| 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. | [target]
IL Receptor | AP-1 | COX | p65 | NF-kB | IkB | VEGFR | Antifection | IKK | [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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