| Identification | Back Directory | [Name]
HUMULONE* | [CAS]
26472-41-3 | [Synonyms]
HUMULONE
α-bitter acid
[R,(-)]-Humulone
HUMULONE USP/EP/BP
Phloroglucinol Impurity T
(R)-Humulone
DISCONTINUED
α-Bitter acid, α-Lupulic acid
Humulone, mixture of homologues
(6R)-3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienone
(6R)-4,6-Diprenyl-3,5,6-trihydroxy-2-(1-oxo-3-methylbutyl)-2,4-cyclohexadiene-1-one
(6R)-2-(3-Methylbutyryl)-3,5,6-trihydroxy-4,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadiene-1-one
(6S)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
[R,(-)]-3,5,6-Trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
2,4-Cyclohexadien-1-one,3,5,6-trihydroxy-4,6-bis(3-methyl-2-buten-1-yl)-2-(3-methyl-1-oxobutyl)-, (6R)- | [EINECS(EC#)]
247-725-0 | [Molecular Formula]
C21H30O5 | [MDL Number]
MFCD00076002 | [MOL File]
26472-41-3.mol | [Molecular Weight]
362.46 |
| Chemical Properties | Back Directory | [Melting point ]
65-66.5℃ | [alpha ]
D20 -212° (1.0 g in 15.5 g 96% alc) | [Boiling point ]
414.06°C (rough estimate) | [density ]
1.157±0.06 g/cm3 (20 ºC 760 Torr) | [refractive index ]
1.6120 (estimate) | [storage temp. ]
−20°C
| [solubility ]
DMSO : 100 mg/mL (275.89 mM; Need ultrasonic) | [form ]
Powder | [pka]
4.50±1.00(Predicted) | [color ]
Light yellow to yellow |
| Hazard Information | Back Directory | [Uses]
(R)-Humulone (CAS# 26471-41-3) can be used as a chemosensory receptor ligand. | [Definition]
ChEBI: Humulone is an optically active cyclic ketone consisting of 3,5,6-trihydroxycyclohexa-2,4-dien-1-one bearing two 3-methylbut-2-en-1-yl substituents at positions 4 and 6 as well as a 3-methylbutanoyl group at the 2-position. It has a role as an antibacterial drug, an antioxidant, a cyclooxygenase 2 inhibitor and a metabolite. It is a diketone, a triol, a cyclic ketone, an aromatic ketone and a tertiary alpha-hydroxy ketone. | [Synthesis]
The 700g crushed hops are loaded into the extractor, and suitable extraction pressure, extraction temperature, CO2 flow rate and extraction time are selected. CO2 enters into the extractor through cooling and pressurization, and in the heated and pressuri | [in vivo]
Humulone (10 or 20 mg/kg; IP; single dose) shortens sleep onset and increases the duration of sleep induced by pentobarbital and decreases the spontaneous locomotion in open field at 20 mg/kg[2].
Humulone (10 μmol; applied topically to the dorsal shaved area) pre-treatment significantly inhibited TPA (10 nmol)-induced COX-2 expression in Female ICR mice (6-7 weeks of age) skin[3].
Humulone (1, 10 μmol; applied topical; pre-treatment 30 min) suppresses TPA-induced NF-κB DNA binding. Humulone attenuates TPA-stimulated nuclear translocation of p65 and p50 subunit proteins of NF-κB[3].
| Animal Model: | Male BALB/cAnNRj mice (9-11 weeks of age)[2] | | Dosage: | 10 or 20 mg/kg | | Administration: | IP; pre-treatment before sodium pentobarbital (35 mg/kg; i.p.) and ethanol (3.5 g/kg) | | Result: | Significantly decreased the latency and prolonged the duration of sleep induced by pentobarbital at 20 mg/kg dose. These effects were not observed at a lower dose of 10 mg/kg.
Showed no effect on the onset of sleep induced by ethanol, but significantly increased sleep duration dose-dependently.
|
| [target]
IL Receptor | AP-1 | COX | p65 | NF-kB | IkB | VEGFR | Antifection | IKK | [IC 50]
COX-2 | [storage]
Store at -20°C | [Purification Methods]
Crystallise humulon from Et2O. It dissolves slightly in hot H2O but precipitates on cooling. It has max () 237 (13,760) and 282 (8,330) in EtOH. [Wollmer Chem Ber 49 780 1916, Carson J Am Chem Soc 73 4652 1951, Beilstein 8 II 537, 8 III 4034, 8 IV 3410.] |
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