EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

colupulone
3,5-dihydroxy-4-isobutyryl-2,6,6-tris-(3-methyl-but-2-enyl)-cyclohexa-2,4-dienone

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CAS Number: 468-27-9Picture of molecule3D/inchi
FDA UNII: Search
Nikkaji Web:J619.530J
XlogP3-AA:6.50 (est)
Molecular Weight:400.55872000
Formula:C25 H36 O4
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
Google Scholar: with word "volatile"Search
Google Scholar: with word "flavor"Search
Google Scholar: with word "odor"Search
Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 573.00 to 574.00 °C. @ 760.00 mm Hg (est)
Flash Point: 599.00 °F. TCC ( 314.90 °C. ) (est)
logP (o/w): 6.039 (est)
Soluble in:
 water, 0.003693 mg/L @ 25 °C (est)
Insoluble in:
 water
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Colupulone > 95%
Odor: characteristic
Use: Colupulone is a bitter acid extracted from HOPS.
Hopsteiner
Beta Bio
Antibacterial
Sigma-Aldrich: Sigma
For experimental / research use only.
Colupulone mixture of homologues, ≥85% (HPLC)
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for colupulone usage levels up to:
 not for fragrance use.
 
Recommendation for colupulone flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA Substance Registry Services (TSCA):468-27-9
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :373677
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
Chemidplus:0000468279
 
References:
 3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):373677
Pubchem (sid):135227072
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
CHEMBL:View
HMDB (The Human Metabolome Database):HMDB30065
FooDB:FDB001374
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 hop
Search Trop Picture
 
Synonyms:
 beta bio
 co-lupulone
2,4-cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(2-methyl-1-oxopropyl)-
2,4-cyclohexadien-1-one, 3,5-dihydroxy-4,6,6-tris(3-methyl-2-buten-1-yl)-2-(2-methyl-1-oxopropyl)-
3,5-dihydroxy-2-isobutyryl-4,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(2-methyl-1-oxopropyl)-2,4-cyclohexadien-1-one
3,5-dihydroxy-4-isobutyryl-2,6,6-tris-(3-methyl-but-2-enyl)-cyclohexa-2,4-dienone
3,5-dihydroxy-4,6,6-tris(3-methylbut-2-en-1-yl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
 

Articles:

PubMed:Synthesis and P-glycoprotein induction activity of colupulone analogs.
PubMed:Vibrational spectroscopy and chemometrics for rapid, quantitative analysis of bitter acids in hops (Humulus lupulus).
PubMed:Simultaneous determination of prenylflavonoid and hop bitter acid in beer lee by HPLC-DAD-MS.
PubMed:Hop bitter acids inhibit tumorigenicity of hepatocellular carcinoma cells in vitro.
PubMed:[Analysis of six acidic components in hops extracts by high performance liquid chromatography].
PubMed:Prenylated acylphloroglucinol derivatives: isoprenomics-based design, syntheses and antioxidative activities.
PubMed:Evaluation of genetic variability of wild hops (Humulus lupulus L.) in Canada and the Caucasus region by chemical and molecular methods.
PubMed:Identification and RP-HPLC-ESI-MS/MS quantitation of bitter-tasting beta-acid transformation products in beer.
PubMed:Antilisterial activity of hops beta acids in broth with or without other antimicrobials.
PubMed:Structural basis of human pregnane X receptor activation by the hops constituent colupulone.
PubMed:Determination of xanthohumol in hops (Humulus lupulus L.) by nonaqueous CE.
PubMed:Hexahydrocolupulone and its antitumor cell proliferation activity in vitro.
PubMed:Murine cytochrome P4503A is induced by 2-methyl-3-buten-2-ol, 3-methyl-1-pentyn-3-ol(meparfynol), and tert-amyl alcohol.
PubMed:The effect of colupulone (a HOPS beta-acid) on hepatic cytochrome P-450 enzymatic activity in the rat.
PubMed: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.
PubMed:Application of in vivo bioluminescence to the study of ionophoretic action.
PubMed:Factors affecting antibacterial activity of hop compounds and their derivatives.
PubMed:Identification of the antibiotic hops component, colupulone, as an inducer of hepatic cytochrome P-4503A in the mouse.
 
Notes:
an antibiotic hops component; induces hepatic cytochrome p-4503a in the mouse. Constit. of the resin of English hops
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