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

CAS: 25522-96-7 C21 H30 O5 MW: 362.46610000

Identification

Nameisohumulone
IUPAC3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
CAS Number25522-96-7
EINECS247-072-1
FDA UNIIE2S413495Y
Molecular FormulaC21 H30 O5
Molecular Weight362.46610000
Nikkaji NumberJ130.680D

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 ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for isohumulone usage levels up tonot for fragrance use.
Recommendation for isohumulone flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

beer PMC hop

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.