Basic information
- CAS
25522-96-7- Standard SMILES
CC(C)=CCC(=O)C1(O)C(O)=C(C(=O)CC(C)C)C(=O)C1CC=C(C)C- InChIKey
QARXXMMQVDCYGZ-UHFFFAOYSA-N- Molecular formula
- C21H30O5
- Average molar mass
- 362.5 g/mol
- Monoisotopic mass
- 362.20932405
Overview
Isohumulone A is a monoterpenoid.
Names & identifiers
- Preferred name
- Isohumulone
- IUPAC
- 3,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one
- English 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
- Molecular formula
- C21H30O5
- Molecular weight
- 362.46
Names & synonyms
Isohumulone25522-96-73,4-dihydroxy-2-(3-methylbutanoyl)-5-(3-methylbut-2-enyl)-4-(4-methylpent-3-enoyl)cyclopent-2-en-1-one3,4-Dihydroxy-5-(3-methylbut-2-enyl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxopent-3-enyl)cyclopent-2-en-1-oneE2S413495YRefChem:1494272-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)-247-072-13,4-Dihydroxy-2-(3-methylbutanoyl)-5-(3-methyl-2-butenyl)-4-(4-methyl-3-pentenoyl)-2-cyclopenten-1-oneIsohumulone AUNII-E2S413495Y3,4-Dihydroxy-5-(3-methyl-2-buten-1-yl)-2-(3-methyl-1-oxobutyl)-4-(4-methyl-1-oxo-3-penten-1-yl)-2-cyclopenten-1-one; Iso-n-humulone; IsoHopCO2N
Show more names
30% Iso-alpha-acids Hop Extracts2-(1-Oxo-3-methylbutyl)-3,4-dihydroxy-4-(1-oxo-4-methyl-3-pentenyl)-5-prenyl-2-cyclopentene-1-one2-(3-Methylbutyryl)-3,4-dihydroxy-5-(3-methyl-2-butenyl)-4-(4-methyl-3-pentenoyl)-2-cyclopentene-1-one2-(3-Methylbutanoyl)-3,4-dihydroxy-4-(4-methyl-3-pentenoyl)-5-(3-methyl-2-butenyl)-2-cyclopentene-1-one
Properties
Computed structural properties
- XLogP
- 3.8
- Topological polar surface area
- 91.7 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 8
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 685
Experimental & physicochemical properties
Melting Point62 - 63 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- -10 · -10--5 °C
- Boiling point
- 530.5 · 530.5±50.0 °C(Predicted)
- Density
- 1.135 · 1.135±0.06 g/cm3(Predicted)
- solubility
- Dichloromethane (Slightly), Methanol (Slightly)
- form
- Solid
- pka
- 2.87 · 2.87±0.58(Predicted)
- color
- Yellow
- LogP
- 6.029 · 6.029 (est)
- FDA UNII
- 2 S413495Y · E2S413495Y
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Chemistry & industry
Pharmacology
Cellular LocationsCytoplasm
Applications
UsesIsohumulone is a chemical compound that contributes to the bitter taste of beer. It belongs to a class of compound known as the Iso-alpha acids found in the hops.
Suppliers5 total
BOC Sciences[email protected]
BOC Sciences+1-631-485-4226 · [email protected]
DAYANG CHEM (HANGZHOU) CO.,LTD+86-88938639 +86-17705817739 · [email protected]
TopScience Biochemical00852-68527855 · [email protected]
Wuhan Fortuna Chemical Co., Ltd+86-27-59207850 · [email protected]
Additional notes
DefinitionChEBI: A cyclic ketone that is the naturally occurring (4S,5R) enantiomer of the cis-isomer of isohumolone, produced during the brewing process due to thermal isomerism, which converts humulones to isohumulones v a an acyloin-type ring contraction.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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