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isohumulone
3,4-dihydroxy-5-(3-methyl but-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl) cyclopent-2-en-1-one

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Name:3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
CAS Number: 25522-96-7Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:247-072-1
FDA UNII: E2S413495Y
Nikkaji Web:J130.680D
XlogP3-AA:3.80 (est)
Molecular Weight:362.46610000
Formula:C21 H30 O5
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Google Patents:Search
US Patents:Search
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Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 530.00 to 531.00 °C. @ 760.00 mm Hg (est)
Flash Point: 552.00 °F. TCC ( 288.70 °C. ) (est)
logP (o/w): 6.029 (est)
Soluble in:
 alcohol
 water, 17.45 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.
3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
 
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 isohumulone usage levels up to:
 not for fragrance use.
 
Recommendation for isohumulone flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :93090
National Institute of Allergy and Infectious Diseases:Data
3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
Chemidplus:0025522967
 
References:
 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):93090
Pubchem (sid):135050120
 
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
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 beer
Search PMC Picture
 hop
Search Trop Picture
 
Synonyms:
3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
3,4-dihydroxy-5-(3-methyl but-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl) cyclopent-2-en-1-one
 

Articles:

PubMed:Oxidation of isohumulones induces the formation of carboxylic acids by hydrolytic cleavage.
PubMed:Prediction of the ageing of commercial lager beer during storage based on the degradation of iso-α-acids.
PubMed:Bioavailability of hop-derived iso-α-acids and reduced derivatives.
PubMed:Comprehensive sensomics analysis of hop-derived bitter compounds during storage of beer.
PubMed:On the autoxidation of bitter-tasting iso-alpha-acids in beer.
PubMed:Isohumulones, the bitter component of beer, improve hyperglycemia and decrease body fat in Japanese subjects with prediabetes.
PubMed:NMR assignment of iso-alpha-acids from isomerised extracts of Humulus lupulus L. cones.
PubMed:Isohumulones derived from hops ameliorate renal injury via an anti-oxidative effect in Dahl salt-sensitive rats.
PubMed:Spectrophotometric method for exploring 3-methyl-2-butene-1-thiol (MBT) formation in lager.
PubMed:Effect of membrane lateral pressure on the expression of fructosyltransferases in Lactobacillus reuteri.
PubMed:Isohumulones modulate blood lipid status through the activation of PPAR alpha.
PubMed:Dietary supplement of isohumulones inhibits the formation of aberrant crypt foci with a concomitant decrease in prostaglandin E2 level in rat colon.
PubMed:Dietary isohumulones, the bitter components of beer, raise plasma HDL-cholesterol levels and reduce liver cholesterol and triacylglycerol contents similar to PPARalpha activations in C57BL/6 mice.
PubMed:Fate of flavins in sensitized photodegradation of isohumulones and reduced derivatives: studies on formation of radicals via EPR combined with detailed product analyses.
PubMed:Prevention of diet-induced obesity by dietary isomerized hop extract containing isohumulones, in rodents.
PubMed:Photooxidative degradation of beer bittering principles: a key step on the route to lightstruck flavor formation in beer.
PubMed:Isohumulones, bitter acids derived from hops, activate both peroxisome proliferator-activated receptor alpha and gamma and reduce insulin resistance.
PubMed:Radicaloid-type oxidative decomposition of beer bittering agents revealed.
PubMed:Photolysis of hop-derived trans-iso-alpha-acids and trans-tetrahydroiso-alpha-acids: product identification in relation to the lightstruck flavour of beer.
PubMed:Purification and partial characterization of an antigen specific to Lactobacillus brevis strains with beer spoilage activity.
PubMed:Chemoreception and perception of the bitterness of isohumulones.
PubMed:Genetics of bitter perception in 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:Membrane leakage in Bacillus subtilis 168 induced by the hop constituents lupulone, humulone, isohumulone and humulinic acid.
PubMed:Low antibiotic potency of isohumulone.
 
Notes:
None found
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