| Description | 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 ( Ref:DOI ). It contributes to the characteristic aroma of Cannabis (PMID: 6991645 ) and 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 is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ). 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 ).  |
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| Synonyms | | Value | Source |
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| (1E,4E,8E)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene | HMDB | | (1E,4E,8E)-2,6,6,9-Tetramethylcycloundeca-1,4,8-triene | HMDB | | (1E,4E,8E)-alpha-Humulene | HMDB | | (1E,4E,8E)-Humula-1(11),4,8-triene | HMDB | | (e,e,e)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene | HMDB | | 2,6,6,9-Tetramethyl-(1E,4E,8E)-1,4,8-cycloundecatriene | HMDB | | 2,6,6,9-Tetramethyl-(e,e,e)-1,4,8-cycloundecatriene | HMDB | | 2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene | HMDB | | 2,6,6,9-Tetramethyl-cycloundeca-1,4,8-triene | HMDB | | 3,7,10-Humulatriene | HMDB | | a-Caryophyllene (obsol.) | HMDB | | a-Humulene | HMDB, Generator | | alpha -Humulen | HMDB | | alpha -Humulene | HMDB | | alpha -Humulene (alpha -caryophyllene) | HMDB | | alpha -Humulenen | HMDB | | alpha-Caryophyllene | HMDB | | Humulene | HMDB | | alpha-Humulene | MeSH | | Α-humulene | Generator |
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| InChI Identifier | 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- |
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