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
Identification
| Name | isohumulone |
| IUPAC | 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one |
| CAS Number | 25522-96-7 |
| EINECS | 247-072-1 |
| FDA UNII | E2S413495Y |
| Molecular Formula | C21 H30 O5 |
| Molecular Weight | 362.46610000 |
| Nikkaji Number | J130.680D |
Regulatory
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 |
| Insoluble in | water |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| 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. |
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Potential Uses
Natural Occurrence
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
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.