Lupulone

Names

[ CAS No. ]:
468-28-0

[ Name ]:
Lupulone

[Synonym ]:
2,4-Cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-
β-Lupulic acid
B'-Acid
EINECS 207-405-3
3,5-Dihydroxy-4-(3-methylbutanoyl)-2,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
β-Bitter acid
b-Lupulic Acid
3,5-Dihydroxy-4-(3-methylbutanoyl)-2,6,6-tris(3-methyl-2-buten-1-yl)-2,4-cyclohexadien-1-one
b-Bitter Acid
Lupulon
Lupulone
2,4-Cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(3-methyl-1-oxobutyl)-

Biological Activity

[Description]:

Lupulone is a beta-acid from the hop plant H. lupulus with diverse biological activities including antibacterial, antioxidant, and anticarcinogenic properties[1][2][3].

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Bacterial

[References]

[1]. Tagashira M, et al. Antioxidative activity of hop bitter acids and their analogues. Biosci Biotechnol Biochem. 1995 Apr;59(4):740-2.

[2]. Lamy V, et al. Lupulone, a hop bitter acid, activates different death pathways involving apoptotic TRAIL-receptors, in human colon tumor cells and in their derived metastatic cells. Apoptosis 13(10), 1232-1242 (2008).

[3]. Bocquet L, et al. Phenolic Compounds from Humulus lupulus as Natural Antimicrobial Products: New Weapons in the Fight against Methicillin Resistant Staphylococcus aureus, Leishmania mexicana and Trypanosoma brucei Strains. Molecules. 2019 Mar 14;24(6):1024.

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
498.4±45.0 °C at 760 mmHg

[ Melting Point ]:
93ºC

[ Molecular Formula ]:
C₂₆H₃₈O₄

[ Molecular Weight ]:
414.58

[ Flash Point ]:
269.3±25.2 °C

[ Exact Mass ]:
414.277008

[ PSA ]:
74.60000

[ LogP ]:
8.77

[ Vapour Pressure ]:
0.0±2.9 mmHg at 25°C

[ Index of Refraction ]:
1.530

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: OK5950000

CHEMICAL NAME :: Lupulone

CAS REGISTRY NUMBER :: 468-28-0

LAST UPDATED :: 199309

DATA ITEMS CITED :: 7

MOLECULAR FORMULA :: C26-H38-O4

MOLECULAR WEIGHT :: 414.64

WISWESSER LINE NOTATION :: L6V BHJ B2UY1&1 B2UY1&1 CQ DV1Y1&1 EQ F2UY1&1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 100 mg/kg

TOXIC EFFECTS :: Behavioral - ataxia Lungs, Thorax, or Respiration - cyanosis

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 17,79,1967

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 330 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 8,281,1949

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 525 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - excitement Lungs, Thorax, or Respiration - other changes

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 17,79,1967

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 600 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: 85GDA2 "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980- Volume(issue)/page/year: 8(2),39,1982

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 600 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 8,281,1949

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 82,1,1950

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 130 mg/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold

REFERENCE :: FEPRA7 Federation Proceedings, Federation of American Societies for Experimental Biology. (Bethesda, MD) V.1-46, 1942-87. Volume(issue)/page/year: 8,281,1949

Safety Information

[ Hazard Codes ]:
T: Toxic;

[ Risk Phrases ]:
R25

[ RIDADR ]:
UN 2811

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)