Lupulone

Modify Date: 2024-01-09 11:33:46

Lupulone structure	Common Name	Lupulone
	CAS Number	468-28-0	Molecular Weight	414.58
	Density	1.0±0.1 g/cm3	Boiling Point	498.4±45.0 °C at 760 mmHg
	Molecular Formula	C₂₆H₃₈O₄	Melting Point	93ºC
	MSDS	N/A	Flash Point	269.3±25.2 °C

Use of Lupulone

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

Name	3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
Synonym	More Synonyms

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.

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.

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

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

Hazard Codes	T: Toxic;
Risk Phrases	R25
RIDADR	UN 2811
Packaging Group	III
Hazard Class	6.1(b)

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)-

Shanghai Jizhi Biochemical Technology Co., Ltd
China
Product Name: Lupulone
Price: ￥1768.0/20mg
Purity: 98.0%
Stocking Period: 2 Day
Contact: Liu jia

DC Chemicals Limited
China
Product Name: Lupulon
Price: $Inquiry/100mg $Inquiry/250mg $Inquiry/500mg
Purity: 98.0%
Stocking Period: 3 Day
Contact: Tony Cao

Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: 3,5-dihydroxy-2,6,6-tris(3-methylbuten-2-yl)-4-(3-methyl-1-oxobutyl)cyclohexa-2,4-dien-1-one
Price: $Inquiry/100g $Inquiry/1kg $Inquiry/100kg $Inquiry/1000kg
Purity: 98.0%
Stocking Period: Inquiry
Contact: Ms Wang

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