MOLECULE
Caryophyllene oxide
Caryophyllene oxide is an epoxide. It has a role as a metabolite.
Summary from ChEBI, via PubChem.
Identity
Chemistry
- Formula
- C15H24O
- Molecular weight
- 220.35 g/mol
- IUPAC name
- (1R,4R,6R,10S)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.04,6]dodecane
- InChIKey
- NVEQFIOZRFFVFW-RGCMKSIDSA-N
- SMILES
- CC1(CC2C1CCC3(C(O3)CCC2=C)C)C
- PubChem
- CID 1742210 ↗
Provenance
Contributing sources
- PubChem
- ChEBI
- LOTUS
Natural occurrence
Found in
- Korean perilla 8
- Hops 7
- Wild cinnamon 5
- Chaste-tree 5
- Sweet basil 4
- Common Valerian 4
- Tropical whiteweed 3
- A. breviligulata 3
- A. chinensis 3
- Shellplant 3
- Wild Celery 3
- Mugwort 3
- Torch-ginger 3
- Chameleon 3
- Spike Lavendar 3
- L. multiflora 3
- Holy basil 3
- Oregano 3
- Black pepper 3
- Guava 3
- R. officinalis 3
- Greek oregano 3
- Sage 3
- T. capitata 3
- Thymus 3
- Sweetflag 2
- A. leucophylla 2
- A. citriodora 2
- Lemon Verbena 2
- A. triphylla 2
- Greater galangal 2
- Climbing ilang-ilang 2
- Wormwood 2
- Sweet wormwood 2
- A. lagocephala 2
- B. dracunculifolia 2
- B. palmensis 2
- B. pendula 2
- Caucasian bluestem 2
- Peacock Flower 2
- Hemp 2
- C. recutita 2
- C. ambiguum 2
- Cinnamon 2
- C. zeylanicum 2
- C. deliciosa 2
- Mandarin orange 2
- C. patens 2
- C. carolinianum 2
- C. grandiflorum 2
- Mango ginger 2
- Rosha grass 2
- Nut-grass 2
- G. scorzonerifolia 2
- H. ambiguum 2
- Pignut 2
- Common Juniper 2
- Mango 2
- Wild Chamomile 2
- Balm 2
- Water Mint 2
- Myrtle 2
- N. nuda 2
- Vera cruz pepper 2
- S. hydrangea 2
- S. palaefolia 2
- Europe sage 2
- S. lyciae 2
- S. sumatrana 2
- Clove 2
- Northern Whitecedar 2
- T. longicaulis 2
- Thyme 2
- V. fauriei 2
- Shampoo Ginger 2
- Cilician Fir 1
- Monkeybush 1
- Rayless goldenhead 1
- A. coarctata 1
- A. erba-rotta 1
- Yarrow 1
- A. moschata 1
- A. nana 1
- Noble yarrow 1
- Sneezewort 1
- A. africanum 1
- Indian bael 1
- Longoza Plant 1
- A. cereum 1
- Melegueta pepper 1
- A. sceptrum 1
- Blue giant hyssop 1
- A. rugosa 1
- A. ligustrina 1
- A. foveolata 1
- Whitebrush 1
- A. latilabris 1
- Sea torchwood 1
- Sugar apple 1
- A. aciphylla 1
- A. laciniatum 1
- A. denticulatus 1
- A. birostris 1
- A. lastoursvillensis 1
- A. stenopetalus 1
- A. arborescens 1
- A. rubripes 1
- A. santolinifolia 1
- A. stechmanniana 1
- A. thuscula 1
- A. scaber 1
- A. vayredana 1
- Austrobaileya 1
- A. patens 1
- A. inulifolium 1
- A. dulcis 1
- A. tenuifolia 1
- B. articulata 1
- Bigelow's false willow 1
- B. coridifolia 1
- Groundsel Bush 1
- B. heterophylla 1
- Yerba de pasmo 1
- B. rufescens 1
- Emory baccharis 1
- Desertbroom 1
- B. erythrophloia 1
- Asian White Birch 1
- B. pubescens litwinowii 1
- Shoofly 1
- B. graveolens 1
- B. zanguebaricum 1
- B. salicifolius 1
- B. tweediei 1
- B. albiflora 1
- B. carteri 1
- Elemi frankincense 1
- Frankincense 1
- B. neurococca 1
- California brickellbush 1
- Splitleaf brickellbush 1
- Ox-eye 1
- B. acutifolium 1
- B. canariensis 1
- B. mollis 1
- C. incana 1
- C. jamaicensis 1
- C. pilosa 1
- C. prunifolia 1
- C. warszewiczianus 1
- Tea 1
- C. mutabilis 1
- C. parviflorum 1
- C. ipecacuanha 1
- C. aegyptiaca 1
- Centella 1
- Taiwan Cypress 1
- C. lopadusanus 1
- C. connivens 1
- C. laevigata 1
- Jack in the bush 1
- Selasian Wood 1
- C. sieboldii 1
- C. subavenium 1
- Pink rock-rose 1
- Citron 1
- C. excavata 1
- C. lusitanica 1
- C. album 1
- Ashe's calamint 1
- C. barbatum 1
- C. brevifolium 1
- Browne's savory 1
- C. insulare 1
- C. thymifolium 1
- Asthmaweed 1
- C. sumatrensis 1
- C. guianensis 1
- Langsdorf's copaifera 1
- C. langsdorfii 1
- Copaifera 1
- Lemonscented gum 1
- C. cochinchinense 1
- Cortez's croton 1
- Cascarilla 1
- C. nepetifolius 1
- Yerba 1
- C. agathophylla 1
- C. plicatum 1
- C. fasciculata 1
- C. microcephala 1
- C. cinerea 1
- Mediterranean Cypress 1
- Curcuma 1
- Common turmeric 1
- C. pierreana 1
- C. trichosantha 1
- C. purpurea 1
- East Indian lemongrass 1
- C. khasianus 1
- C. erectus 1
- Red Pine 1
- D. nausoriense 1
- Wild Carrot 1
- D. trifidus 1
- D. confinis 1
- D. hirsuta 1
- E. tournefortii 1
- Crested latesummer mint 1
- E. eriostachya 1
- E. manipuliflora 1
- E. bonariensis 1
- Fitweed 1
- E. stephanii 1
- E. angulosa 1
- Bull mallee 1
- River redgum 1
- E. ceratocorys 1
- Mallee Box 1
- Tumbledown gum 1
- E. dolichorhyncha 1
- E. fasciculosa 1
- Fuschia gum 1
- Tasmanian bluegum 1
- Lerp Mallee 1
- E. intertexta 1
- E. lansdowneana 1
- White ironbark 1
- E. maidenii 1
- Silver-leaf ironbark 1
- E. ochrophloia 1
- E. odorata 1
- E. populnea 1
- E. porosa 1
- E. sparsa 1
- Scarlett Pear Gum 1
- E. tetraptera 1
- Green Mallee 1
- Tall thoroughwort 1
- F. pratensis 1
The 240 best-attested of 490 organisms, ranked by how many independent papers report the compound in each. Occurrence data from LOTUS, across 480 references.
Pharmacology
Protein interactions
-
Ferritin heavy chain IC50 0.001 uM
Laboratory measurements of the compound at its own doses. They do not describe any product that contains it.
Evidence
Literature
-
Stimulation of Hemolysis and Eryptosis by β-Caryophyllene Oxide
-
Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects
-
β-caryophyllene and β-caryophyllene oxide-natural compounds of anticancer and analgesic properties
-
β-caryophyllene oxide induces apoptosis and inhibits proliferation of A549 lung cancer cells