MOLECULE
α-Pinene
Alpha-pinene is a pinene that is bicyclo[3.1.1]hept-2-ene substituted by methyl groups at positions 2, 6 and 6 respectively. It has a role as a plant metabolite.
Summary from ChEBI, via PubChem.
Identity
Chemistry
- Formula
- C10H16
- Molecular weight
- 136.23 g/mol
- IUPAC name
- 2,6,6-trimethylbicyclo[3.1.1]hept-2-ene
- InChIKey
- GRWFGVWFFZKLTI-UHFFFAOYSA-N
- SMILES
- CC1=CCC2CC1C2(C)C
- PubChem
- CID 6654 ↗
Provenance
Contributing sources
- PubChem
- ChEBI
- LOTUS
Natural occurrence
Found in
- Sage 14
- M. alternifolia 12
- Fennel 11
- R. officinalis 11
- Sweet wormwood 8
- Chaste-tree 8
- Wild Carrot 7
- Persian zatar 7
- Greater galangal 6
- Dill 6
- Pignut 6
- Ginger 6
- Roman Chamomile 5
- Citron 5
- Common turmeric 5
- Tasmanian bluegum 5
- Spearmint 5
- Oregano 5
- Scots Pine 5
- Greek oregano 5
- T. capitata 5
- Thymus 5
- Corn 5
- Shellplant 4
- C. deliciosa 4
- C. grandis 4
- Shaddock 4
- Mandarin orange 4
- Torch-ginger 4
- Heterotropa 4
- L. multiflora 4
- Myrtle 4
- Syrian oregano 4
- T. quinquecostatus 4
- Thyme 4
- Common Valerian 4
- W. villosa 4
- Cassumunar ginger 4
- Shampoo Ginger 4
- Tropical whiteweed 3
- A. citriodora 3
- Lemon Verbena 3
- A. triphylla 3
- A. breviligulata 3
- A. chinensis 3
- Round cardamom 3
- A. krervanh 3
- Wormwood 3
- Big sagebrush 3
- Rape 3
- Jack in the bush 3
- C. carolinianum 3
- C. grandiflorum 3
- Coriander 3
- Lemonscented gum 3
- C. grewioides 3
- C. nepetifolius 3
- C. zehntneri 3
- Mediterranean Cypress 3
- East Indian lemongrass 3
- River redgum 3
- H. odoratissimum 3
- Common Juniper 3
- Siberian Larch 3
- Sweet Gum 3
- Sweet basil 3
- African basil 3
- Norway Spruce 3
- Ponderosa Pine 3
- Sage 3
- S. absconditiflora 3
- S. hydrangea 3
- Lavender cotton 3
- Winter savory 3
- Coast Redwood 3
- Muster John Henry 3
- Feverfew 3
- Tansy 3
- T. spicata 3
- T. eriocalyx 3
- T. kotschyanus 3
- T. longicaulis 3
- W. compacta 3
- W. longiligularis 3
- X. sericea 3
- A. arabica 2
- A. biebersteinii 2
- A. conchigera 2
- A. latilabris 2
- Wild Celery 2
- Birthwort family 2
- Chickensage 2
- Tarragon 2
- White wormwood 2
- Mugwort 2
- A. asperum 2
- A. fauriei 2
- A. fauriei var. takaoi 2
- A. hypogynum 2
- A. megacalyx 2
- A. paludosa 2
- B. articulata 2
- B. rufescens 2
- B. carteri 2
- Frankincense 2
- Caucasian bluestem 2
- Shrubby Hare's Ear 2
- C. mutabilis 2
- Taiwan Cypress 2
- Lawson's Cypress 2
- Hinoki Cypress 2
- Sawara Cypress 2
- Padang cassia 2
- Cinnamon 2
- Kaffir Lime 2
- C. unshiu 2
- C. patens 2
- Browne's savory 2
- Sea fennel 2
- C. sonderianus 2
- C. agathophylla 2
- Sugi 2
- C. pierreana 2
- Rosha grass 2
- E. chrysantha 2
- E. orientalis 2
- E. tenuifolia 2
- E. tournefortii 2
- Crested latesummer mint 2
- E. canadensis 2
- Fitweed 2
- Sugargum 2
- Tumbledown gum 2
- Karri 2
- E. maidenii 2
- Gray ironbark 2
- Gray gum 2
- Forest redgum 2
- Asafoetida 2
- Crane's-bills 2
- Matchbrush 2
- H. dissectum 2
- Littlebrownjug 2
- Virginia heartleaf 2
- Houttuynia 2
- Sweet-amber 2
- H. perfoliatum 2
- St John's wort 2
- Tropical bushmint 2
- Hyssop 2
- Black Walnut 2
- L. cuminoides 2
- Dahurian Larch 2
- L. trilobum 2
- Spike Lavendar 2
- French lavender 2
- Garden lovage 2
- Scots Lovage 2
- L. dulcis 2
- L. origanoides 2
- Weeping Paperbark 2
- Cajeput tree 2
- Punktree 2
- Water Mint 2
- M. mollis 2
- Chinese box 2
- Orange jasmine 2
- N. glomerulosa 2
- N. viscida 2
- Black cumin 2
- Least basil 2
- O. phlogopappa 2
- Dittany of Crete 2
- O. minutiflorum 2
- Pot marjoram 2
- Guayule 2
- Avocado 2
- Parsley 2
- P. lanata 2
- Bayrumtree 2
- Afghan pine 2
- Japanese Red Pine 2
- Masson's Pine 2
- Dwarf Stone Pine 2
- Vera cruz pepper 2
- Marigold pepper 2
- Pistachio 2
- Hardy orange 2
- P. uloptera 2
- Guava 2
- S. viticulosa 2
- S. dorisiana 2
- S. dorystaechas 2
- Apple-bearing sage 2
- Europe sage 2
- S. syriaca 2
- S. tomentosa 2
- Summer savory 2
- S. amasiaca 2
- S. congesta 2
- S. lyciae 2
- Canada goldenrod 2
- Bay Biscayne creeping-oxeye 2
- Mountain germander 2
- T. sandrasicum 2
- Northern Whitecedar 2
- Thyme 2
- T. broussonetii 2
- Cilician thyme 2
- T. nummularius 2
- T. piperella 2
- T. revolutus 2
- T. saturejoides 2
- T. sibthorpii 2
- T. zygioides 2
- T. zygis 2
- Tree marigold 2
- California laurel 2
- V. persicifolia 2
- Baboonwood 2
- Chinese chastetree 2
- Ethiopian pepper 2
- Z. gilletii 2
- Balsam Fir 1
- Cilician Fir 1
- Caucasian Fir 1
- Sakhalin Fir 1
- Siberian Fir 1
- A. nuperrima 1
- A. abrotanoides 1
- A. asiatica 1
- A. collina 1
- Yarrow 1
- A. cuneatiloba 1
- A. erba-rotta 1
- A. grandifolia 1
- Yarrow 1
- A. moschata 1
- A. nana 1
- Noble yarrow 1
The 240 best-attested of 1,019 organisms, ranked by how many independent papers report the compound in each. Occurrence data from LOTUS, across 974 references.
Pharmacology
Protein interactions
-
Cytochrome P450 1A2 Potency 3.5481 uM
-
cytochrome P450 2D6 Potency 7.098 uM
Laboratory measurements of the compound at its own doses. They do not describe any product that contains it.
Reported associations
Disease associations
-
Solvents, acute toxic effect Acute Poisoning
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
Literature
-
Efficient Biosynthesis of (+)-α-Pinene and de Novo Synthesis of (+)-cis-Verbenol in Escherichia coli
-
Extraction and purification of α-pinene; a comprehensive review
-
The effects of alpha-pinene on inflammatory responses and oxidative stress in the formalin test
-
The effects of alpha-pinene on the Nrf2-HO1 signaling pathway in gastric damage in rats