1.0 2010-04-08 22:10:47 UTC 2025-11-18 23:47:13 UTC FDB013567 Limonene Found in over 300 essential oils, the ==(R)==-form is the most widespread, followed by the racemate and then the (S)-form. Extensively used in the flavour industry [DFC] 1-Methyl-4-(1-methylethenyl)cyclohexene, 9CI 1,8-p-menthadiene 4-isopropenyl-1-methylcyclohexene Cajeputene Carvene Citrene Cynene Diisoprene FEMA 2633 Hesperidene Isoterebentine Kautschine p-Mentha-1,8-diene Terpilene C10H16 136.238 136.125200515 1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene limonene, (+)- 138-86-3 CC(=C)C1CCC(C)=CC1 InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3 XMGQYMWWDOXHJM-UHFFFAOYSA-N belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Menthane monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cycloalkenes Monocyclic monoterpenoids Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Cycloalkene Hydrocarbon Monocyclic monoterpenoid Olefin P-menthane monoterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Menthane monoterpenoids Terpenoids a limonene monoterpene liquid logp 4.50 ALOGPS logs -2.47 ALOGPS solubility 4.57e-01 g/l ALOGPS melting_point -95 oC logp 3.22 ChemAxon iupac 1-methyl-4-(prop-1-en-2-yl)cyclohex-1-ene ChemAxon average_mass 136.238 ChemAxon mono_mass 136.125200515 ChemAxon smiles CC(=C)C1CCC(C)=CC1 ChemAxon formula C10H16 ChemAxon inchi InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3 ChemAxon inchikey XMGQYMWWDOXHJM-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 46.48 ChemAxon polarizability 17.55 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::EiMs 1903 Specdb::CMs 918 Specdb::CMs 5773 Specdb::CMs 27230 Specdb::CMs 154389 Specdb::MsMs 76188 Specdb::MsMs 76189 Specdb::MsMs 76190 Specdb::MsMs 135963 Specdb::MsMs 135964 Specdb::MsMs 135965 Specdb::MsMs 2227987 Specdb::MsMs 3060091 Specdb::MsMs 3060092 Specdb::MsMs 3060093 Specdb::MsMs 3109701 Specdb::MsMs 3109702 Specdb::MsMs 3109703 HMDB0032473 15384 Allspice Type 1 specific Pimenta dioica 375272 1.5 1.5 1.5 mg/100 g Anise Type 1 specific Pimpinella anisum 271192 213.25 213.25 213.25 mg/100 g Apple Type 1 specific Malus pumila 283210 Apricot Type 1 specific Prunus armeniaca 36596 Bilberry Type 1 specific Vaccinium myrtillus 180763 Black elderberry Type 1 specific Sambucus nigra 4202 Black tea Type 1 Black walnut Type 1 specific Juglans nigra 16719 1500.0 1500.0 1500.0 mg/100 g Blackberry Type 1 specific Rubus Blackcurrant Type 1 specific Ribes nigrum 78511 0.7 0.7 0.7 mg/100 g Broccoli Type 1 specific Brassica oleracea var. italica 36774 Caraway Type 1 specific Carum carvi 48032 972.0 1902.0 42.0 mg/100 g Cardamom Type 1 specific Elettaria cardamomum 105181 503.8 503.8 503.8 mg/100 g Carrot Type 1 specific Daucus carota ssp. sativus 79200 31.2 76.0 2.6 mg/100 g Cashew nut Type 1 specific Anacardium occidentale 171929 Cauliflower Type 1 specific Brassica oleracea var. botrytis 3715 Celeriac Type 1 specific Apium graveolens var. rapaceum 278110 Celery stalks Type 1 specific Apium graveolens var. dulce 117781 Ceylon cinnamon Type 1 specific Cinnamomum verum 128608 11.5 11.5 11.5 mg/100 g Chinese cinnamon Type 1 specific Cinnamomum aromaticum 119260 Coconut Type 1 specific Cocos nucifera 13894 Common grape Type 1 specific Vitis vinifera 29760 Common oregano Type 1 specific Origanum vulgare 39352 24.25 24.25 24.25 mg/100 g Common sage Type 1 specific Salvia officinalis 38868 120.95 120.95 120.95 mg/100 g Common thyme Type 1 specific Thymus vulgaris 49992 260.75 260.75 260.75 mg/100 g Coriander Type 1 specific Coriandrum sativum 4047 63.6 63.6 63.6 mg/100 g Corn Type 1 specific Zea mays 4577 116.666667 700.0 0.0 mg/100 g Cornmint Type 1 specific Mentha arvensis 292239 177.0 177.0 177.0 mg/100 g Cumin Type 1 specific Cuminum cyminum 52462 37.8 37.8 37.8 mg/100 g Dill Type 1 specific Anethum graveolens 40922 Evergreen blackberry Type 1 specific Rubus laciniatus Fennel Type 1 specific Foeniculum vulgare 48038 330.5 481.0 180.0 mg/100 g Fig Type 1 specific Ficus carica 3494 Fruit juice Type 2 specific Ginger Type 1 specific Zingiber officinale 94328 53.35 53.35 53.35 mg/100 g Grape Type 1 specific Vitis 3603 Grape wine Type 2 specific Green bean Type 1 specific Phaseolus vulgaris 3885 Green bell pepper Type 1 specific Capsicum annuum 4072 Green tea Type 1 Guava Type 1 specific Psidium guajava 120290 Herbal tea Type 1 Highbush blueberry Type 1 specific Vaccinium corymbosum 69266 Horseradish Type 1 specific Armoracia rusticana 3704 Hyssop Type 1 specific Hyssopus officinalis 39324 7.8 12.65 2.95 mg/100 g Lemon Type 1 specific Citrus limon 2708 539.8 539.8 539.8 mg/100 g Lemon balm Type 1 specific Melissa officinalis 39338 0.01 0.01 0.01 mg/100 g Lemon grass Type 1 specific Cymbopogon citratus 66014 Lime Type 1 specific Citrus aurantiifolia 159033 610.0 610.0 610.0 mg/100 g Linden Type 1 specific Tilia 64580 Lovage Type 1 specific Levisticum officinale 48042 4.4 4.4 4.4 mg/100 g Lowbush blueberry Type 1 specific Vaccinium angustifolium 472369 Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 795.0 795.0 795.0 mg/100 g Mango Type 1 specific Mangifera indica 29780 Mentha Type 1 specific Mentha 21819 Nutmeg Type 1 specific Myristica fragrans 51089 324.0 324.0 324.0 mg/100 g Oat Type 1 specific Avena sativa 4498 Orange bell pepper Type 1 specific Capsicum annuum 4072 Orange mint Type 1 specific Mentha aquatica 190902 23.1 41.4 4.8 mg/100 g Parsley Type 1 specific Petroselinum crispum 4043 37.7 73.8 1.6 mg/100 g Parsnip Type 1 specific Pastinaca sativa 4041 Pepper Type 1 specific Capsicum annuum 4072 Pepper (C. frutescens) Type 1 specific Capsicum annuum var. annuum 40321 Pepper (Spice) Type 1 specific Piper nigrum 13216 Peppermint Type 1 specific Mentha X piperita 34256 16.1 16.1 16.1 mg/100 g Pot marjoram Type 1 specific Origanum onites 452416 7.975 14.25 1.7 mg/100 g Prickly pear Type 1 specific Opuntia 106975 Pummelo Type 1 specific Citrus maxima 37334 Rabbiteye blueberry Type 1 specific Vaccinium virgatum Red bell pepper Type 1 specific Capsicum annuum 4072 Red tea Type 1 Red wine Type 2 9.1091 18.2 0.0182 mg/100 g Rocket salad (ssp.) Type 1 specific Eruca vesicaria ssp. sativa 29727 Roman camomile Type 1 specific Chamaemelum nobile 99037 Roselle Type 1 specific Hibiscus sabdariffa 183260 Rosemary Type 1 specific Rosmarinus officinalis 39367 45.916667 97.5 5.0 mg/100 g Safflower Type 1 specific Carthamus tinctorius 4222 0.001 0.001 0.001 mg/100 g Saffron Type 1 specific Crocus sativus 82528 Spearmint Type 1 specific Mentha spicata 29719 303.225 454.1 152.35 mg/100 g Star anise Type 1 specific Illicium verum 124778 266.0 266.0 266.0 mg/100 g Sugar apple Type 1 specific Annona squamosa 301693 Summer savory Type 1 specific Satureja hortensis 49987 Sunflower Type 1 specific Helianthus annuus 4232 Sweet basil Type 1 specific Ocimum basilicum 39350 46.8 46.8 46.8 mg/100 g Sweet bay Type 1 specific Laurus nobilis 85223 29.0 29.0 29.0 mg/100 g Sweet cherry Type 1 specific Prunus avium 42229 Sweet marjoram Type 1 specific Origanum majorana 268884 6.05 6.05 6.05 mg/100 g Sweet orange Type 1 specific Citrus sinensis 2711 456.975 900.0 13.95 mg/100 g Taco Type 2 specific 0.0 0.0 0.0 mg/100 g Tamarind Type 1 specific Tamarindus indica 58860 Tarragon Type 1 specific Artemisia dracunculus 72341 Tea Type 1 specific Camellia sinensis 4442 Tortilla Type 2 specific 0.0 0.0 0.0 mg/100 g Tortilla chip Type 2 specific Turmeric Type 1 specific Curcuma longa 136217 83.5 230.0 8.0 mg/100 g Wild carrot Type 1 specific Daucus carota 4039 31.2 76.0 2.6 mg/100 g Wild celery Type 1 specific Apium graveolens 4045 Winter savory Type 1 specific Satureja montana 49988 4.45 4.45 4.45 mg/100 g Yellow bell pepper Type 1 specific Capsicum annuum 4072 lemon orange Acaricide 16 A substance used to destroy pests of the subclass Acari (mites and ticks). Acetylcholinesterase inhibitor 21 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid. Allelochemic 41 Allergenic 43 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy. Anti acetylcholinesterase 76 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid. Anti adenomic 86 A substance that inhibits or prevents the proliferation of neoplasms. Anti bacterial 145 A substance that kills or slows the growth of bacteria. Anti esophagitic 271 Anti feedant 275 Anti metastatic 434 A substance that inhibits or prevents the proliferation of neoplasms. Anti septic 603 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-Alzheimeran 105 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-asthmatic 134 A drug used to treat asthma. Anti-cancer 159 A substance that inhibits or prevents the proliferation of neoplasms. Anti-flu 284 A substance that destroys or inhibits replication of viruses. Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-lithic 409 Anti-lymphomic 414 Anti-mutagenic 451 Anti-obesity 486 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-spasmodic 619 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-viral 689 A substance that destroys or inhibits replication of viruses. Antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. Apoptotic 704 Bronchoprotectant 739 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Cancer preventive 754 A substance that inhibits or prevents the proliferation of neoplasms. Candidistat 757 Chemopreventive 796 A substance that inhibits or prevents the proliferation of neoplasms. Cholesterolytic 802 Cytochrome-p450 inducer 854 Detoxicant 877 Any protective agent counteracting or neutralizing the action of poisons. Enterocontractant 906 Expectorant 925 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Fungiphilic 941 Fungistat 942 Glutathione-S-transferase inducer 964 Herbicide 986 A substance used to destroy plant pests. Histaminic 992 Immunomodulator 1031 Biologically active substance whose activity affects or plays a role in the functioning of the immune system. Insecticide 1040 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. Insectifuge 1041 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects. Interleukin-6 inhibitor 1051 A substance that diminishes the rate of a chemical reaction. Irritant 1055 Lipolytic 1074 Myorelaxant 1134 Name 936 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. Nematicide 1141 A substance used to destroy pests of the phylum Nematoda (roundworms). Nitric-oxide-genic 1166 Ornithine-decarboxylase inhibitor 1175 A compound or agent that combines with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. Ozone scavenger 1187 Peristaltic 1207 Pesticide 1210 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests. Photosensitizer 1221 Sedative 1311 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. Transdermal 1374