MOLECULE
Terpinolene
Terpinolene is a p-menthadiene with double bonds at positions 1 and 4(8). It has a role as a volatile oil component, a sedative, an insect repellent and a plant metabolite.
Summary from ChEBI, via PubChem.
Identity
Chemistry
- Formula
- C10H16
- Molecular weight
- 136.23 g/mol
- IUPAC name
- 1-methyl-4-propan-2-ylidenecyclohexene
- InChIKey
- MOYAFQVGZZPNRA-UHFFFAOYSA-N
- SMILES
- CC1=CCC(=C(C)C)CC1
- PubChem
- CID 11463 ↗
Provenance
Contributing sources
- PubChem
- ChEBI
- LOTUS
Natural occurrence
Found in
- M. alternifolia 15
- Shellplant 5
- Wild Carrot 5
- Torch-ginger 5
- C. deliciosa 4
- Mandarin orange 4
- Siberian Larch 4
- M. piperita 4
- Myrtle 4
- Black pepper 4
- R. officinalis 4
- Common Valerian 4
- Ginger 4
- Camphorwood 3
- C. grandis 3
- Shaddock 3
- Citron 3
- Coriander 3
- Pignut 3
- Common Juniper 3
- Sweet Gum 3
- African basil 3
- Syrian oregano 3
- Oregano 3
- Korean perilla 3
- Norway Spruce 3
- Scots Pine 3
- Guava 3
- Greek oregano 3
- Sage 3
- Lavender cotton 3
- Coast Redwood 3
- Tansy 3
- Northern Whitecedar 3
- T. longicaulis 3
- Thyme 3
- Chaste-tree 3
- Tropical whiteweed 2
- A. citriodora 2
- Lemon Verbena 2
- A. triphylla 2
- Greater galangal 2
- A. arborescens 2
- B. articulata 2
- B. rufescens 2
- Khat 2
- Lawson's Cypress 2
- Sawara Cypress 2
- Pink rock-rose 2
- Kaffir Lime 2
- Grapefruit 2
- C. unshiu 2
- C. agathophylla 2
- Sugi 2
- C. xanthorrhiza 2
- E. chrysantha 2
- E. tenuifolia 2
- E. canadensis 2
- H. odoratissimum 2
- Syrian Juniper 2
- Dahurian Larch 2
- L. dulcis 2
- Mango 2
- Cajeput tree 2
- Orange jasmine 2
- N. viscida 2
- American basil 2
- Sweet basil 2
- Guayule 2
- Bayrumtree 2
- Aleppo Pine 2
- Ponderosa Pine 2
- Vera cruz pepper 2
- S. absconditiflora 2
- S. dorisiana 2
- S. dorystaechas 2
- S. syriaca 2
- S. tomentosa 2
- S. lyciae 2
- T. broussonetii 2
- T. sibthorpii 2
- T. zygioides 2
- T. zygis 2
- California laurel 2
- Z. chalybaeum 2
- Z. chalybeum 2
- Balsam Fir 1
- Sakhalin Fir 1
- Siberian Fir 1
- A. abrotanoides 1
- A. arabica 1
- A. biebersteinii 1
- Yarrow 1
- Sweetflag 1
- A. cunninghamii 1
- Buchu 1
- Cape buchu 1
- Cultivated garlic 1
- Whitebrush 1
- A. conchigera 1
- A. latilabris 1
- A. beaumonti 1
- A. papuanus 1
- Dill 1
- Norwegian angelica 1
- A. antipoda 1
- A. cascarilloides 1
- Sugar apple 1
- A. aciphylla 1
- Wild Celery 1
- Hoop Pine 1
- Wormwood 1
- A. afra 1
- Sweet wormwood 1
- White wormwood 1
- A. lagocephala 1
- A. rubripes 1
- A. spicigera 1
- A. thuscula 1
- Snakeshead 1
- Canadian wildginger 1
- A. scaber 1
- A. macedonica 1
- Austrobaileya 1
- Neem Tree 1
- B. dracunculifolia 1
- Baeckea 1
- B. bassiana 1
- B. sulfurescens 1
- Daisy 1
- B. salicifolius 1
- B. tweediei 1
- B. latipinna 1
- B. carteri 1
- Frankincense 1
- Shrubby Hare's Ear 1
- B. canariensis 1
- B. mollis 1
- Pink Node Flower 1
- C. incana 1
- Narrow-leaf bottlebrush 1
- C. nootkatensis 1
- Tea 1
- Elemi tree 1
- Wild cinnamon 1
- Hemp 1
- C. mutabilis 1
- Papaya 1
- Lebanon Cedar 1
- C. azoricum 1
- Hinoki Cypress 1
- Jack in the bush 1
- Florist's daisy 1
- C. sieboldii 1
- Cinnamon 1
- C. zeylanicum 1
- C. albidus 1
- Labdanum 1
- C. laurifolius 1
- Montpelier cistus 1
- C. wilsonii 1
- C. excavata 1
- C. patens 1
- C. lusitanica 1
- C. album 1
- C. barbatum 1
- C. brevifolium 1
- C. carolinianum 1
- C. congestum 1
- C. grandiflorum 1
- C. insulare 1
- C. thymifolium 1
- C. timotensis 1
- Asthmaweed 1
- C. incana 1
- Asiatic dogwood 1
- Lemonscented gum 1
- European smoketree 1
- Cannonball Tree 1
- Sea fennel 1
- Cascarilla 1
- C. jacobinensis 1
- C. nepetifolius 1
- C. sonderianus 1
- C. stellulifer 1
- C. stelluliferus 1
- Cumin 1
- Monterey cypress 1
- Mediterranean Cypress 1
- Curcuma 1
- Common turmeric 1
- C. pierreana 1
- C. niveum 1
- Lemon grass 1
- East Indian lemongrass 1
- Rosha grass 1
- Sedges 1
- Nut-grass 1
- D. nausoriense 1
- D. nidulum 1
- E. fruticosa 1
- E. pilosa 1
- E. bonariensis 1
- E. timotensis 1
- Waxflower 1
- E. pavieana 1
- E. angulosa 1
- Whitebark 1
- E. approximans 1
- Bull mallee 1
- E. brassiana 1
- Applebox 1
- River redgum 1
- E. ceratocorys 1
- Cloeziana gum 1
- E. crenulata 1
- Mallee Box 1
- Alpine-ash 1
- E. dendromorpha 1
- E. dolichorhyncha 1
- E. fasciculosa 1
- Fuschia gum 1
- Tasmanian bluegum 1
- Flooded Gum 1
- Lerp Mallee 1
- E. intertexta 1
- Wandi Ironbark 1
- E. lansdowneana 1
- White ironbark 1
- E. maidenii 1
- Silver-leaf ironbark 1
- Shining gum 1
- E. ochrophloia 1
- E. odorata 1
- E. paliformis 1
- E. populnea 1
- E. porosa 1
- Silver-leaved Mountain Gum 1
- Narrow-leaf peppermint gum 1
- E. sparsa 1
The 240 best-attested of 521 organisms, ranked by how many independent papers report the compound in each. Occurrence data from LOTUS, across 505 references.
Pharmacology
Protein interactions
-
cytochrome P450 family 3 subfamily A polypeptide 4 Potency 20.0048 uM
-
Cytochrome P450 3A4 Potency 39.8107 uM
-
cytochrome P450 family 2 subfamily C polypeptide 9 Potency 39.9149 uM
-
pregnane X nuclear receptor Potency 43.2771 uM
-
estrogen nuclear receptor alpha Potency 68.5896 uM
-
cytochrome P450, family 2, subfamily C, polypeptide 19 Potency 79.6407 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
1 registered on ClinicalTrials.gov naming this molecule as an intervention. See all terpene trials.
Evidence