2,4-cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-

CAS: 468-28-0 C26 H38 O4 MW: 414.58566000

Identification

Namelupulon
IUPAC3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
CAS Number468-28-0
EINECS207-405-3
FDA UNIIB7425USG94
Molecular FormulaC26 H38 O4
Molecular Weight414.58566000
MDL NumberMFCD00075970
Nikkaji NumberJ5.920J

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 93.00 °C. @ 760.00 mm Hg
Boiling Point 583.00 to 584.00 °C. @ 760.00 mm Hg (est)
Flash Point 610.00 °F. TCC ( 321.00 °C. ) (est)
logP (o/w) 6.548 (est)
Soluble in water, 0.002016 mg/L @ 25 °C (est)
Insoluble in water

No sensory data available

Safety Information

Oral/Parenteral Toxicityoral-rat LD50 100 mg/kg
Dermal Toxicitysubcutaneous-mouse LD50 600 mg/kg
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 lupulon usage levels up tonot for fragrance use.
Recommendation for lupulon flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

hop

Synonyms

b- bitter acid beta- bitter acid 2,4- cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)- 2,4- cyclohexadien-1-one, 3,5-dihydroxy-4-isovaleryl-2,6,6-tris(3-methyl-2-butenyl)- 3,5- dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one 3,5- dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one 3,5- dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one b- lupulic acid lupulone PubMed: Antituberculous activity and toxicity of lupulon for the mouse. PubMed: Lupulon, an antibiotic extracted from the strobiles of Humulus lupulus. PubMed: EFFECT OF ANTIBIOTIC DRUGS ON ANTISTAPHYLOCOCCAL ACTIVITY OF LUPULON AND HEXAHYDROLUPULON. PubMed: Tolerance and effects of lupulon in man. PubMed: FACTORS INFLUENCING THE ANTIBIOTIC ACTIVITY OF LUPULON. PubMed: Protection of Lupulon and Humulon by Ascorbic Acid. PubMed: Antifungal activity of hop resin constituents and a new method for isolation of lupulon. PubMed: [Lupulon and humulon, their antibacterial effects and therapeutic use in tuberculous infections]. PubMed: [Effect of lupulon in experimental tuberculosis of mice]. PubMed: Lupulon and humulon, antibiotic constituents of hops. PubMed: LUPULON AND HUMULON-ANTIBIOTIC CONSTITUENTS OF HOPS. PubMed: An investigation into the anticancer effects and mechanism of action of hop β-acid lupulone and its natural and synthetic derivatives in prostate cancer cells. PubMed: The effects of beta acids from hops (Humulus lupulus) on mortality of Varroa destructor (Acari: Varroidae). PubMed: On the reaction of lupulones, hops β-acids, with 1-hydroxyethyl radical. PubMed: Hop bitter acids inhibit tumorigenicity of hepatocellular carcinoma cells in vitro. PubMed: HlPT-1, a membrane-bound prenyltransferase responsible for the biosynthesis of bitter acids in hops. PubMed: Chicken intestine microbiota following the administration of lupulone, a hop-based antimicrobial. PubMed: Application of plant-based antimicrobials for the growth inhibition of clostridia in pressed beet pulp silage. PubMed: Lupulone triggers p38 MAPK-controlled activation of p53 and of the TRAIL receptor apoptotic pathway in human colon cancer-derived metastatic cells. PubMed: Early modulation of gene expression used as a biomarker for chemoprevention in a preclinical model of colon carcinogenesis. PubMed: In vitro evaluation of antibacterial, anticollagenase, and antioxidant activities of hop components (Humulus lupulus) addressing acne vulgaris. PubMed: Capillary zone electrophoresis method for determination of bitter (alpha- and beta-) acids in hop (Humulus lupulus L.) cone extracts. PubMed: Antilisterial activity of hops beta acids in broth with or without other antimicrobials. PubMed: Lupulone, a hop bitter acid, activates different death pathways involving apoptotic TRAIL-receptors, in human colon tumor cells and in their derived metastatic cells. PubMed: Antimicrobial activity of lupulone against Clostridium perfringens in the chicken intestinal tract jejunum and caecum. PubMed: Positive antibacterial co-action between hop (Humulus lupulus) constituents and selected antibiotics. PubMed: Antiangiogenic properties of lupulone, a bitter acid of hop cones. PubMed: Antioxidative activity of hop bitter acids and their analogues. PubMed: [Detection of sedative-hypnotic active ingredients in hops. 5. Degradation of bitter acids to 2-methyl-3-buten-2-ol, a hop constituent with sedative-hypnotic activity]. PubMed: Antagonistic effect of serum on bacteriostatic action of lupulone. PubMed: Chemopreventive effects of lupulone, a hop {beta}-acid, on human colon cancer-derived metastatic SW620 cells and in a rat model of colon carcinogenesis. PubMed: Prenylflavonoids and phloroglucinol derivatives from hops (Humulus lupulus). PubMed: Formation and accumulation of alpha-acids, beta-acids, desmethylxanthohumol, and xanthohumol during flowering of hops (Humulus lupulus L.).