lupulon
2,4-cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-
Identification
| Name | lupulon |
| IUPAC | 3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one |
| CAS Number | 468-28-0 |
| EINECS | 207-405-3 |
| FDA UNII | B7425USG94 |
| Molecular Formula | C26 H38 O4 |
| Molecular Weight | 414.58566000 |
| MDL Number | MFCD00075970 |
| Nikkaji Number | J5.920J |
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 Toxicity | oral-rat LD50 100 mg/kg |
| Dermal Toxicity | subcutaneous-mouse LD50 600 mg/kg |
| 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 lupulon usage levels up to | not for fragrance use. |
| Recommendation for lupulon flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
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.).