Humulone

Base Information

• Chemical Name: Humulone
• CAS No.: 26472-41-3
• Molecular Formula: C21H30 O5
• Molecular Weight: 362.466
• European Community (EC) Number: 247-725-0
• DSSTox Substance ID: DTXSID501019081
• Nikkaji Number: J122.043H,J728.155B
• Wikipedia: Humulone
• Wikidata: Q419456
• Metabolomics Workbench ID: 53217
• ChEMBL ID: CHEMBL3814665,CHEMBL1592914
• Mol file: 26472-41-3.mol

Synonyms:3,5,6-trihydroxy-4-isovaleryl-2,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadiene-1-one;alpha bitter acid;humulon;humulone

Chemical Property of Humulone

Chemical Property:

• Vapor Pressure: 1.95E-15mmHg at 25°C
• Melting Point: 65-66.5℃
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 571.4°Cat760mmHg
• PKA: 4.50±1.00(Predicted)
• Flash Point: 313.4°C
• PSA: 94.83000
• Density: 1.157g/cm³
• LogP: 4.25220
• Storage Temp.: −20°C
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 362.20932405
• Heavy Atom Count: 26
• Complexity: 711

Purity/Quality:

99% ^*data from raw suppliers

Humulone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)O)O)CC=C(C)C)O
• Isomeric SMILES: CC(C)CC(=O)C1=C(C(=C([C@@](C1=O)(CC=C(C)C)O)O)CC=C(C)C)O
• Uses: (R)-Humulone (CAS# 26471-41-3) can be used as a chemosensory receptor ligand.

Technology Process of Humulone

There total 4 articles about Humulone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 50.0%

→ humulone (26472-41-3)

Guidance literature:

Reference yield:

deoxyhumulone (4374-93-0) → humulone (26472-41-3)

Guidance literature:

With gland protein extracts from the young cones of the hop cultivars 'Brewer's Gold'; In methanol; water; at 30 ℃; for 0.333333h;

DOI:10.1016/S0031-9422(96)00671-1

Reference yield:

(6S)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one → humulone (26472-41-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 125 - 145 °C / Inert atmosphere; Sealed tube

2: trans-4-cyclohexene-1,2-diamine / isopropyl alcohol / Resolution of racemate

With trans-4-cyclohexene-1,2-diamine; In isopropyl alcohol;

upstream raw materials:

deoxyhumulone

(+/-)-humulone

Downstream raw materials:

(+/-)-3,4r-dihydroxy-2-isovaleryl-5t-(3-methyl-but-2-enyl)-cyclopent-2-enone

trans-isohumulone

trans-isohumulone

dehydrohumulinic acid

Refernces

The photochemistry of trans-isohumulone, a bitter flavouring component of beer

10.1139/V08-072

The study focuses on the photochemistry of trans-isohumulone, a key bitter flavoring component in beer, to understand its degradation under UV light, which is crucial for the brewing industry. The researchers irradiated methanolic solutions of trans-isohumulone with UV light at 313 nm, yielding four primary products containing an enolized cyclic β-triketone moiety: cis-isohumulone, humulone, dehydro-isohumulone, and dehydro-humulinic acid. Nine volatile products derived from the side chain of trans-isohumulone were also identified and quantified. The study aimed to clarify previous contradictory reports on the photolysis products of isohumulone and to provide insights into the unexpected photochemistry of alkenyl-substituted enolized cyclic β-triketones. The chemicals used in the study served as solvents, reagents for the irradiation process, and standards for the identification and quantification of the photoproducts.