1.0 2010-04-08 22:11:48 UTC 2020-09-17 15:30:33 UTC FDB015360 alpha-Humulene alpha-humulene also known as Humulene or alpha-caryophyllene is a volatile organic compound that belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA; PMID:17467679), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP; PMID:23746261) pathway in the cytoplasm. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Humulene is is a pale yellowish green clear liquid, soluble in alcohol that is barely soluble in water. It has a woody odor and adds a woody, oceanic-watery, spicy-clove note to perfumes ( http://www.thegoodscentscompany.com/data/rw1027221.html#tooccur). It contributes to the taste of the spice Persicaria odorata or Vietnamese coriander. Humulene is found in hops (Humulus lupulus; doi:10.1055/s-2006-962205), from which its name was derived. It is often found together with its isomer beta-caryophyllene in many other aromatic plants such pine trees ( PMID: 17396639), orange trees, marsh elders, tobacco, sunflowers, Salvia officinalis (common sage, culinary sage), Lindera strychnifolia Uyaku (Japanese spicebush, ginseng species and the Zingiberaceae (the ginger family). alpha-humulene, a very reactive volatile organic compound emitted by many organic plants, quickly combines with ozone in sunlight (photooxidation) to create secondary organic aerosols ( oi:10.1039/c0cp02379e). alpha-humulene has antibacterial and anti-biofilm properties against Bacteroides fragilis (PMID: 32073898) and demonstrated anti-inflammatory properties in an ovalbumin-induced model of airway allergic inflammation (PMID: 19438512). (1E,4E,8E)-2,6,6,9-tetramethyl-1,4,8-cycloundecatriene (1E,4E,8E)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene (1E,4E,8E)-alpha-humulene (1E,4E,8E)-humula-1(11),4,8-triene (E,E,E)-2,6,6,9-tetramethyl-1,4,8-cycloundecatriene &alpha;-humulen &alpha;-humulene &alpha;-humulene (&alpha;-caryophyllene) &alpha;-humulenen 1,4,8-Cycloundecatriene, 2,6,6,9-tetramethyl-, (1E,4E,8E)- 1,4,8-Cycloundecatriene, 2,6,6,9-tetramethyl-, (E,E,E)- 2,6,6,9-Tetramethyl-(1e,4e,8e)-1,4,8-cycloundecatriene 2,6,6,9-Tetramethyl-(e,e,e)-1,4,8-cycloundecatriene 2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene 2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene (E,E,E)- 2,6,6,9-tetramethyl-cycloundeca-1,4,8-triene 3,7,10-Humulatriene a-Caryophyllene (obsol.) a-Humulene alpha -Humulen alpha -Humulene alpha -Humulene (alpha -caryophyllene) alpha -Humulenen Alpha-caryophyllene alpha-Humulene Cycloundeca-1,4,8-triene,2,6,6,9-tetramethyl- Humulene C15H24 204.3511 204.187800768 (1Z,4Z,8Z)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene humulene 6753-98-6 C\C1=C\CC(C)(C)\C=C/C\C(C)=C/CC1 InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6-,13-7-,14-10- FAMPSKZZVDUYOS-KXWHQPPKSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Humulane sesquiterpenoid Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 6.07 ALOGPS logs -4.28 ALOGPS solubility 1.08e-02 g/l ALOGPS melting_point < 25 oC logp 4.88 ChemAxon iupac (1Z,4Z,8Z)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene ChemAxon average_mass 204.3511 ChemAxon mono_mass 204.187800768 ChemAxon smiles C\C1=C\CC(C)(C)\C=C/C\C(C)=C/CC1 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-13-7-5-8-14(2)10-12-15(3,4)11-6-9-13/h6-7,10-11H,5,8-9,12H2,1-4H3/b11-6-,13-7-,14-10- ChemAxon inchikey FAMPSKZZVDUYOS-KXWHQPPKSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 71.55 ChemAxon polarizability 26.18 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 26064 Specdb::CMs 103775 Specdb::MsMs 110244 Specdb::MsMs 110245 Specdb::MsMs 110246 Specdb::MsMs 177870 Specdb::MsMs 177871 Specdb::MsMs 177872 Specdb::MsMs 3609967 Specdb::MsMs 3609968 Specdb::MsMs 3609969 Specdb::MsMs 3611104 Specdb::MsMs 3611105 Specdb::MsMs 3611106 HMDB36467 5768 #<Reference:0x000055ac3f47b7d8> #<Reference:0x000055ac3f47b620> Allspice Type 1 specific Pimenta dioica 375272 40.5 40.5 40.5 mg/100 g Beer Type 2 specific 0.05005 0.1 0.0001 mg/100 g Blackcurrant Type 1 specific Ribes nigrum 78511 0.4 0.4 0.4 mg/100 g Cardamom Type 1 specific Elettaria cardamomum 105181 Carrot Type 1 specific Daucus carota ssp. sativus 79200 1.2 1.2 1.2 mg/100 g Celery stalks Type 1 specific Apium graveolens var. dulce 117781 Ceylon cinnamon Type 1 specific Cinnamomum verum 128608 7.2 7.2 7.2 mg/100 g Chinese cinnamon Type 1 specific Cinnamomum aromaticum 119260 Cloves Type 1 specific Syzygium aromaticum 219868 1540.625 3000.0 81.25 mg/100 g Common oregano Type 1 specific Origanum vulgare 39352 19.1 19.1 19.1 mg/100 g Common sage Type 1 specific Salvia officinalis 38868 36.3 36.3 36.3 mg/100 g Cottonseed Type 1 specific Gossypium 3633 2540.0 2540.0 2540.0 mg/100 g Cucumber Type 1 specific Cucumis sativus 3659 Fennel Type 1 specific Foeniculum vulgare 48038 Garden tomato (var.) Type 1 specific Solanum lycopersicum var. lycopersicum 397755 Ginger Type 1 specific Zingiber officinale 94328 Guava Type 1 specific Psidium guajava 120290 Herbs and Spices Unknown generic Hyssop Type 1 specific Hyssopus officinalis 39324 13.9 34.0 0.65 mg/100 g Lemon Type 1 specific Citrus limon 2708 1.0 1.0 1.0 mg/100 g Lemon balm Type 1 specific Melissa officinalis 39338 4.05 4.05 4.05 mg/100 g Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 0.5 0.5 0.5 mg/100 g Nutmeg Type 1 specific Myristica fragrans 51089 Pepper (Spice) Type 1 specific Piper nigrum 13216 Pot marjoram Type 1 specific Origanum onites 452416 1.0 1.0 1.0 mg/100 g Roman camomile Type 1 specific Chamaemelum nobile 99037 Rosemary Type 1 specific Rosmarinus officinalis 39367 18.7525 36.255 1.25 mg/100 g Safflower Type 1 specific Carthamus tinctorius 4222 0.1465 0.18 0.113 mg/100 g Spearmint Type 1 specific Mentha spicata 29719 16.5 16.5 16.5 mg/100 g Star anise Type 1 specific Illicium verum 124778 45.05 45.05 45.05 mg/100 g Sugar apple Type 1 specific Annona squamosa 301693 Sweet basil Type 1 specific Ocimum basilicum 39350 16.45 16.45 16.45 mg/100 g Sweet bay Type 1 specific Laurus nobilis 85223 Sweet marjoram Type 1 specific Origanum majorana 268884 Sweet orange Type 1 specific Citrus sinensis 2711 Tamarind Type 1 specific Tamarindus indica 58860 Wild carrot Type 1 specific Daucus carota 4039 1.2 1.2 1.2 mg/100 g Wild celery Type 1 specific Apium graveolens 4045 138.3 138.3 138.3 mg/100 g Winter savory Type 1 specific Satureja montana 49988 16.65 16.65 16.65 mg/100 g wood woody anti malarial 416 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. anti plasmodial 532 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans. antitumor 672 A substance that inhibits or prevents the proliferation of neoplasms. perfumery 1206 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.