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alpha-Humulene (FDB015360)

Record Information
Version1.0
Creation date2010-04-08 22:11:48 UTC
Update date2020-09-17 15:30:33 UTC
Primary IDFDB015360
Secondary Accession NumbersNot Available
Chemical Information
FooDB Namealpha-Humulene
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 ( 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).
CAS Number6753-98-6
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.011 g/LALOGPS
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
Chemical FormulaC15H24
IUPAC name(1Z,4Z,8Z)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene
InChI IdentifierInChI=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
Isomeric SMILESC\C1=C\CC(C)(C)\C=C/C\C(C)=C/CC1
Average Molecular Weight204.3511
Monoisotopic Molecular Weight204.187800768
Classification
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:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 88.16%; H 11.84%DFC
Melting Point< 25 oC
Boiling PointBp10 123°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSalpha-Humulene, non-derivatized, GC-MS Spectrumsplash10-0006-9300000000-96e2ddad1a99d808b4ddSpectrum
Predicted GC-MSalpha-Humulene, 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-d1375940e9b7ed7922b42016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-2930000000-cdb29a58477970796a702016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kr-4900000000-788e8bfc0021846819ae2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-8ecbabe7146ad27627522016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0390000000-984bd28446d79854bd712016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01ri-1900000000-139cbaab33ea7f90de6c2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0090000000-7ccf03fa1149a1e9f55f2021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-0920000000-90d0407fa9aa4598cee32021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-c084f3d998cc56a199d62021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0190000000-0612dd5822c06422c9bb2021-10-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0079-0900000000-358d2a7dc14a6841b1df2021-10-22View Spectrum
NMRNot Available
ChemSpider ID5006149
ChEMBL IDNot Available
KEGG Compound IDC09684
Pubchem Compound ID6508206
Pubchem Substance IDNot Available
ChEBI ID5768
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB36467
CRC / DFC (Dictionary of Food Compounds) IDJZV54-F:JZV54-F
EAFUS IDNot Available
Dr. Duke IDALPHA-CARYOPHYLLENE|ALPHA-HUMULENE|HUMULENE
BIGG IDNot Available
KNApSAcK IDC00003147
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID6753-98-6
GoodScent IDrw1027221
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti plasmodial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
antitumor35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
wood
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.