26472-41-3

Basic information

• Product Name: HUMULONE*
• Synonyms: (6R)-3,5,6-trihydroxy-2-isovaleryl-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dienone;α-bitter acid;Humulone, mixture of homologues;α-Bitter acid, α-Lupulic acid;(6R)-2-(3-Methylbutyryl)-3,5,6-trihydroxy-4,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadiene-1-one;(6R)-4,6-Diprenyl-3,5,6-trihydroxy-2-(1-oxo-3-methylbutyl)-2,4-cyclohexadiene-1-one;[R,(-)]-3,5,6-Trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one;[R,(-)]-Humulone
• CAS NO: 26472-41-3
• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.4599
• EINECS: 247-725-0
• Product Categories: Miscellaneous Natural Products
• Mol File: 26472-41-3.mol
• Article Data: 4

Chemical Properties

• Melting Point: 65-66.5℃
• Boiling Point: 414.06°C (rough estimate)
• Flash Point: 313.4°C
• Appearance: /
• Density: 1.157±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 1.95E-15mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• Storage Temp.: −20°C
• PKA: 4.50±1.00(Predicted)
• CAS DataBase Reference: HUMULONE*(CAS DataBase Reference)
• NIST Chemistry Reference: HUMULONE*(26472-41-3)
• EPA Substance Registry System: HUMULONE*(26472-41-3)

Safety Data

• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 26472-41-3(Hazardous Substances Data)

Usage

Uses

(R)-Humulone (CAS# 26471-41-3) can be used as a chemosensory receptor ligand.

Purification Methods

Crystallise humulon from Et2O. It dissolves slightly in hot H2O but precipitates on cooling. It has max () 237 (13,760) and 282 (8,330) in EtOH. [Wollmer Chem Ber 49 780 1916, Carson J Am Chem Soc 73 4652 1951, Beilstein 8 II 537, 8 III 4034, 8 IV 3410.]

InChI:InChI=1/C21H30O5/c1-12(2)7-8-15-18(23)17(16(22)11-14(5)6)20(25)21(26,19(15)24)10-9-13(3)4/h7,9,14,23-24,26H,8,10-11H2,1-6H3/t21-/m1/s1

Upstream product

• 125137-35-1 (+/-)-humulone 
• 4374-93-0 deoxyhumulone 

Downstream Products

• 56143-68-1 (3aS,5aR,8aR)-3a-Hydroxy-7-isopropenyl-6,6-dimethyl-2-(3-methyl-butyryl)-tetrahydro-cyclopenta[c]pentalene-1,3,4-trione 
• 81677-88-5 3,7-Dihydroxy-2,2-dimethyl-6-(3-methyl-butyryl)-7a-(4-methyl-pent-3-enoyl)-3,4,4a,7a-tetrahydro-2H-cyclopenta[b]pyran-5-one 
• 504-85-8 4-methyl-pent-3-enoic acid 
• 78-84-2 isobutyraldehyde 
• 67-64-1 acetone 
• 78-78-4 methylbutane 
• 107152-23-8 3-methyl-1-(2,3,4,6-tetrahydroxy-5-isopentyl-phenyl)-butan-1-one 
• 1534-03-8 trans-isohumulone 
• 467-72-1 trans-isohumulone 
• 1594-20-3 dehydrohumulinic acid 
• 92051-58-6 5,8-Dihydroxy-2,2-dimethyl-8-(3-methyl-but-2-enyl)-6-(3-methyl-butyryl)-2,3,4,8-tetrahydro-chromen-7-one 
• 92051-62-2 8,10-Dihydroxy-2,2-dimethyl-9-(3-methyl-but-2-enyl)-7-(3-methyl-butyryl)-1-oxa-spiro[4.5]deca-7,9-dien-6-one 
• 92051-59-7 6,7-Dihydroxy-2,2-dimethyl-6-(3-methyl-but-2-enyl)-8-(3-methyl-butyryl)-2,3,4,6-tetrahydro-chromen-5-one 
• 24183-31-1 (+/-)-3,4r-dihydroxy-2-isovaleryl-5t-(3-methyl-but-2-enyl)-cyclopent-2-enone 

Relevant articles and documents

Conversion of deoxyhumulone into the HOP α-acid humulone

In the final step of the biosynthesis of hop bitter acids an oxidation leads to the formation of α-acids. A method was set up to analyse the bitter acids in the presence of proteins, since proteins from a crude hop extract were found to interact with the

Method of acylation of phloroglucinol

A method of acylation of phloroglucinol in the presence of a Friedel Crafts catalyst which is effected in the presence of nitromethane and dichloromethane so as to produce an acylphloroglucinol. The acylphloroglucinol is reacted with a compound selected f