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HUMULONE

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HUMULONE Basic information

Product Name:
HUMULONE
Synonyms:
  • (6S)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
  • (6R)-3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienone
  • α-bitter acid
  • Humulone, mixture of homologues
  • α-Bitter acid, α-Lupulic acid
  • (6R)-2-(3-Methylbutyryl)-3,5,6-trihydroxy-4,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadiene-1-one
  • (6R)-4,6-Diprenyl-3,5,6-trihydroxy-2-(1-oxo-3-methylbutyl)-2,4-cyclohexadiene-1-one
  • [R,(-)]-3,5,6-Trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
CAS:
26472-41-3
MF:
C21H30O5
MW:
362.46
EINECS:
247-725-0
Product Categories:
  • Miscellaneous Natural Products
Mol File:
26472-41-3.mol
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HUMULONE Chemical Properties

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)
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Safety Information

WGK Germany 
3
10-23
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HUMULONE Usage And Synthesis

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

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.]

HUMULONESupplier

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