Record Information
Version1.0
Created at2020-03-18 23:24:51 UTC
Updated at2020-12-07 19:07:06 UTC
CannabisDB IDCDB000102
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameHumulene
Descriptionalpha-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 ). 
Structure
Thumb
Synonyms
ValueSource
a-HumuleneGenerator
Α-humuleneGenerator
(1E,4E,8E)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatrieneHMDB
(1E,4E,8E)-2,6,6,9-Tetramethylcycloundeca-1,4,8-trieneHMDB
(1E,4E,8E)-alpha-HumuleneHMDB
(1E,4E,8E)-Humula-1(11),4,8-trieneHMDB
(e,e,e)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatrieneHMDB
2,6,6,9-Tetramethyl-(1E,4E,8E)-1,4,8-cycloundecatrieneHMDB
2,6,6,9-Tetramethyl-(e,e,e)-1,4,8-cycloundecatrieneHMDB
2,6,6,9-Tetramethyl-1,4,8-cycloundecatrieneHMDB
2,6,6,9-Tetramethyl-cycloundeca-1,4,8-trieneHMDB
3,7,10-HumulatrieneHMDB
a-Caryophyllene (obsol.)HMDB
alpha -HumulenHMDB
alpha -HumuleneHMDB
alpha -Humulene (alpha -caryophyllene)HMDB
alpha -HumulenenHMDB
alpha-CaryophylleneHMDB
HumuleneHMDB
alpha-HumuleneMeSH
Chemical FormulaC15H24
Average Molecular Weight204.35
Monoisotopic Molecular Weight204.1878
IUPAC Name(1Z,4Z,8Z)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene
Traditional Namehumulene
CAS Registry Number6753-98-6
SMILES
C\C1=C\CC(C)(C)\C=C/C\C(C)=C/CC1
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-
InChI KeyFAMPSKZZVDUYOS-KXWHQPPKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
Alternative Parents
Substituents
  • Humulane sesquiterpenoid
  • Sesquiterpenoid
  • Branched unsaturated hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point106 - 107 °C at 5 mmHgWikipedia
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP6.07ALOGPS
logP4.88ChemAxon
logS-4.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity71.55 m³·mol⁻¹ChemAxon
Polarizability26.18 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSHumulene, non-derivatized, GC-MS Spectrumsplash10-0006-9300000000-96e2ddad1a99d808b4ddSpectrum
Predicted GC-MSHumulene, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000i-0920000000-3e5845e9275b1b3231faSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0290000000-d1375940e9b7ed7922b4Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2930000000-cdb29a58477970796a70Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-4900000000-788e8bfc0021846819aeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-8ecbabe7146ad2762752Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-984bd28446d79854bd71Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ri-1900000000-139cbaab33ea7f90de6cSpectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
8-Ball KushDetected and Quantified0.952 mg/g dry wt details
9 Lb HammerDetected and Quantified0.699 mg/g dry wt details
97 SageDetected and Quantified0.341 mg/g dry wt details
AdonisDetected and Quantified1.247 mg/g dry wt details
Alien Dawg (Indica dominant)Detected and Quantified0.79 +/- 0.01 mg/g dry wt
    • Jiamin Zheng, Yil...
details
Alien Sour AppleDetected and Quantified0.464 mg/g dry wt details
Animal CookiesDetected and Quantified3.2 +/- 0.7 mg/g dry wt details
Black BossDetected and Quantified0.471 mg/g dry wt details
Blue CookiesDetected and Quantified2.8 +/- 0.3 mg/g dry wt details
Blue DreamDetected and Quantified0.986 mg/g dry wt details
Blue DreamDetected and Quantified1.003 mg/g dry wt details
Blue DreamDetected and Quantified1.051 mg/g dry wt details
Blue DreamDetected and Quantified1.348 mg/g dry wt details
Blue DreamDetected and Quantified1.4 +/- 0.3 mg/g dry wt details
Bob MarleyDetected and Quantified0.159 mg/g dry wt details
Bubba KushDetected and Quantified1.8 +/- 1.1 mg/g dry wt details
ChemdawgDetected and Quantified1.714 mg/g dry wt details
Chemdawg #4Detected and Quantified1.615 mg/g dry wt details
Chemdawg #4Detected and Quantified4.327 mg/g dry wt details
ChemdogDetected and Quantified2.2 +/- 0.6 mg/g dry wt details
Cookies and CreamDetected and Quantified0.871 mg/g dry wt details
Cosmic LotusDetected and Quantified0.357 mg/g dry wt details
Crown OgDetected and Quantified1.1 +/- 0.3 mg/g dry wt details
Dairy QueenDetected and Quantified0.176 mg/g dry wt details
Dark Shadow HazeDetected and Quantified0.478 mg/g dry wt details
FLODetected and Quantified0.598 mg/g dry wt details
Fortune CookiesDetected and Quantified4 +/- 0.9 mg/g dry wt details
GasDetected and Quantified1.5 +/- 0.2 mg/g dry wt details
GelatoDetected and Quantified1.1 +/- 0.3 mg/g dry wt details
Girl Scout CookiesDetected and Quantified3.2 +/- 0.6 mg/g dry wt details
GodfatherDetected and Quantified0.5 +/- 0.2 mg/g dry wt details
Goji OGDetected and Quantified0.558 mg/g dry wt details
Golden CobraDetected and Quantified0.522 mg/g dry wt details
Golden SageDetected and Quantified0.912 mg/g dry wt details
Gorilla GlueDetected and Quantified2.404 mg/g dry wt details
Gorilla Glue #4Detected and Quantified1.81 mg/g dry wt details
Gorilla Glue #4Detected and Quantified2.5 +/- 0.5 mg/g dry wt details
Gorilla Glue #4Detected and Quantified1.810 mg/g dry wt details
Grape ApeDetected and Quantified1 +/- 0.1 mg/g dry wt details
Grape StomperDetected and Quantified0.582 mg/g dry wt details
Grape StomperDetected and Quantified0.62 mg/g dry wt details
Grape StomperDetected and Quantified0.620 mg/g dry wt details
Grizzly KushDetected and Quantified0.403 mg/g dry wt details
Hash PlantDetected and Quantified0.596 mg/g dry wt details
Hash PlantDetected and Quantified0.863 mg/g dry wt details
HemlockDetected and Quantified0.37 mg/g dry wt details
HemlockDetected and Quantified0.370 mg/g dry wt details
JabberwockyDetected and Quantified1.459 mg/g dry wt details
JabberwockyDetected and Quantified1.608 mg/g dry wt details
Jack HererDetected and Quantified0.391 mg/g dry wt details
Jack HererDetected and Quantified1.4 +/- 0.4 mg/g dry wt details
Kandy KushDetected and Quantified0.391 mg/g dry wt details
Kush PuppyDetected and Quantified0.562 mg/g dry wt details
La ChocoDetected and Quantified0.701 mg/g dry wt details
Lemon BalmDetected and Quantified0.611 mg/g dry wt details
Lemon GojiDetected and Quantified0.429 mg/g dry wt details
Lemon OGDetected and Quantified0.219 mg/g dry wt details
Lemon SherbetDetected and Quantified3.667 mg/g dry wt details
Lemon SkunkDetected and Quantified0.263 mg/g dry wt details
Lemon SkunkDetected and Quantified1.564 mg/g dry wt details
Liberty HazeDetected and Quantified0.611 mg/g dry wt details
LohanDetected and Quantified0.244 mg/g dry wt details
Lucky CharmsDetected and Quantified1.099 mg/g dry wt details
Master KushDetected and Quantified1.1 +/- 0.2 mg/g dry wt details
Maui HazeDetected and Quantified2.260 mg/g dry wt details
Maui HazeDetected and Quantified2.26 mg/g dry wt details
Miami White KushDetected and Quantified2 +/- 0.3 mg/g dry wt details
Moby DickDetected and Quantified0.904 mg/g dry wt details
Moonshine Ghost Trane HazeDetected and Quantified0.872 mg/g dry wt details
Mr. NiceDetected and Quantified0.8 +/- 0.5 mg/g dry wt details
Nightmare CookieDetected and Quantified1.217 mg/g dry wt details
Og KushDetected and Quantified1.5 +/- 0.4 mg/g dry wt details
Orange SkunkDetected and Quantified2.256 mg/g dry wt details
Pineapple SkunkDetected and Quantified1.231 mg/g dry wt details
Pipe DreamDetected and Quantified1.647 mg/g dry wt details
Platinum DelightDetected and Quantified1.273 mg/g dry wt details
Purple CreamDetected and Quantified1 +/- 0.2 mg/g dry wt details
Purple EclipseDetected and Quantified1.341 mg/g dry wt details
Purple PrincessDetected and Quantified1.1 +/- 0.3 mg/g dry wt details
Purple UrkleDetected and Quantified1 +/- 0.2 mg/g dry wt details
Rocket FuelDetected and Quantified2.022 mg/g dry wt details
Rollex OGDetected and Quantified0.922 mg/g dry wt details
Rosetta StoneDetected and Quantified0.934 mg/g dry wt details
SatoriDetected and Quantified0.179 mg/g dry wt details
Sensi Star (Pure Indica)Detected and Quantified0.18 +/- 0.00 mg/g dry wt
    • Jiamin Zheng, Yil...
details
SherbertDetected and Quantified2.7 +/- 0.8 mg/g dry wt details
Skunk HazeDetected and Quantified1.137 mg/g dry wt details
Skywalker OGDetected and Quantified0.934 mg/g dry wt details
Skywalker Og KushDetected and Quantified1.4 +/- 0.3 mg/g dry wt details
Sour DieselDetected and Quantified1.6 +/- 0.5 mg/g dry wt details
SpectrumDetected and Quantified0.586 mg/g dry wt details
Star BudDetected and Quantified0.692 mg/g dry wt details
Star KillerDetected and Quantified0.733 mg/g dry wt details
Strawberry FieldsDetected and Quantified0.542 mg/g dry wt details
Strawberry FieldsDetected and Quantified0.618 mg/g dry wt details
Strawberry HazeDetected and Quantified1.2 +/- 0.3 mg/g dry wt details
Sunset SherbetDetected and Quantified1.642 mg/g dry wt details
Superman Og KushDetected and Quantified1.3 +/- 0.2 mg/g dry wt details
Tahoe Og KushDetected and Quantified1.8 +/- 0.3 mg/g dry wt details
Tangerine DreamDetected and Quantified0.909 mg/g dry wt details
Tangerine Dream (Sativa dominant)Detected and Quantified0.22 +/- 0.01 mg/g dry wt
    • Jiamin Zheng, Yil...
details
The SauceDetected and Quantified1.553 mg/g dry wt details
Thin MintsDetected and Quantified3.4 +/- 1.1 mg/g dry wt details
TrainwreckDetected and Quantified0.5 +/- 0.3 mg/g dry wt details
Triple ODetected and Quantified1.4 +/- 0.2 mg/g dry wt details
Venom OGDetected and Quantified2.049 mg/g dry wt details
White WidowDetected and Quantified0.296 mg/g dry wt details
Wonder WomanDetected and Quantified0.616 mg/g dry wt details
HMDB IDHMDB0036467
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB015360
KNApSAcK IDC00003147
Chemspider ID5006149
KEGG Compound IDC09684
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkHumulene
METLIN IDNot Available
PubChem Compound6508206
PDB IDNot Available
ChEBI ID5768
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  2. Schramek N, Wang H, Romisch-Margl W, Keil B, Radykewicz T, Winzenhorlein B, Beerhues L, Bacher A, Rohdich F, Gershenzon J, Liu B, Eisenreich W: Artemisinin biosynthesis in growing plants of Artemisia annua. A 13CO2 study. Phytochemistry. 2010 Feb;71(2-3):179-87. doi: 10.1016/j.phytochem.2009.10.015. Epub 2009 Nov 22. [PubMed:19932496 ]
  3. Towler MJ, Weathers PJ: Evidence of artemisinin production from IPP stemming from both the mevalonate and the nonmevalonate pathways. Plant Cell Rep. 2007 Dec;26(12):2129-36. doi: 10.1007/s00299-007-0420-x. Epub 2007 Aug 21. [PubMed:17710406 ]
  4. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]
  5. Buhaescu I, Izzedine H: Mevalonate pathway: a review of clinical and therapeutical implications. Clin Biochem. 2007 Jun;40(9-10):575-84. doi: 10.1016/j.clinbiochem.2007.03.016. Epub 2007 Mar 31. [PubMed:17467679 ]
  6. Zhao L, Chang WC, Xiao Y, Liu HW, Liu P: Methylerythritol phosphate pathway of isoprenoid biosynthesis. Annu Rev Biochem. 2013;82:497-530. doi: 10.1146/annurev-biochem-052010-100934. [PubMed:23746261 ]
  7. Helmig D, Ortega J, Duhl T, Tanner D, Guenther A, Harley P, Wiedinmyer C, Milford J, Sakulyanontvittaya T: Sesquiterpene emissions from pine trees--identifications, emission rates and flux estimates for the contiguous United States. Environ Sci Technol. 2007 Mar 1;41(5):1545-53. doi: 10.1021/es0618907. [PubMed:17396639 ]
  8. Jang HI, Rhee KJ, Eom YB: Antibacterial and antibiofilm effects of alpha-humulene against Bacteroides fragilis. Can J Microbiol. 2020 Jun;66(6):389-399. doi: 10.1139/cjm-2020-0004. Epub 2020 Feb 19. [PubMed:32073898 ]
  9. Rogerio AP, Andrade EL, Leite DF, Figueiredo CP, Calixto JB: Preventive and therapeutic anti-inflammatory properties of the sesquiterpene alpha-humulene in experimental airways allergic inflammation. Br J Pharmacol. 2009 Oct;158(4):1074-87. doi: 10.1111/j.1476-5381.2009.00177.x. Epub 2009 May 8. [PubMed:19438512 ]