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Moligand™, ≥98% Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
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Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
In Vivo
Humulone (10 or 20 mg/kg; IP; single dose) shortens sleep onset and increases the duration of sleep induced by pentobarbital and decreases the spontaneous locomotion in open field at 20 mg/kg. Humulone (10 μmol; applied topically to the dorsal shaved area) pre-treatment significantly inhibited TPA (10 nmol)-induced COX-2 expression in Female ICR mice (6-7 weeks of age) skin. Humulone (1, 10 μmol; applied topical; pre-treatment 30 min) suppresses TPA-induced NF-κB DNA binding. Humulone attenuates TPA-stimulated nuclear translocation of p65 and p50 subunit proteins of NF-κB. MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Male BALB/cAnNRj mice (9-11 weeks of age)Dosage: 10 or 20 mg/kg Administration: IP; pre-treatment before sodium pentobarbital (35 mg/kg; i.p.) and ethanol (3.5 g/kg) Result: Significantly decreased the latency and prolonged the duration of sleep induced by pentobarbital at 20 mg/kg dose. These effects were not observed at a lower dose of 10 mg/kg. Showed no effect on the onset of sleep induced by ethanol, but significantly increased sleep duration dose-dependently.
Form:Oil
| Canonical Smiles | CC(C)CC(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)O)O)CC=C(C)C)O |
|---|---|
| IUPAC Name | (6R)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one |
| InChIKey | VMSLCPKYRPDHLN-OAQYLSRUSA-N |
| INCHI | 1S/C21H30O5/c1-12(2)7-8-15-18(23)17(16(22)11-14(5)6)20(25)21(26,19(15)24)10-9-13(3)4/h7,9,14,23-24,26H,8,10-11H2,1-6H3/t21-/m1/s1 |
| Isomeric SMILES | CC(C)CC(=O)C1=C(C(=C([C@@](C1=O)(CC=C(C)C)O)O)CC=C(C)C)O |
| Alternate CAS | 26472-41-3 |
| PubChem CID | 442911 |
| MeSH Entry Terms | 3,5,6-trihydroxy-4-isovaleryl-2,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadiene-1-one;alpha bitter acid;humulon;humulone |
| Molecular Weight | 362.46 |
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organic oxygen compounds |
| Class | Organooxygen compounds |
| Subclass | Carbonyl compounds |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Acyloins |
| Alternative Parents | Vinylogous acids Tertiary alcohols Cyclic ketones Polyols Enols Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| Substituents | Acyloin - Vinylogous acid - Tertiary alcohol - Cyclic ketone - Ketone - Polyol - Enol - Organic oxide - Hydrocarbon derivative - Alcohol - Aliphatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as acyloins. These are organic compounds containing an alpha hydroxy ketone. Acyloins are formally derived from reductive coupling of carboxylic acyl groups. |
| External Descriptors | Phloroglucinols |
| Solubility | DMSO : 50 mg/mL (137.95 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 362.500 g/mol |
| XLogP3 | 4.200 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 7 |
| Exact Mass | 362.209 Da |
| Monoisotopic Mass | 362.209 Da |
| Topological Polar Surface Area | 94.800 Ų |
| Heavy Atom Count | 26 |
| Formal Charge | 0 |
| Complexity | 711.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 1 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
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