CIS-ISOHUMULONE

Base Information

• Chemical Name: CIS-ISOHUMULONE
• CAS No.: 1534-03-8
• Molecular Formula: C21H30O5
• Molecular Weight: 362.466
• Mol file: 1534-03-8.mol

Synonyms:Isohumulon-A;(4R,5S)-3,4-Dihydroxy-5-(3-methyl-but-2-enyl)-2-(3-methyl-butyryl)-4-(4-methyl-pent-3-enoyl)-cyclopent-2-enone;(-)-cis-isohumulone;isohumulone;cis-Isohumulon;(4R)-3,4r-dihydroxy-2-isovaleryl-5c-(3-methyl-but-2-enyl)-4-(4-methyl-pent-3-enoyl)-cyclopent-2-enone;(4R)-3,4r-Dihydroxy-2-isovaleryl-5c-(3-methyl-but-2-enyl)-4-(4-methyl-pent-3-enoyl)-cyclopent-2-enon;

Chemical Property of CIS-ISOHUMULONE

Chemical Property:

• Boiling Point: 530.5±50.0 °C
• PSA: 91.67000
• LogP: 3.62540

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Isohumulone A1 can be used as a polysaccharide thickener compound to form and improve the quality of foams for beverages. It can also be used for cancer treatment.

Technology Process of CIS-ISOHUMULONE

There total 9 articles about CIS-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: 50.0%

trans-isohumulone (467-72-1) → humulone + dehydro-humulinic acid (1059453-46-1) + dehydro-isohumulone (1059453-44-9) + trans-isohumulone (1534-03-8)

Guidance literature:

In methanol; Further byproducts.; UV-irradiation;

DOI:10.1139/V08-072

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;

upstream raw materials:

humulone

trans-isohumulone

trans-isohumulone

Downstream raw materials:

dehydrohumulinic acid

cis-isohumulone

(R)-cis-rho-isohumulone

(S)-cis-rho-isohumulone

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.