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:

4-methyl-pent-3-enoic acid

isobutyraldehyde

acetone

(3aS,5aR,8aR)-3a-Hydroxy-7-isopropenyl-6,6-dimethyl-2-(3-methyl-butyryl)-tetrahydro-cyclopenta[c]pentalene-1,3,4-trione

Refernces

• 1、 -. "CIS 3,4-DIHYDROXY-2-(3-METHYLBUTANOYL)-5-(3-METHYLBUTYL)-4-(4-METHYLPENTANOYL)CYCLOPENT-2-EN-1-ONE DERIVATIVES, SUBSTANTIALLY ENANTIOMERICALLY PURE COMPOSITIONS AND METHODS". Page/Page column 16. . Retrieved 2012/05/07.
• 2、 -. "Hydroperoxy-desoxyhumulones". . . Retrieved 2008/06/13.