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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:34:31 UTC
Update Date2022-03-07 02:52:24 UTC
HMDB IDHMDB0030065
Secondary Accession Numbers
  • HMDB30065
Metabolite Identification
Common NameColupulone
DescriptionColupulone belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively. Based on a literature review a significant number of articles have been published on Colupulone.
Structure
Data?1563861931
Synonyms
ValueSource
CO-LupuloneHMDB
Chemical FormulaC25H36O4
Average Molecular Weight400.5509
Monoisotopic Molecular Weight400.26135964
IUPAC Name5-hydroxy-4,6,6-tris(3-methylbut-2-en-1-yl)-2-(2-methylpropanoyl)cyclohex-4-ene-1,3-dione
Traditional Name5-hydroxy-4,6,6-tris(3-methylbut-2-en-1-yl)-2-(2-methylpropanoyl)cyclohex-4-ene-1,3-dione
CAS Registry Number468-27-9
SMILES
CC(C)C(=O)C1C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O
InChI Identifier
InChI=1S/C25H36O4/c1-15(2)9-10-19-22(27)20(21(26)18(7)8)24(29)25(23(19)28,13-11-16(3)4)14-12-17(5)6/h9,11-12,18,20,28H,10,13-14H2,1-8H3
InChI KeyFJDKDBGVEXNOEZ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as m-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 3-position, respectively.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentM-benzoquinones
Alternative Parents
Substituents
  • M-benzoquinone
  • Cyclohexenone
  • 1,3-diketone
  • 1,3-dicarbonyl compound
  • Vinylogous acid
  • Enol
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effect
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point92 - 93 °CNot Available
Boiling Point573.00 to 574.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility0.0037 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP6.039 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.0052 g/LALOGPS
logP4.23ALOGPS
logP6.6ChemAxon
logS-4.9ALOGPS
pKa (Strongest Acidic)5.52ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area71.44 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity122.01 m³·mol⁻¹ChemAxon
Polarizability46.65 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+207.44730932474
DeepCCS[M-H]-205.08930932474
DeepCCS[M-2H]-238.92230932474
DeepCCS[M+Na]+214.15130932474
AllCCS[M+H]+198.832859911
AllCCS[M+H-H2O]+196.432859911
AllCCS[M+NH4]+200.932859911
AllCCS[M+Na]+201.532859911
AllCCS[M-H]-210.332859911
AllCCS[M+Na-2H]-211.232859911
AllCCS[M+HCOO]-212.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ColupuloneCC(C)C(=O)C1C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O3533.1Standard polar33892256
ColupuloneCC(C)C(=O)C1C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O2521.4Standard non polar33892256
ColupuloneCC(C)C(=O)C1C(=O)C(CC=C(C)C)=C(O)C(CC=C(C)C)(CC=C(C)C)C1=O2418.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Colupulone,1TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(=O)C(C)C)C1=O2649.2Semi standard non polar33892256
Colupulone,1TMS,isomer #2CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(=C(O[Si](C)(C)C)C(C)C)C1=O2646.6Semi standard non polar33892256
Colupulone,1TMS,isomer #3CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C)=C(C)C)C1=O2719.3Semi standard non polar33892256
Colupulone,1TMS,isomer #4CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(=O)C(C)C)=C1O[Si](C)(C)C2636.7Semi standard non polar33892256
Colupulone,1TMS,isomer #5CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C)=C(C(=O)C(C)C)C1=O2591.3Semi standard non polar33892256
Colupulone,2TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C)=C(C(=O)C(C)C)C1=O2652.2Semi standard non polar33892256
Colupulone,2TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C)=C(C(=O)C(C)C)C1=O2613.9Standard non polar33892256
Colupulone,2TMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C)=C(C)C)C1=O2736.3Semi standard non polar33892256
Colupulone,2TMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C)=C(C)C)C1=O2698.2Standard non polar33892256
Colupulone,2TMS,isomer #3CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(=C(O[Si](C)(C)C)C(C)C)C1=O2671.4Semi standard non polar33892256
Colupulone,2TMS,isomer #3CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(=C(O[Si](C)(C)C)C(C)C)C1=O2654.3Standard non polar33892256
Colupulone,2TMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(=O)C(C)C)=C1O[Si](C)(C)C2636.6Semi standard non polar33892256
Colupulone,2TMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(=O)C(C)C)=C1O[Si](C)(C)C2578.1Standard non polar33892256
Colupulone,2TMS,isomer #5CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C)=C(C(O[Si](C)(C)C)=C(C)C)C1=O2680.9Semi standard non polar33892256
Colupulone,2TMS,isomer #5CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C)=C(C(O[Si](C)(C)C)=C(C)C)C1=O2727.1Standard non polar33892256
Colupulone,2TMS,isomer #6CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C)=C(C)C)=C1O[Si](C)(C)C2721.8Semi standard non polar33892256
Colupulone,2TMS,isomer #6CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C)=C(C)C)=C1O[Si](C)(C)C2690.0Standard non polar33892256
Colupulone,3TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C)=C(C(O[Si](C)(C)C)=C(C)C)C1=O2724.8Semi standard non polar33892256
Colupulone,3TMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C)=C(C(O[Si](C)(C)C)=C(C)C)C1=O2725.9Standard non polar33892256
Colupulone,3TMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C)=C(C)C)=C1O[Si](C)(C)C2716.8Semi standard non polar33892256
Colupulone,3TMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C)=C(C)C)=C1O[Si](C)(C)C2690.5Standard non polar33892256
Colupulone,1TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(=O)C(C)C)C1=O2882.4Semi standard non polar33892256
Colupulone,1TBDMS,isomer #2CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(=C(O[Si](C)(C)C(C)(C)C)C(C)C)C1=O2884.7Semi standard non polar33892256
Colupulone,1TBDMS,isomer #3CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C1=O2955.6Semi standard non polar33892256
Colupulone,1TBDMS,isomer #4CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C2875.2Semi standard non polar33892256
Colupulone,1TBDMS,isomer #5CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)C(C)C)C1=O2830.7Semi standard non polar33892256
Colupulone,2TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)C(C)C)C1=O3114.0Semi standard non polar33892256
Colupulone,2TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(=O)C(C)C)C1=O3003.1Standard non polar33892256
Colupulone,2TBDMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C1=O3207.2Semi standard non polar33892256
Colupulone,2TBDMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C1=O3100.1Standard non polar33892256
Colupulone,2TBDMS,isomer #3CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(=C(O[Si](C)(C)C(C)(C)C)C(C)C)C1=O3156.8Semi standard non polar33892256
Colupulone,2TBDMS,isomer #3CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(=C(O[Si](C)(C)C(C)(C)C)C(C)C)C1=O3046.3Standard non polar33892256
Colupulone,2TBDMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C3113.3Semi standard non polar33892256
Colupulone,2TBDMS,isomer #4CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(=O)C(C)C)=C1O[Si](C)(C)C(C)(C)C2960.0Standard non polar33892256
Colupulone,2TBDMS,isomer #5CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C1=O3139.4Semi standard non polar33892256
Colupulone,2TBDMS,isomer #5CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C1=O3112.0Standard non polar33892256
Colupulone,2TBDMS,isomer #6CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C(C)(C)C)=C(C)C)=C1O[Si](C)(C)C(C)(C)C3183.2Semi standard non polar33892256
Colupulone,2TBDMS,isomer #6CC(C)=CCC1=C(O)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C(C)(C)C)=C(C)C)=C1O[Si](C)(C)C(C)(C)C3071.0Standard non polar33892256
Colupulone,3TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C1=O3359.7Semi standard non polar33892256
Colupulone,3TBDMS,isomer #1CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(O[Si](C)(C)C(C)(C)C)=C(C(O[Si](C)(C)C(C)(C)C)=C(C)C)C1=O3245.1Standard non polar33892256
Colupulone,3TBDMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C(C)(C)C)=C(C)C)=C1O[Si](C)(C)C(C)(C)C3354.9Semi standard non polar33892256
Colupulone,3TBDMS,isomer #2CC(C)=CCC1=C(O[Si](C)(C)C(C)(C)C)C(CC=C(C)C)(CC=C(C)C)C(=O)C(C(O[Si](C)(C)C(C)(C)C)=C(C)C)=C1O[Si](C)(C)C(C)(C)C3200.2Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Colupulone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0abl-9327000000-a2b2418ee20b5fe6fddc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Colupulone GC-MS (1 TMS) - 70eV, Positivesplash10-0adi-9212800000-543d9bdab1ac539cb8262017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Colupulone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Colupulone GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 10V, Positive-QTOFsplash10-0zgi-1009500000-52b8e86c723279aa24232016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 20V, Positive-QTOFsplash10-060s-5129100000-c030fa83408e9c3b98602016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 40V, Positive-QTOFsplash10-01c1-9412000000-3b26c444dbf1327835572016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 10V, Negative-QTOFsplash10-0002-0009000000-a04054665e36893c25e52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 20V, Negative-QTOFsplash10-004i-2119000000-ad0459861643e13eb6732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 40V, Negative-QTOFsplash10-001l-9638000000-580f03c6adcc955909862016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 10V, Positive-QTOFsplash10-0udi-0024900000-72d2446136763d553f0d2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 20V, Positive-QTOFsplash10-005j-1197100000-116abc9137f6242150942021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 40V, Positive-QTOFsplash10-00dl-5593000000-fbac3fb1d4cf793ef4c82021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 10V, Negative-QTOFsplash10-0002-0009000000-d15b9ee8f8913bd785052021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 20V, Negative-QTOFsplash10-0002-1009000000-6301a67ca942318388292021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Colupulone 40V, Negative-QTOFsplash10-0bt9-1692000000-31c4be746e41df1ca9a92021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001374
KNApSAcK IDC00053088
Chemspider ID35013126
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound57965774
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1038681
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Teotico DG, Bischof JJ, Peng L, Kliewer SA, Redinbo MR: Structural basis of human pregnane X receptor activation by the hops constituent colupulone. Mol Pharmacol. 2008 Dec;74(6):1512-20. doi: 10.1124/mol.108.050732. Epub 2008 Sep 2. [PubMed:18768384 ]
  2. Shipp EB, Mehigh CS, Helferich WG: The effect of colupulone (a HOPS beta-acid) on hepatic cytochrome P-450 enzymatic activity in the rat. Food Chem Toxicol. 1994 Nov;32(11):1007-14. [PubMed:7959454 ]
  3. Mannering GJ, Shoeman JA, Shoeman DW: Effects of colupulone, a component of hops and brewers yeast, and chromium on glucose tolerance and hepatic cytochrome P450 in nondiabetic and spontaneously diabetic mice. Biochem Biophys Res Commun. 1994 May 16;200(3):1455-62. [PubMed:8185600 ]
  4. Haseleu G, Intelmann D, Hofmann T: Identification and RP-HPLC-ESI-MS/MS quantitation of bitter-tasting beta-acid transformation products in beer. J Agric Food Chem. 2009 Aug 26;57(16):7480-9. doi: 10.1021/jf901759y. [PubMed:19627140 ]
  5. Patzak J, Nesvadba V, Krofta K, Henychova A, Marzoev AI, Richards K: Evaluation of genetic variability of wild hops (Humulus lupulus L.) in Canada and the Caucasus region by chemical and molecular methods. Genome. 2010 Jul;53(7):545-57. doi: 10.1139/g10-024. [PubMed:20616876 ]
  6. Stephan TE, Ngo EO, Nutter LM: Hexahydrocolupulone and its antitumor cell proliferation activity in vitro. Biochem Pharmacol. 1998 Feb 15;55(4):505-14. [PubMed:9514086 ]
  7. Simpson WJ: Application of in vivo bioluminescence to the study of ionophoretic action. J Biolumin Chemilumin. 1993 May-Jun;8(3):147-52. [PubMed:8493884 ]
  8. Simpson WJ, Smith AR: Factors affecting antibacterial activity of hop compounds and their derivatives. J Appl Bacteriol. 1992 Apr;72(4):327-34. [PubMed:1517174 ]
  9. Mannering GJ, Shoeman JA, Deloria LB: Identification of the antibiotic hops component, colupulone, as an inducer of hepatic cytochrome P-4503A in the mouse. Drug Metab Dispos. 1992 Mar-Apr;20(2):142-7. [PubMed:1352202 ]
  10. Mannering GJ, Shoeman JA: Murine cytochrome P4503A is induced by 2-methyl-3-buten-2-ol, 3-methyl-1-pentyn-3-ol(meparfynol), and tert-amyl alcohol. Xenobiotica. 1996 May;26(5):487-93. [PubMed:8736060 ]
  11. Cai X, Xia L, Sun Y, Li T, Xia M: [Analysis of six acidic components in hops extracts by high performance liquid chromatography]. Se Pu. 2011 Oct;29(10):983-7. [PubMed:22268354 ]
  12. Kac J, Zakrajsek J, Mlinaric A, Kreft S, Filipic M: Determination of xanthohumol in hops (Humulus lupulus L.) by nonaqueous CE. Electrophoresis. 2007 Mar;28(6):965-9. [PubMed:17309054 ]
  13. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .