, Olibanum | Ru Xiang (乳香) | Olibanum | Warm，Bitter, Pungent | Spleen, Lung | View Graph |
| Wilson Citron | Xiang Yuan(香橼) | Citri Fructus | Warm, Pungent, Sour, Slightly Bitter | Lung, Spleen, Liver | View Graph |
Alpha-Phellandrene (5-isopropyl-2-methyl-1,3-cyclohexadiene) is a cyclic monoterpene found in the essential oils of several plants, such as Schinus terebinthifolius Raddi (15.7%), Solanum erianthum D. Don (17.5%), Thymus kotschyanus Boiss and Hohen (10.8%), Cupressus atlantica Gaussen (5.5%), Anethum graveolens L. (32%), and Myrica gale L. (8%).
Alpha-Phellandrene and Nonanal are present in large quantities in many species such as canola, soybean, Senecio laetus, Haplophyllum tuberculatum, Minuartia meyeri and Apium graveolens.
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. Opdyke D L J. -Phellandrene[J]. Food Cosmet Toxicol, 1978, 16: 843-844.
2. Foss S, Heyen U, Harder J. Alcaligenes defragrans sp. nov., description of four strains isolated on alkenoic monoterpenes ((+)-menthene, -pinene, 2-carene, and -phellandrene) and nitrate[J]. Systematic and applied microbiology, 1998, 21(2): 237-244.
3. Demirci, F., Kirimer, N., Demirc, B., Noma, Y., Ba?era, K. H. C. Screening of biotransformation products of carvone enantiomers by headspace-SPME/GC-MS[J]. Zeitschrift fr Naturforschung C, 2001, 56(1-2): 58-64.
4. ??can, G., K?r?mer, N., Demirci, F., Demirci, B., Noma, Y., Ba?er, K. H. C. Biotransformation of (?)\(R)\\Phellandrene: Antimicrobial Activity of Its Major Metabolite[J]. Chemistry & biodiversity, 2012, 9(8): 1525-1532.
5. Costa, T. R., Fernandes, O. F., Santos, S. C., Oliveira, C. M., Li?o, L. M., Ferri, P. H., Maria do Rosrio, R. S. Antifungal activity of volatile constituents of Eugenia dysenterica leaf oil[J]. Journal of ethnopharmacology, 2000, 72(1-2): 111-117.
6. Inouye S, Takizawa T, Yamaguchi H. Antibacterial activity of essential oils and their major constituents against respiratory tract pathogens by gaseous contact[J]. Journal of antimicrobial chemotherapy, 2001, 47(5): 565-573.
7. Fernando, W. D., Ramarathnam, R., Krishnamoorthy, A. S., Savchuk, S. C. Identification and use of potential bacterial organic antifungal volatiles in biocontrol[J]. Soil Biology and Biochemistry, 2005, 37(5): 955-964.
8. Al-Burtamani, S. K. S., Fatope, M. O., Marwah, R. G., Onifade, A. K., Al-Saidi, S. H. Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman[J]. Journal of ethnopharmacology, 2005, 96(1-2): 107-112.
9. Yayli, N., Glec, C., ?nc, O., Ya?ar, A., lker, S., Co?kun?elebi, K., Terzio?lu, S. Composition and antimicrobial activities of volatile components of Minuartia meyeri[J]. Turkish Journal of Chemistry, 2006, 30(1): 71-76.
10. Rodriguez-Burbano D, Quijano-Celis C E, Pino J A. Composition of the essential oil from leaves of Astronium graveolens Jacq grown in Colombia[J]. Journal of Essential Oil Research, 2010, 22(6): 488-489.
11. Hernndez, V., Mora, F., Araque, M., De Montijo, S., Rojas, L., Melndez, P., De Tommasi, N. Chemical composition and antibacterial activity of Astronium graveolens JACQ essential oil[J]. Revista latinoamericana de qumica, 2013, 41(2): 89-94.
12. Pandey, A. K., Mohan, M., Singh, P., Palni, U. T., Tripathi, N. N. Chemical composition, antibacterial and antioxidant activity of essential oil of Eupatorium adenophorum Spreng. from Eastern Uttar Pradesh, India[J]. Food Bioscience, 2014, 7: 80-87.
13. Zhang, J. H., Sun, H. L., Chen, S. Y., Zeng, L., Wang, T. T. Anti-fungal activity, mechanism studies on -Phellandrene and Nonanal against Penicillium cyclopium[J]. Botanical studies, 2017, 58(1): 13.
14. Evergetis E, Michaelakis A, Haroutounian S A. Exploitation of Apiaceae family essential oils as potent biopesticides and rich source of phellandrenes[J]. Industrial Crops and Products, 2013, 41: 365-370.
15. Siqueira, H. D. A. S., Neto, B. S., Sousa, D. P., Gomes, B. S., da Silva, F. V., Cunha, F. V., Ribeiro, R. A. -Phellandrene, a cyclic monoterpene, attenuates inflammatory response through neutrophil migration inhibition and mast cell degranulation[J]. Life sciences, 2016, 160: 27-33.
16. Lima, D. F., Brand?o, M. S., Moura, J. B., Leit?o, J. M., Carvalho, F. A., Mira, L. M., Almeida, F. R. Antinociceptive activity of the monoterpene \phellandrene in rodents: possible mechanisms of action[J]. Journal of Pharmacy and Pharmacology, 2012, 64(2): 283-292.
17. https://en.m.wikipedia.org/wiki/Phellandrene
18. Jacobs S W L, Pickard J. Plants of New South Wales: a census of the cycads, conifers and angiosperms[J]. Sydney: National Herbarium of New South Wales 226p.-maps.. En Maps. Geog, 1981, 7.
19. Ramos, C. S. Essential oil composition and acaricidal activity of Schinus terebinthifolius from Atlantic Forest of Pernambuco, Brazil against Tetranychus urticae.Natural product communications 7.1 (2012): 129-132.
20. Essien, E. E., Ogunwande, I. A., Setzer, W. N., & Ekundayo, O. Chemical composition, antimicrobial, and cytotoxicity studies on S. erianthum and S. macranthum essential oils. Pharmaceutical biology 50.4 (2012): 474-480.
21. Asbaghian, S., Shafaghat, A., Zarea, K., Kasimov, F., & Salimi, F. Comparison of volatile constituents, and antioxidant and antibacterial activities of the essential oils of Thymus caucasicus, T. kotschyanus and T. vulgaris. Natural product communications 6.1 (2011): 137-140.
22. Arjouni, M. Y., Bahri, F., Romane, A., & El, M. F. Chemical composition and antimicrobial activity of essential oil of Cupressus atlantica. Natural product communications 6.10 (2011): 1519-1522.
23. Hajhashemi, Valiollah, and Naser Abbasi. Hypolipidemic activity of Anethum graveolens in rats. Phytotherapy Research: An International Journal Devoted to Pharmacological and Toxicological Evaluation of Natural Product Derivatives 22.3 (2008): 372-375.
24. Popovici, J., Bertrand, C., Bagnarol, E., Fernandez, M. P., Comte, G. Chemical composition of essential oil and headspace-solid microextracts from fruits of Myrica gale L. and antifungal activity." Natural product research 22.12 (2008): 1024-1032.
25. Erazo, S., Delporte, C., Negrete, R., Garca, R., Zaldvar, M., Iturra, G., Backhouse, N. Constituents and biological activities of Schinus polygamus[J]. Journal of ethnopharmacology, 2006, 107(3): 395-400.
26. Vendruscolo, A., Takaki, I., Bersani-Amado, L. E., Dantas, J. A., Bersani-Amado, C. A., Cuman, R. K. Antiinflammatory and antinociceptive activities of zingiber officinale roscoe essential oil in experimental animal models[J]. Indian Journal of Pharmacology, 2006, 38(1): 58.