1.0 2010-04-08 22:11:22 UTC 2019-11-26 03:10:28 UTC FDB014616 1,8-Cineole Occurs in eucalyptus, lavender, sage and many other oils. Flavouring ingredient Eucalyptol is a natural organic compound which is a colorless liquid. It is a cyclic ether and a monoterpenoid.; Eucalyptol is an organic compound which is a colorless liquid. It is a cyclic ether and a monoterpene.; Eucalyptol is a natural constituent of a number of aromatic plants and their essential oil fraction. Eucalyptol was given GRAS (Generally Recognized As Safe) status by the Flavor and Extract Manufacturer's Association FEMA, 1965 and is approved by the Food and Drug Administration for food use. 1,8-Dihydroxy-10-carboxy-p-menthane, 2-hydroxy-cineole and 3-hydroxy-cineole are the main metabolites of Eucalyptol. Toxicological data available on eucalyptol are rather limited. Following the accidental exposure of human beings, death was reported in two cases after ingestion of 3.5-5 ml of essential eucalyptus oil, but a number of recoveries have also been described for much higher amounts of oil. In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes. It is added to improve the flavor. (PMID: 12048025, Fitoterapia. 2002 Jun;73(3):269-75); In a 1994 report released by five top cigarette companies, eucalyptol was listed as one of the 599 additives to cigarettes. It is claimed that it is added to improve the flavor.; It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. 1,8-Cineole is found in many foods, some of which are common thyme, caraway, sunflower, and pot marjoram. 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane 1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octane, 9CI 1,8-Cineol 1,8-Epoxy-P-menthane 1,8-Oxido-p-menthane 2-Oxa-1,3,3-trimethylbicyclo[2.2.2]octane 4,7,7-trimethyl-8-oxabicyclo[2.2.2]octane Cajeputol Cineol Cineole CNL Cucalyptol Cyneol Eucalyptol Eucalyptole Eucapur Eukalyptol FEMA 3658 Soledum Terpan Terpane Zedoary oil Zineol C10H18O 154.253 154.1357652 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane eucalyptol 470-82-6 CC12CCC(CC1)C(C)(C)O2 InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3 WEEGYLXZBRQIMU-UHFFFAOYSA-N belongs to the class of organic compounds known as oxanes. Oxanes are compounds containing an oxane (tetrahydropyran) ring, which is a six-member saturated aliphatic heterocycle with one oxygen atom and five carbon atoms. Oxanes Organic compounds Organoheterocyclic compounds Oxanes Aliphatic heteropolycyclic compounds Dialkyl ethers Hydrocarbon derivatives Oxacyclic compounds Aliphatic heteropolycyclic compound Dialkyl ether Ether Hydrocarbon derivative Organic oxygen compound Organooxygen compound Oxacycle Oxane Cyclic monoterpenes Menthane monoterpenoids Menthane monoterpenoids a monoterpenoid Liquid logp 3.36 ALOGPS logs -3.84 ALOGPS solubility 2.25e-02 g/l ALOGPS melting_point Mp 1.5° logp 2.35 ChemAxon pka_strongest_basic -4.2 ChemAxon iupac 1,3,3-trimethyl-2-oxabicyclo[2.2.2]octane ChemAxon average_mass 154.253 ChemAxon mono_mass 154.1357652 ChemAxon smiles CC12CCC(CC1)C(C)(C)O2 ChemAxon formula C10H18O ChemAxon inchi InChI=1S/C10H18O/c1-9(2)8-4-6-10(3,11-9)7-5-8/h8H,4-7H2,1-3H3 ChemAxon inchikey WEEGYLXZBRQIMU-UHFFFAOYSA-N ChemAxon polar_surface_area 9.23 ChemAxon refractivity 45.86 ChemAxon polarizability 18.54 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::NmrTwoD 1935 Specdb::NmrOneD 2000 Specdb::NmrOneD 277618 Specdb::NmrOneD 277619 Specdb::NmrOneD 277620 Specdb::NmrOneD 277621 Specdb::NmrOneD 277622 Specdb::NmrOneD 277623 Specdb::NmrOneD 277624 Specdb::NmrOneD 277625 Specdb::NmrOneD 277626 Specdb::NmrOneD 277627 Specdb::NmrOneD 277628 Specdb::NmrOneD 277629 Specdb::NmrOneD 277630 Specdb::NmrOneD 277631 Specdb::NmrOneD 277632 Specdb::NmrOneD 277633 Specdb::NmrOneD 277634 Specdb::NmrOneD 277635 Specdb::NmrOneD 277636 Specdb::NmrOneD 277637 Specdb::CMs 5566 Specdb::CMs 103754 Specdb::MsMs 2391 Specdb::MsMs 2392 Specdb::MsMs 2393 Specdb::MsMs 239689 Specdb::MsMs 239690 Specdb::MsMs 239691 Specdb::MsMs 241744 Specdb::MsMs 241745 Specdb::MsMs 241746 HMDB04472 27961 #<Reference:0x000055ce30abf5a0> #<Reference:0x000055ce30abf370> #<Reference:0x000055ce30abf190> #<Reference:0x000055ce30abef60> #<Reference:0x000055ce30abebf0> #<Reference:0x000055ce30abe9c0> #<Reference:0x000055ce30abe808> #<Reference:0x000055ce30abe650> #<Reference:0x000055ce30abe470> #<Reference:0x000055ce30abe1f0> #<Reference:0x000055ce30abd250> Allspice Type 1 specific Pimenta dioica 375272 37.05 69.0 5.1 mg/100 g Bilberry Type 1 specific Vaccinium myrtillus 180763 Blackcurrant Type 1 specific Ribes nigrum 78511 Caraway Type 1 specific Carum carvi 48032 Cardamom Type 1 specific Elettaria cardamomum 105181 Ceylon cinnamon Type 1 specific Cinnamomum verum 128608 48.25 48.25 48.25 mg/100 g Chinese cinnamon Type 1 specific Cinnamomum aromaticum 119260 Common oregano Type 1 specific Origanum vulgare 39352 3.35 5.0 1.7 mg/100 g Common sage Type 1 specific Salvia officinalis 38868 331.325 333.9 328.75 mg/100 g Common thyme Type 1 specific Thymus vulgaris 49992 230.0 230.0 230.0 mg/100 g Coriander Type 1 specific Coriandrum sativum 4047 Corn Type 1 specific Zea mays 4577 Cornmint Type 1 specific Mentha arvensis 292239 91.25 91.25 91.25 mg/100 g Cucumber Type 1 specific Cucumis sativus 3659 Cumin Type 1 specific Cuminum cyminum 52462 8.9 8.9 8.9 mg/100 g Dill Type 1 specific Anethum graveolens 40922 Fennel Type 1 specific Foeniculum vulgare 48038 15.05 15.05 15.05 mg/100 g Ginger Type 1 specific Zingiber officinale 94328 251.65 251.65 251.65 mg/100 g Herbs and Spices Unknown generic Highbush blueberry Type 1 specific Vaccinium corymbosum 69266 Hyssop Type 1 specific Hyssopus officinalis 39324 54.9 54.9 54.9 mg/100 g Lemon Type 1 specific Citrus limon 2708 Lemon grass Type 1 specific Cymbopogon citratus 66014 Lime Type 1 specific Citrus aurantiifolia 159033 7.0 7.0 7.0 mg/100 g Lovage Type 1 specific Levisticum officinale 48042 Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 3.8 3.8 3.8 mg/100 g Mugwort Type 1 specific Artemisia vulgaris 4220 Nutmeg Type 1 specific Myristica fragrans 51089 198.0 198.0 198.0 mg/100 g Orange mint Type 1 specific Mentha aquatica 190902 53.8 98.35 9.25 mg/100 g 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 69.6 69.6 69.6 mg/100 g Pitanga Type 1 specific Eugenia uniflora 119951 Pot marjoram Type 1 specific Origanum onites 452416 1.15 2.3 0.0 mg/100 g Roman camomile Type 1 specific Chamaemelum nobile 99037 Roselle Type 1 specific Hibiscus sabdariffa 183260 Rosemary Type 1 specific Rosmarinus officinalis 39367 227.966667 486.4 18.0 mg/100 g Saffron Type 1 specific Crocus sativus 82528 Spearmint Type 1 specific Mentha spicata 29719 510.375 548.0 472.75 mg/100 g Star anise Type 1 specific Illicium verum 124778 175.05 175.05 175.05 mg/100 g Summer savory Type 1 specific Satureja hortensis 49987 Sunflower Type 1 specific Helianthus annuus 4232 Sweet basil Type 1 specific Ocimum basilicum 39350 45.55 45.55 45.55 mg/100 g Sweet bay Type 1 specific Laurus nobilis 85223 768.75 768.75 768.75 mg/100 g Sweet marjoram Type 1 specific Origanum majorana 268884 Tarragon Type 1 specific Artemisia dracunculus 72341 27.5 27.5 27.5 mg/100 g Turmeric Type 1 specific Curcuma longa 136217 1144.416667 2920.0 33.0 mg/100 g Watermelon Type 1 specific Citrullus lanatus 3654 White mustard Type 1 specific Sinapis alba 3728 Winter savory Type 1 specific Satureja montana 49988 7.7 7.7 7.7 mg/100 g camphor eucalyptus herbal mint pepper sweet (-)-chronotropic 2 (-)-inotropic 3 Acaricide 16 A substance used to destroy pests of the subclass Acari (mites and ticks). Allelopathic 42 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. Anesthetic 62 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 bacterial 145 A substance that kills or slows the growth of bacteria. Anti cariogenic 165 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti cholinesterase 184 An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of cholinesterase (EC 3.1.1.8). Anti halitosic 314 Anti laryngitic 386 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti nociceptive 484 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. Anti septic 603 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti ulcer 676 One of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract. Anti-allergic 103 A drug used to treat allergic reactions. Anti-bronchitic 154 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-catarrh 169 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-fatigue 274 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-helmintic 72 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. Anti-inflammatory 370 A substance that reduces or suppresses inflammation. Anti-pharyngitic 526 Anti-plaque 531 Anti-rheumatic 585 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-rhinitic 587 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-sinusitic 617 Anti-spasmodic 619 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Anti-staphylococcic 627 A substance that kills or slows the growth of bacteria. Anti-tussive 674 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Candidicide 756 Carcinogenic 762 A role played by a chemical compound which is known to induce a process of carcinogenesis by corrupting normal cellular pathways, leading to the acquistion of tumoral capabilities. Central nervous system stimulant 816 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system. Choleretic 801 Convulsant 832 Counterirritant 839 Cytochrome-p450 inducer 854 Decongestant 862 A drug used to relieve nasal congestion in the upper respiratory tract. Degranulant 863 Dentifrice 869 Edemagenic 896 Expectorant 925 Any substance introduced into a living organism with therapeutic or diagnostic purpose. Fungicide 940 A substance used to destroy fungal pests. Gastroprotective 947 A drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion. Gram(-)icide 963 A substance that kills or slows the growth of bacteria. Gram(+)icide 962 A substance that kills or slows the growth of bacteria. Hepatotonic 983 Herbicide 986 A substance used to destroy plant pests. Hypotensive 1021 Inflammatory 1034 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. Irritant 1055 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). Neurotoxic 1160 A poison that interferes with the functions of the nervous system. Pediculicide 1202 Substance used to treat lice (genus Pediculus) infestation. Perfume 1205 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell. 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. Rubefacient 1301 Secretogogue 1308 Sedative 1311 A central nervous system depressant used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. Spasmogenic 1320 Surfactant 1340 A substance which lowers the surface tension of the medium in which it is dissolved, and/or the interfacial tension with other phases, and, accordingly, is positively adsorbed at the liquid/vapour and/or at other interfaces. Testosterone-hydroxylase inducer 1352 Transdermal 1374 Trichomonicide 1379