trans-Isohumulone

Base Information

• Chemical Name: trans-Isohumulone
• CAS No.: 467-72-1
• Molecular Formula: C21H30O5
• Molecular Weight: 362.466
• UNII: MH0ZZC7U5J
• DSSTox Substance ID: DTXSID601316206
• Nikkaji Number: J258.535I
• Wikidata: Q27284022
• Mol file: 467-72-1.mol

Synonyms:trans-Isohumulone;Photoisohumulone;Isohumulone A2;(-)-trans-Isohumulone;MH0ZZC7U5J;467-72-1;Isohumulone, trans-(-)-;Isohumulone A;2-Cyclopenten-1-one, 3,4-dihydroxy-5-(3-methyl-2-buten-1-yl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-penten-1-yl)-, (4S,5S)-;2-Cyclopenten-1-one, 3,4-dihydroxy-5-(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-pentenyl)-, (4S,5S)-;2-Cyclopenten-1-one, 3,4-dihydroxy-5-(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-pentenyl)-, (4S-trans)-;3-Penten-1-one, 1-(1,2-dihydroxy-3-isovaleryl-5-(3-methyl-2-butenyl)-4-oxo-2-cyclopenten-1-yl)-4-methyl-, cis-(-)-;trans-(-)-isohumulone;UNII-MH0ZZC7U5J;SCHEMBL820446;DTXSID601316206;Q27284022

Chemical Property of trans-Isohumulone

Chemical Property:

• PSA: 91.67000
• LogP: 3.62540
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 362.20932405
• Heavy Atom Count: 26
• Complexity: 685

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC(=O)C1=C(C(C(C1=O)CC=C(C)C)(C(=O)CC=C(C)C)O)O
• Isomeric SMILES: CC(C)CC(=O)C1=C([C@@]([C@@H](C1=O)CC=C(C)C)(C(=O)CC=C(C)C)O)O
• General Description: **Conclusion:** TRANS-ISOHUMULONE is a bitter flavouring compound found in beer, known for its susceptibility to photodegradation under UV light, leading to the formation of various photoproducts such as cis-isohumulone, humulone, and dehydro derivatives. Its photochemical behavior highlights its instability and the potential impact on beer flavor when exposed to light.

Technology Process of trans-Isohumulone

There total 5 articles about trans-Isohumulone 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: 62.0%

trans-isohumulone (467-72-1,1534-03-8,25522-96-7,29788-65-6,35928-10-0,35928-11-1,38574-02-6,88035-12-5) → dehydrohumulinic acid (1594-20-3) + cis-isohumulone (467-72-1,1534-03-8,25522-96-7,29788-65-6,35928-10-0,35928-11-1,38574-02-6,88035-12-5)

Guidance literature:

In methanol; for 3.5h; Irradiation;

Reference yield:

humulone (26472-41-3) → trans-isohumulone (1534-03-8) + trans-isohumulone (467-72-1,1534-03-8,25522-96-7,29788-65-6,35928-10-0,35928-11-1,38574-02-6,88035-12-5) + dehydrohumulinic acid (1594-20-3) + 5,8-Dihydroxy-2,2-dimethyl-8-(3-methyl-but-2-enyl)-6-(3-methyl-butyryl)-2,3,4,8-tetrahydro-chromen-7-one (92051-58-6)

Guidance literature:

With disodium hydrogenphosphate; citric acid; In water; for 2.5h; Further byproducts given. Yields of byproduct given; Heating; pH 5.4;

Reference yield:

humulone (26472-41-3) → trans-isohumulone (1534-03-8) + trans-isohumulone (467-72-1,1534-03-8,25522-96-7,29788-65-6,35928-10-0,35928-11-1,38574-02-6,88035-12-5) + dehydrohumulinic acid (1594-20-3) + 6,7-Dihydroxy-2,2-dimethyl-6-(3-methyl-but-2-enyl)-8-(3-methyl-butyryl)-2,3,4,6-tetrahydro-chromen-5-one (92051-59-7)

Guidance literature:

With disodium hydrogenphosphate; citric acid; In water; for 2.5h; Yield given. Further byproducts given. Yields of byproduct given; Heating; pH 5.4;

upstream raw materials:

trans-isohumulone

humulone

Downstream raw materials:

dehydro-humulinic acid

dehydro-isohumulone

trans-isohumulone

4-methyl-pent-3-enoic 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.

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