Basic information Safety Supplier Related

LUPULONE

Basic information Safety Supplier Related

LUPULONE Basic information

Product Name:
LUPULONE
Synonyms:
  • 2,4-cyclohexadien-1-one,3,5-dihydroxy-4-isovaleryl-2,6,6-tris(3-methyl-2-but
  • 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-2,4-cyc
  • b’’-acid
  • lohexadien-1-one
  • lupulon
  • LUPULONE
  • B-LUPULIC ACID
  • BETA-LUPULIC ACID
CAS:
468-28-0
MF:
C26H38O4
MW:
414.58
EINECS:
207-405-3
Product Categories:
  • Hop Compounds
Mol File:
468-28-0.mol
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LUPULONE Chemical Properties

Melting point:
93℃
Boiling point:
453.43°C (rough estimate)
Density 
1.045±0.06 g/cm3 (20 ºC 760 Torr)
vapor pressure 
0Pa at 20℃
refractive index 
1.4840 (estimate)
storage temp. 
Store at -20°C
solubility 
Methanol: slightly soluble
form 
A solid
pka
4.50±1.00(Predicted)
Water Solubility 
1g/L at 20℃
Stability:
Hygroscopic
LogP
4.5 at 20℃
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Safety Information

Hazard Codes 
T
Risk Statements 
25
Safety Statements 
45
RIDADR 
2811
RTECS 
OK5950000
HazardClass 
6.1(b)
PackingGroup 
III
Toxicity
LD50 in mice, rats (mg/kg): 525, 100 orally (Hnsel, Wagener)
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LUPULONE Usage And Synthesis

Uses

Lupulone is a hop plant (Humulus lupulus L.) acid that inhibits tumorigenicity of hepatocellular carcinoma cells.

Definition

ChEBI: Lupulone is a beta-bitter acid in which the acyl group is specified as 3-methylbutanoyl. It has a role as an antimicrobial agent, an apoptosis inducer, an angiogenesis inhibitor and an antineoplastic agent. It is a conjugate acid of a lupulone(1-).

Purification Methods

Crystallise Lupulon from 90% MeOH, hexane or pet ether at low temperature. It has also been purified by chromatography through Kieselgel. [Wieland et al. Chem Ber 102 2012 1925, Riedl Chem Ber 85 692 1952, Beilstein 7 II 856, 7 III 4752, 7 IV 2866.]

LUPULONESupplier

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