2D Structure

3D Structure

β-Caryophyllene


Properties
PID PID00072
Mol. Weight 204.357 g/mol
LogP 4.52
Water solubility less than 1 mg/mL at 70° F (NTP, 1992)
Hydrogen Bond Donor 0
Hydrogen Bond Acceptor 0
Rotatable Bonds 0
XLogP3 4.4

β-Caryophyllene

Identifiers
Formula C15H24
PubChem CID 5281515
FEMA 2252
Flavor Profile Fried, Spice, Wood
Smiles C=C1CCC=C(C)CC[C@@H]2[C@@H]1CC2(C)C
InChl Key NPNUFJAVOOONJE-GFUGXAQUSA-N
InChl InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1
CAS Registry Number 87-44-5
IUPAC Systematic Name (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

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/)


Related Pungent TCM

English Name Pinyin Name (Chinese Name) Latin Name Properties in TCM merdians View Graph
Dryobalanops aromaticaBing Pian(冰片)BorneolMinor cold,Pungent,BitterLung,Spleen,HeartView Graph
Fructus Xanthii sibiriciCang Er Zi(苍耳子)fruit of Siberian CockleblurWarm,Pungent,BitterLung,Spleen,LiverView Graph
Chinese Thorowax Equivalent plant: Bupleurum scorzChai Hu(柴胡)Bupleuri RadixMinor cold, Pungent, BitterLiver, Gallbladder, LungView Graph
Motherwort FruitChong Wei Zi(茺蔚子)Leonuri FructusCold, Bitter, PungentBladder, Spleen, Liver,StomachView Graph
Zedoray RhizomeE Zhu (莪术)Curcumae RhizomaWarm, Pungent, BitterSpleen, LiverView Graph
Chinese Ligusticum Equivalent plant: Ligusticum jeGao Ben (藁本)Ligustici Rhizoma Et RadixWarm, PungentLung, Spleen, StomachView Graph
SafflowerHong Hua (红花)Carthami FlosWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Bunge Pricklyash Equivalent plant: Zanthoxylum schHua Jiao (花椒)Zanthoxyli PericarpiumWarm,PungentSpleen, Stomach, Kidney, LungView Graph
Common Turmeric Equivalent plant: Curcuma aromatiJiang Huang (姜黄)Curcumae Longae RhizomaWarm, Pungent, BitterSpleen, LiverView Graph
Fineleaf SchizonepetaJing Jie (荆芥)Schizonepetae HerbaMinor Warm, PungentLung, LiverView Graph
Frankincense, OlibanumRu Xiang (乳香)OlibanumWarm,Bitter, PungentSpleen, LungView Graph
Wilson CitronXiang Yuan(香橼)Citri FructusWarm, Pungent, Sour, Slightly BitterLung, Spleen, LiverView Graph
Leonurus heterophyllus [Syn. Leonurus artemisia]Yi Mu Cao(益母草)Wormwood-like Motherwort Equivalent plant: LeonuruMinor cold,Pungent,BitterLung,Spleen,HeartView Graph
Virgate Wormwood HerbYin Chen(茵陈)Artemisiae Scopariae HerbaCold, Bitter, pungentBladder, Spleen, Liver, StomachView Graph
Apple MintYu Xian Cao(鱼腥草)Houttuyniae HerbaCold, PungentLungView Graph
Perilia FruitZi Su Zi (紫苏子)Perillae FructusWarm, PungentLung, Spleen, StomachView Graph
Cablin PotchouliGuang Huo Xiang (广藿香)Pogostemonis HerbaMinor Warm,PungentLung, Spleen, StomachView Graph
Fresh Common GingerSheng Jiang (生姜)Zingiber Rhizoma RecensWarm, PungentLung, Spleen, StomachView Graph
Chinese Angelica Equivalent plant: PhlojodicarpusDang Gui (当归)Angelicae Sinensis RadixWarm,Pungent,SweetSpleen,Liver,HeartView Graph
Oriental Sweetgum ResinSu He Xiang (苏合香)StyraxWarm, PungentLung, Spleen, StomachView Graph
Lily Magnolia Buds Equivalent plant: Magnolia liliXin Yi (辛夷)Magnoliae FlosWarm, PungentLung, Spleen, StomachView Graph
Perilla frutescens var. argutaZi Su(紫苏叶)Common Perilla Equivalent plant: Perilla frutescenWarm, PungentLung, Spleen, StomachView Graph
Murraya paniculata [Syn. Chalcas paniculata]Jiu Li Xiang(九里香)Common Jasminorange Equivalent plant: Murraya panNeural, Bitter, PungentLungView Graph
Dryobalanops aromaticaBing Pian(冰片)BorneolMinor cold,Pungent,BitterLung,Spleen,HeartView Graph
Fructus Xanthii sibiriciCang Er Zi(苍耳子)fruit of Siberian CockleblurWarm,Pungent,BitterLung,Spleen,LiverView Graph

Pharmacological action

Caryophyllene or (-)--caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, rosemary, and hops.

-Caryophyllene (BCP) is an important cannabinoid originated from the essential oils of different species, such as Cinnamomum spp., Piper nigrum and Cannabis sativa. As a natural bicyclic sesquiterpene, BCP has been reported to serve as a full agonist of cannabinoid receptor type 2 (CB2R) by a selective binding. -Caryophyllene (BCP), an important cannabinoid derived from the essential oils of different species, has displayed pharmacological properties in different kinds of tissues and cells. -Caryophyllene is a major volatile compound found in large quantities in the essential oil of Cannabis sativa L. (up to 35%)

Beta-Caryophyllene 1 is a sesquiterpene present in natural products e.g. the oil of cloves, cinnamon leaves and copaiba balsam, all of which have been used as natural remedies and as fragrances. The odour of b-caryophyllene, is described as woody and spicy. Beta-caryophyllene is an unsaturated hydrocarbon it can be expected to autoxidize when air exposed. -Caryophyllene is a sesquiterpene which is commonly used as fragrance chemical because of its pleasant odour.

-caryophyllene is a major component from the essential oil of Alpinia purpurata. betacaryophyllene (-caryophyllene) is a natural sesquiterpene present in many plant essential oils, such as Achyrocline satureioides, being a major component of some traditional medicinal herbs. Also in this case, -caryophyllene is one of the major chemical components of this essential oil.

Beta-Caryophyllene (BCP) is a sesquiterpene that binds to the cannabinoid 2 (CB2) receptor and exerts anti-inflammatory effects. b-Caryophyllene (BCP) is a natural sesquiterpene found in essential oils from a variety of plant species, including medicinal plants (e.g., cinnamon, origanum, black pepper, and marijuana).

-Caryophyllene (b-Car) is a natural antioxidant. It is Cannabis-derived cannabinoid receptors type 2 (CB2R) agonist.



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.

References

1. https://en.wikipedia.org/wiki/Caryophyllene

2. de Morais Oliveira-Tintino C D, Pessoa R T, Fernandes M N M, et al. Anti-inflammatory and anti-edematogenic action of the Croton campestris A. St.-Hil (Euphorbiaceae) essential oil and the compound -caryophyllene in in vivo models[J]. Phytomedicine, 2018, 41: 82-95.

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5. Galdino, P. M., Nascimento, M. V. M., Florentino, I. F., Lino, R. C., Fajemiroye, J. O., Chaibub, B. A., Costa, E. A.. The anxiolytic-like effect of an essential oil derived from Spiranthera odoratissima A. St. Hil. leaves and its major component, -caryophyllene, in male mice[J]. Progress in Neuro-Psychopharmacology and Biological Psychiatry, 2012, 38(2): 276-284.

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11. Calleja, M. A., Vieites, J. M., Montero-Meterdez, T., Torres, M. I., Faus, M. J., Gil, A., Surez, A. The antioxidant effect of -caryophyllene protects rat liver from carbon tetrachloride-induced fibrosis by inhibiting hepatic stellate cell activation[J]. British journal of nutrition, 2013, 109(3): 394-401.

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18. Ashitani, T., Kusumoto, N., Borg-Karlson, A. K., Fujita, K., Takahashi, K. Antitermite activity of -caryophyllene epoxide and episulfide[J]. Zeitschrift fr Naturforschung C, 2013, 68(7-8): 302-306.

19. Assis, L. C., Straliotto, M. R., Engel, D., Hort, M. A., Dutra, R. C., De Bem, A. F. -Caryophyllene protects the C6 glioma cells against glutamate-induced excitotoxicity through the Nrf2 pathway[J]. Neuroscience, 2014, 279: 220-231.

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21. Al Mansouri, S., Ojha, S., Al Maamari, E., Al Ameri, M., Nurulain, S. M., Bahi, A. The cannabinoid receptor 2 agonist, -caryophyllene, reduced voluntary alcohol intake and attenuated ethanol-induced place preference and sensitivity in mice[J]. Pharmacology Biochemistry and Behavior, 2014, 124: 260-268.

22. Lou, J., Cao, G., Li, R., Liu, J., Dong, Z., Xu, L. -Caryophyllene attenuates focal cerebral ischemia-reperfusion injury by Nrf2/HO-1 pathway in rats[J]. Neurochemical research, 2016, 41(6): 1291-1304.

23. Bento, A. F., Marcon, R., Dutra, R. C., Claudino, R. F., Cola, M., Leite, D. F. P., Calixto, J. B. -Caryophyllene inhibits dextran sulfate sodium-induced colitis in mice through CB2 receptor activation and PPAR pathway[J]. The American journal of pathology, 2011, 178(3): 1153-1166.

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25. Paula-Freire, L. I. G. D., Andersen, M. L., Gama, V. S., Molska, G. R., Carlini, E. L. A. The oral administration of trans-caryophyllene attenuates acute and chronic pain in mice[J]. Phytomedicine, 2014, 21(3): 356-362.

26. Galdino, P. M., Nascimento, M. V. M., Florentino, I. F., Lino, R. C., Fajemiroye, J. O., Chaibub, B. A., Costa, E. A. The anxiolytic-like effect of an essential oil derived from Spiranthera odoratissima A. St. Hil. leaves and its major component, -caryophyllene, in male mice[J]. Progress in Neuro-Psychopharmacology and Biological Psychiatry, 2012, 38(2): 276-284.

27. Kim, C., Cho, S. K., Kim, K. D., Nam, D., Chung, W. S., Jang, H. J., Ahn, K. S. -Caryophyllene oxide potentiates TNF-induced apoptosis and inhibits invasion through down-modulation of NF-B-regulated gene products[J]. Apoptosis, 2014, 19(4): 708-718.

28. Calleja, M. A., Vieites, J. M., Montero-Meterdez, T., Torres, M. I., Faus, M. J., Gil, A., Surez, A. The antioxidant effect of -caryophyllene protects rat liver from carbon tetrachloride-induced fibrosis by inhibiting hepatic stellate cell activation[J]. British journal of nutrition, 2013, 109(3): 394-401.

29. Liu, H., Song, Z., Liao, D., Zhang, T., Liu, F., Zhuang, K., Yang, L. Neuroprotective effects of trans-caryophyllene against kainic acid induced seizure activity and oxidative stress in mice[J]. Neurochemical research, 2015, 40(1): 118-123.

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49. Horvth, B., Mukhopadhyay, P., Kechrid, M., Patel, V., Tanchian, G., Wink, D. A., Pacher, P. -Caryophyllene ameliorates cisplatin-induced nephrotoxicity in a cannabinoid 2 receptor-dependent manner[J]. Free Radical Biology and Medicine, 2012, 52(8): 1325-1333.

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55. Cho, H. I., Hong, J. M., Choi, J. W., Choi, H. S., Kwak, J. H., Lee, D. U., Lee, S. M. -Caryophyllene alleviates d-galactosamine and lipopolysaccharide-induced hepatic injury through suppression of the TLR4 and RAGE signaling pathways[J]. European journal of pharmacology, 2015, 764: 613-621.

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60. http://realbeer.com/hops/aroma.html