25522-96-7

Basic information

• Product Name: 3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-one
• Synonyms: 3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-one;2-(1-Oxo-3-methylbutyl)-3,4-dihydroxy-4-(1-oxo-4-methyl-3-pentenyl)-5-prenyl-2-cyclopentene-1-one;2-(3-Methylbutanoyl)-3,4-dihydroxy-4-(4-methyl-3-pentenoyl)-5-(3-methyl-2-butenyl)-2-cyclopentene-1-one;2-(3-Methylbutyryl)-3,4-dihydroxy-5-(3-methyl-2-butenyl)-4-(4-methyl-3-pentenoyl)-2-cyclopentene-1-one;3,4-Dihydroxy-5-(3-methyl-2-butenyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-pentenyl)-2-cyclopenten-1-one;Einecs 247-072-1;3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
• CAS NO: 25522-96-7
• Molecular Formula: C₂₁H₃₀O₅
• Molecular Weight: 362.4599
• EINECS: 247-072-1
• Mol File: 25522-96-7.mol

Chemical Properties

• Melting Point: -10--5 °C
• Boiling Point: 530.5°C at 760 mmHg
• Flash Point: 288.7°C
• Appearance: /
• Density: 1.135g/cm³
• Vapor Pressure: 1.81E-13mmHg at 25°C
• Refractive Index: 1.536
• PKA: 2.87±0.58(Predicted)
• CAS DataBase Reference: 3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-one(25522-96-7)
• EPA Substance Registry System: 3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-one(25522-96-7)

Safety Data

• Hazardous Substances Data: 25522-96-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-one is used as a pharmaceutical compound for its potential therapeutic effects. The compound's unique structure allows it to interact with various biological targets, making it a promising candidate for the development of new drugs and treatments.
Used in Cosmetics Industry:
In the cosmetics industry, 3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-one is used as an active ingredient for its potential benefits in skincare and hair care products. Its chemical properties may contribute to improved skin hydration, anti-aging effects, and hair conditioning.
Used in Flavor and Fragrance Industry:
3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-one is used as a flavor and fragrance compound due to its unique aroma and taste profile. It can be employed in the creation of various scent formulations and flavor enhancers for the food and beverage industry.
Used in Brewing Industry:
In the brewing industry, 3,4-dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-one is used as a key component contributing to the bitter taste of beer. It is produced during the brewing process through thermal isomerism, which converts humulones to isohumulones, resulting in the characteristic bitter flavor of certain beer types.

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

Upstream product

• 26472-41-3 humulone 
• 467-72-1 trans-isohumulone 

Downstream Products

• 1594-20-3 dehydrohumulinic acid 
• 467-72-1 cis-isohumulone 

Relevant articles and documents

The Photolysis of trans-Isohumulone to Dehydrohumulinic Acid, a Key Route to the Development of Sunstruck Flavour in Beer

trans-Isohumulone (2) is photolysed to dehydrohumulonic acid (5) by a Norrish type 1 cleavage, affording a precursor of 3-methylbut-2-ene-1-thiol, the compound responsible for the sunstruck flavour of beer.

BICYCLIC ISOMERIZATION PRODUCTS OF HUMULONE

The humulone isomerization mixture is investigated by means of efficient preparative High Performance Liquid Chromatography.New bicyclic humulone isomers are isolated and identified (8 and 10 in fig.1).

Method of isomerizing humulone to isohumulone by catalytic acceleration with metal salts

The isomerization of humulone or a humulone-containing material is carried out by isomerization at elevated temperature and a pH below 9 in a liquid medium containing at least one salt of a bi-valent metal or of cerium.

Hop extract process and product

Hop extract in, e.g., hexane, pre-isomerized, optionally pre-reduced, is extracted with aqueous KOH to give potassium isohumulate of 80%+ and preferably 90%+ purity. The hexane phase containing the remainder of the isohumulones is stripped of solvent and is suitable for kettle addition. In order to prevent foaming during subsequent concentration, the aqueous extract containing about 6% solids is acidified to a pH less than the pKa of isohumulone and is concentrated under reduced pressure. After concentration, the material is treated with KOH to form the water soluble isohumulone salt which is added to beer post-kettle. At a critical optimum pH range, dependent upon the ratio of water to hexane phase used in the initial extraction, from 0.1 to 0.75 of the isohumulones may be extracted in the highly purified form. A generalized technique for establishing conditions that will give such desired fractions and residues is disclosed.