MOLECULE
Limonene
Limonene is a monoterpene that is cyclohex-1-ene substituted by a methyl group at position 1 and a prop-1-en-2-yl group at position 4 respectively. It has a role as a human metabolite. It is a cycloalkene and a p-menthadiene.
Summary from ChEBI, via PubChem.
Identity
Chemistry
- Formula
- C10H16
- Molecular weight
- 136.23 g/mol
- IUPAC name
- 1-methyl-4-prop-1-en-2-ylcyclohexene
- InChIKey
- XMGQYMWWDOXHJM-UHFFFAOYSA-N
- SMILES
- CC1=CCC(CC1)C(=C)C
- PubChem
- CID 22311 ↗
Provenance
Contributing sources
- PubChem
- ChEBI
- LOTUS
Natural occurrence
Found in
- Fennel 12
- Spearmint 8
- Sage 8
- Chaste-tree 8
- Dill 7
- L. multiflora 7
- M. alternifolia 7
- R. officinalis 7
- Citron 5
- Wild Carrot 5
- Oregano 5
- Greek oregano 5
- Muster John Henry 5
- Corn 5
- Greater galangal 4
- Shellplant 4
- Caraway 4
- Grapefruit 4
- Sea fennel 4
- Torch-ginger 4
- River redgum 4
- Tasmanian bluegum 4
- Human 4
- M. piperita 4
- Syrian oregano 4
- Persian zatar 4
- Peruvian peppertree 4
- Balsam Fir 3
- A. citriodora 3
- Lemon Verbena 3
- A. triphylla 3
- A. breviligulata 3
- A. chinensis 3
- Wild Celery 3
- Rape 3
- Jack in the bush 3
- C. grandis 3
- Shaddock 3
- C. carolinianum 3
- C. grandiflorum 3
- Lemonscented gum 3
- Common turmeric 3
- East Indian lemongrass 3
- E. canadensis 3
- American tarwort 3
- Siberian Larch 3
- Sweet Gum 3
- Myrtle 3
- Sweet basil 3
- African basil 3
- Korean perilla 3
- Europe sage 3
- Feverfew 3
- T. capitata 3
- T. spicata 3
- Thymus 3
- T. longicaulis 3
- Thyme 3
- Common Valerian 3
- Z. armatum 3
- Ginger 3
- Shampoo Ginger 3
- Silver Fir 2
- Grand Fir 2
- A. arabica 2
- A. biebersteinii 2
- Blue giant hyssop 2
- Tropical whiteweed 2
- A. arborescens 2
- A. fauriei 2
- A. fauriei var. takaoi 2
- A. paludosa 2
- B. articulata 2
- B. rufescens 2
- B. carteri 2
- Frankincense 2
- Caucasian bluestem 2
- B. campestris 2
- Black mustard 2
- Wild turnip 2
- Shrubby Hare's Ear 2
- B. canariensis 2
- B. mollis 2
- Lawson's Cypress 2
- Hinoki Cypress 2
- Sawara Cypress 2
- Roman Chamomile 2
- Mexican tea 2
- C. deliciosa 2
- Kaffir Lime 2
- Mandarin orange 2
- Browne's savory 2
- Coriander 2
- C. agathophylla 2
- Sugi 2
- Mango ginger 2
- Curcuma 2
- C. kwangsiensis 2
- C. phaeocaulis 2
- C. wenyujin 2
- C. xanthorrhiza 2
- Zedoary 2
- Lemon grass 2
- Rosha grass 2
- D. cachrydifolia 2
- Mexican tea 2
- E. chrysantha 2
- E. orientalis 2
- E. tenuifolia 2
- E. trichophylla 2
- H. odoratissimum 2
- H. dissectum 2
- Pignut 2
- Common Juniper 2
- L. cuminoides 2
- Dahurian Larch 2
- L. trilobum 2
- Garden lovage 2
- Porter lovage 2
- L. dulcis 2
- L. javanica 2
- Mango 2
- Cajeput tree 2
- Punktree 2
- Water Mint 2
- M. canadensis 2
- Apple Mint 2
- M. mollis 2
- N. glomerulosa 2
- N. viscida 2
- Dittany of Crete 2
- Pot marjoram 2
- Guayule 2
- P. lanata 2
- Norway Spruce 2
- P. abies var. abies 2
- P. pauciflorus 2
- Scots Pine 2
- Vera cruz pepper 2
- Black pepper 2
- Pistachio 2
- Hardy orange 2
- Yerba porosa 2
- P. uloptera 2
- S. dorisiana 2
- Apple-bearing sage 2
- S. syriaca 2
- S. tomentosa 2
- Lavender cotton 2
- Winter savory 2
- Coast Redwood 2
- S. amasiaca 2
- S. lyciae 2
- Canada goldenrod 2
- Bay Biscayne creeping-oxeye 2
- Mountain germander 2
- T. pestalozzae 2
- T. sandrasicum 2
- Northern Whitecedar 2
- Thyme 2
- T. saturejoides 2
- T. sibthorpii 2
- T. zygis 2
- Tree marigold 2
- V. ashei 2
- Highbush blueberry 2
- Swamp Blueberry 2
- Baboonwood 2
- Rough cockleburr 2
- Cockle bur 2
- X. sericea 2
- Z. chalybaeum 2
- Z. chalybeum 2
- Caucasian Fir 1
- Sakhalin Fir 1
- Siberian Fir 1
- A. asiatica 1
- A. collina 1
- A. cuneatiloba 1
- A. erba-rotta 1
- A. grandifolia 1
- Yarrow 1
- A. moschata 1
- A. nana 1
- Noble yarrow 1
- Sneezewort 1
- A. africanum 1
- A. japonica 1
- A. simplex 1
- A. cunninghamii 1
- Indian bael 1
- Horse-chestnut 1
- A. daniellii 1
- Melegueta pepper 1
- A. sulcatum 1
- A. mannii 1
- A. formosana 1
- A. rugosa 1
- Cape buchu 1
- A. fastigiata 1
- Ground-pine 1
- Whitebrush 1
- A. latilabris 1
- Amaryllids 1
- Roman wormwood 1
- A. beaumonti 1
- A. papuanus 1
- Laceflower 1
- A. coaetaneus 1
- A. maximus 1
- A. gigas 1
- A. puchury-minor 1
- A. cascarilloides 1
- Pond Apple 1
- Soursop 1
- Custard apple 1
- Umbellifers 1
- A. asclepiadifolia 1
- Birthwort family 1
- Chickensage 1
- Wormwood 1
- A. afra 1
- A. capillaris 1
- Tarragon 1
- A. halophila 1
- White wormwood 1
- A. jacutica 1
- A. judaica 1
- A. lagocephala 1
- A. macrocephala 1
- A. monosperma 1
- A. rubripes 1
- Saline Wormwood 1
- A. spicigera 1
- A. szowitziana 1
- A. thuscula 1
- Mugwort 1
- Snakeshead 1
- Canadian wildginger 1
- A. celsum 1
The 240 best-attested of 861 organisms, ranked by how many independent papers report the compound in each. Occurrence data from LOTUS, across 829 references.
Pharmacology
Protein interactions
-
AR protein Potency 28.2808 uM
-
nuclear factor erythroid 2-related factor 2 isoform 1 Potency 1122.02 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
-
Behavioral Pharmacology of Orally Administered THC and D-limonene recruiting
-
CYP2C19 Variants and Limonene Metabolism recruiting
-
d-Limonene +Radiation +PlatinumBasedChemo for Xerostomia Prevention in LocallyAdvanced HNSCC recruiting
-
New Non-invasive Biomarkers of Metabolic Dysfunction-associated Steatotic Liver Disease (MASLD) completed
-
Human Breast Tissue Bioavailability of Topically Applied Limonene completed
8 registered on ClinicalTrials.gov naming this molecule as an intervention. See all terpene trials.
Evidence