MOLECULE
β-Caryophyllene
(-)-beta-caryophyllene is a beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. It has a role as an insect attractant, a metabolite, a non-steroidal anti-inflammatory drug and a fragrance. It is an enantiomer of a (+)-beta-caryophyllene.
Summary from ChEBI, via PubChem.
Identity
Chemistry
- Formula
- C15H24
- Molecular weight
- 204.35 g/mol
- IUPAC name
- (1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
- InChIKey
- NPNUFJAVOOONJE-GFUGXAQUSA-N
- SMILES
- CC1=CCCC(=C)C2CC(C2CC1)(C)C
- PubChem
- CID 5281515 ↗
Provenance
Contributing sources
- PubChem
- ChEBI
- LOTUS
Natural occurrence
Found in
- Korean perilla 13
- Sweet wormwood 11
- Hops 9
- Chaste-tree 9
- Wild Celery 8
- R. officinalis 8
- Sage 8
- Wild Carrot 7
- Holy basil 7
- Oregano 7
- Thyme 7
- Common Valerian 7
- C. deliciosa 6
- Mandarin orange 6
- Pignut 6
- Black pepper 6
- Greek oregano 6
- Persian zatar 6
- Wild cinnamon 5
- L. multiflora 5
- African basil 5
- Ginger 5
- C. recutita 4
- Lemonscented gum 4
- C. nepetifolius 4
- Nut-grass 4
- Torch-ginger 4
- L. origanoides 4
- Wild Chamomile 4
- Balm 4
- M. piperita 4
- Myrtle 4
- Sweet basil 4
- Syrian oregano 4
- Guava 4
- T. capitata 4
- T. spicata 4
- Thymus 4
- Shampoo Ginger 4
- Melegueta pepper 3
- Tropical whiteweed 3
- A. chinensis 3
- Greater galangal 3
- Shellplant 3
- A. triangularis 3
- B. pendula 3
- Jack in the bush 3
- Grapefruit 3
- C. unshiu 3
- C. maculata 3
- East Indian lemongrass 3
- H. odoratissimum 3
- Heterotropa 3
- Common Juniper 3
- L. dulcis 3
- Sweet Gum 3
- Pennyroyal 3
- Spearmint 3
- American basil 3
- Avocado 3
- Vera cruz pepper 3
- Europe sage 3
- Winter savory 3
- Russian Potato 3
- Clove 3
- Feverfew 3
- T. longicaulis 3
- Chinese chastetree 3
- Corn 3
- A. pinsapo subsp. marocana 2
- Yarrow 2
- A. citriodora 2
- Lemon Verbena 2
- A. triphylla 2
- A. breviligulata 2
- A. latilabris 2
- Soursop 2
- A. birostris 2
- A. cymbifera 2
- A. gigantea 2
- A. macroura 2
- Wormwood 2
- A. afra 2
- A. arborescens 2
- Mugwort 2
- A. fauriei 2
- A. yakusimense 2
- B. articulata 2
- B. rufescens 2
- B. semistriata 2
- B. pubescens litwinowii 2
- Tea 2
- Hemp 2
- C. mutabilis 2
- Centella 2
- Sawara Cypress 2
- C. ambiguum 2
- Camphorwood 2
- Pink rock-rose 2
- C. grandis 2
- Kaffir Lime 2
- Shaddock 2
- Citron 2
- C. carolinianum 2
- C. grandiflorum 2
- Langsdorf's copaifera 2
- C. langsdorfii 2
- Coriander 2
- C. grewioides 2
- C. sonderianus 2
- C. zehntneri 2
- C. agathophylla 2
- Sugi 2
- Mango ginger 2
- Rosha grass 2
- E. tournefortii 2
- Crested latesummer mint 2
- E. canadensis 2
- Tumbledown gum 2
- Fig 2
- Fennel 2
- F. falciloba 2
- H. ambiguum 2
- H. dissectum 2
- H. inuloides 2
- Virginia heartleaf 2
- Chameleon 2
- Sweet-amber 2
- St John's wort 2
- Tropical bushmint 2
- Marubio 2
- Hyssop 2
- Staranise 2
- Persian Walnut 2
- Prickly Juniper 2
- L. alata 2
- Lantana 2
- L. ukambensis 2
- Siberian Larch 2
- Lavender 2
- Spike Lavendar 2
- Mānuka 2
- Summer ragwort 2
- Mexican oregano 2
- Japanese Big Leaf Magnolia 2
- Magnolia-bark 2
- Mango 2
- M. alternifolia 2
- Punktree 2
- Water Mint 2
- Horse Mint 2
- Apple Mint 2
- M. pyrifolia 2
- M. mollis 2
- N. fissa 2
- N. nuda 2
- N. viscida 2
- Least basil 2
- O. phlogopappa 2
- Dittany of Crete 2
- O. minutiflorum 2
- Pot marjoram 2
- P. ternifolium 2
- P. frutescens var. hirtella 2
- P. atriplicifolia 2
- Bosnian Pine 2
- Masson's Pine 2
- Scots Pine 2
- Higuillo de hoja menuda 2
- P. regnellii 2
- P. uloptera 2
- R. dauricum 2
- S. absconditiflora 2
- S. dorisiana 2
- Apple-bearing sage 2
- S. syriaca 2
- S. tomentosa 2
- S. lazica 2
- Peruvian peppertree 2
- S. amasiaca 2
- S. condensata 2
- S. lyciae 2
- Canada goldenrod 2
- Muster John Henry 2
- Taiwania 2
- T. annuum 2
- Tansy 2
- Mountain germander 2
- T. polium 2
- T. pseudoscorodonia 2
- T. sandrasicum 2
- T. carvifolius 2
- Thyme 2
- T. broussonetii 2
- T. kotschyanus 2
- T. maroccanus 2
- T. nummularius 2
- Large Thyme 2
- T. sibthorpii 2
- Baboonwood 2
- V. annua 2
- Rough cockleburr 2
- Cockle bur 2
- X. sericea 2
- Z. armatum 2
- Z. multiflora 2
- Silver Fir 1
- Cilician Fir 1
- Caucasian Fir 1
- Sakhalin Fir 1
- Siberian Fir 1
- Monkeybush 1
- Hispid starbur 1
- A. sellowiana 1
- A. abrotanoides 1
- Sweet-Nancy 1
- A. arabica 1
- A. asiatica 1
- A. biebersteinii 1
- A. collina 1
- Yarrow 1
- A. erba-rotta 1
- A. grandifolia 1
- A. moschata 1
- A. nana 1
- Noble yarrow 1
- Sneezewort 1
- A. africanum 1
- Sweetflag 1
- A. simplex 1
- A. acuminata 1
- A. longifolia 1
- Indian bael 1
- A. parvifolius 1
- Horse-chestnut 1
- A. mannii 1
- Blue giant hyssop 1
- A. rugosa 1
- A. anisochroma 1
- A. ligustrina 1
The 240 best-attested of 1,082 organisms, ranked by how many independent papers report the compound in each. Occurrence data from LOTUS, across 1,060 references.
Pharmacology
Protein interactions
-
Cannabinoid receptor 2 Ki 0.15 uM
-
Peroxisome proliferator-activated receptor alpha EC50 9.58 uM
Laboratory measurements of the compound at its own doses. They do not describe any product that contains it.
Reported associations
Disease associations
-
Contact dermatitis, allergic Skin Disease
Associations recorded for the compound itself. A metabolomics association means it was detected or studied in that condition, not that it treats or causes it; an occupational entry describes a hazard of exposure. Neither is a therapeutic claim about any product.
Human evidence in progress
Registered clinical trials
-
Analgesic and Subjective Effects of Terpenes active not recruiting
-
Beta Caryophyllene & Apnea Performance completed
-
Acute Changes In Thermal Pain Response Following Single Oral Dose of Beta-Cary withdrawn
5 registered on ClinicalTrials.gov naming this molecule as an intervention. See all terpene trials.
Evidence
Literature
-
Anticonvulsant activity of β-caryophyllene against pentylenetetrazol-induced seizures
-
Beta-caryophyllene enhances wound healing through multiple routes
-
Beta-caryophyllene in psychiatric and neurological diseases: Role of blood-brain barrier
-
Cannabidiol and Beta-Caryophyllene: Chronic inflammatory pain
-
β-caryophyllene and β-caryophyllene oxide-natural compounds of anticancer and analgesic properties