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)

color 

White to off-white

Water Solubility 

1g/L at 20℃

Stability:

Hygroscopic

Major Application

food and beverages
pharmaceutical

LogP

4.5 at 20℃

Safety Information

Hazard Codes 

T

Risk Statements 

25

Safety Statements 

45

RIDADR 

2811

WGK Germany 

WGK 3

RTECS 

OK5950000

HazardClass 

6.1(b)

PackingGroup 

III

Storage Class

11 - Combustible Solids

Toxicity

LD50 in mice, rats (mg/kg): 525, 100 orally (Hnsel, Wagener)

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-).

Synthesis

The process for the extraction and isolation of Lupulone from hops is as follows: Step a, the hops compression is loaded into a subcritical ultrasonic extractor, the appropriate temperature and pressure are selected, the R134a mixed solvent is passed into the extractor, the active ingredients in the extracted substance are dissolved in the liquid or subcritical state of the R134a mixed solvent, and the resulting extract is filtered through the filter, and the filtrate is pumped into the separator. Step b, the temperature and pressure are adjusted so that the R134a in the R134a mixed solvent is converted from liquid state to gas state and separated from the extract, and the extract containing methanol is concentrated by the concentrating evaporator to obtain the hop extract, which enters into the analyzing crystallization section. The solvent (R134a, methanol) obtained from evaporation is recovered by condensation system and returned to the extraction device for recycling. Step c, take a certain amount of hop extract in a reactor, add water according to the weight ratio of hop extract:water=1:2, adjust the pH to 8.5-9.0 with 10% NaOH at a temperature of 45??-50??, stir for 30min, and let it stand at room temperature for 6h, extract and filter, and collect insoluble matter. Step d, the insoluble material was added to water at the weight ratio of insoluble material:water = 1:10, and the pH was adjusted to 12.5 to 13.0 with 10% NaOH at 45??C to 50??C, stirred for 30 min, and allowed to stand for 6h at room temperature, and filtered. Step e, the filtrate with dilute phosphoric acid to adjust the pH value to 8.5, stirring for 30min, filtration, the collection of insoluble material, that is, to obtain the crude serpentine ketone; hexane on the serpentine ketone crude recrystallization of the white needle state Lupulone.

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.]

LUPULONE(468-28-0)Related Product Information

• HUMULONE
• MOSLOFLAVONE
• Artemether
• beta-Sitosterol
• Cnidii Fructus
• METHYL CYCLOHEXADIENE
• 2,7-dimethyl-2,6-octadiene
• 6-Methyl-5-hepten-2-one
• 1,3-CYCLOHEXADIENE
• LUPULONE(P)
• 1,3,5,5-TETRAMETHYL-1,3-CYCLOHEXADIENE
• 2,5-DIMETHYL-2-OCTEN-6-ONE
• LUPULONE
• 2,7-dimethyloct-5-en-4-one
• 1-METHYL-1,3-CYCLOHEXADIENE
• 2-(3-ALLYL)-4-PENTEN-1-OL
• 2,4-DIMETHYL-2,6-HEPTADIENAL
• 2,2,4-TRIMETHYL-3-HEXENE