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ChemicalBook--->CAS DataBase List--->468-28-0

468-28-0

468-28-0 Structure

468-28-0 Structure
IdentificationBack Directory
[Name]

LUPULONE
[CAS]

468-28-0
[Synonyms]

lupulon
LUPULONE
b’’-acid
B-LUPULIC ACID
lohexadien-1-one
BETA-BITTER ACID
BETA-LUPULIC ACID
Lupulone beta-acid
1-Amino-8-naphthol-3,5-disulfonic acid
5-Amino-4-hydroxy-1,7-naphthalenedisulfonic acid
3,5-DIHYDROXY-2-(3-METHYLBUTANOYL)-4,6,6-TRIS(3-METHYLBUT-2-ENYL)CYCLOHE
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
3,5-dihydroxy-2-isovaleryl-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
3,5-DIHYDROXY-2,6,6-TRIS(3-METHYL-2-BUTENYL)-4-(3-METHYLBUTYRYL)-2,4-CYCLOHEXADIENONE
3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
3,5-Dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
3,5-dihydroxy-2,6,6-tris(3-methylbut-2-enyl)-4-(3-methyl-1-oxobutyl)cyclohexa-2,4-dien-1-one
3,5-dihydroxy-2,6,6-tris(3-methylbuten-2-yl)-4-(3-methyl-1-oxobutyl)cyclohexa-2,4-dien-1-one
2,4-Cyclohexadien-1-one,3,5-dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(3-methyl-1-oxobutyl)-
β-Bitter acid, β-Lupulic acid, 3,5-Dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methylbutyryl)-2,4-cyclohexadienone
[EINECS(EC#)]

207-405-3
[Molecular Formula]

C26H38O4
[MDL Number]

MFCD00075970
[MOL File]

468-28-0.mol
[Molecular Weight]

414.58
Chemical PropertiesBack Directory
[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℃
Safety DataBack Directory
[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)
Hazard InformationBack Directory
[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.]
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