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ChemicalBook--->CAS DataBase List--->26472-41-3

26472-41-3

26472-41-3 Structure

26472-41-3 Structure
IdentificationBack 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 PropertiesBack 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
Safety DataBack Directory
[WGK Germany ]

3
[F ]

10-23
Hazard InformationBack 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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