 Chemical Structure.png)
Physicochemical Properties
| Molecular Formula | C21H30O5 |
| Molecular Weight | 362.46 |
| Exact Mass | 362.209 |
| CAS # | 26472-41-3 |
| PubChem CID | 442911 |
| Appearance | Light yellow to yellow ointment |
| Density | 1.2±0.1 g/cm3 |
| Boiling Point | 571.4±50.0 °C at 760 mmHg |
| Melting Point | 65-66.5℃ |
| Flash Point | 313.4±26.6 °C |
| Vapour Pressure | 0.0±3.6 mmHg at 25°C |
| Index of Refraction | 1.558 |
| LogP | 5.14 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 7 |
| Heavy Atom Count | 26 |
| Complexity | 711 |
| Defined Atom Stereocenter Count | 1 |
| SMILES | CC(=CCC1=C([C@](CC=C(C)C)(C(=O)C(=C1O)C(=O)CC(C)C)O)O)C |
| InChi Key | VMSLCPKYRPDHLN-OAQYLSRUSA-N |
| InChi Code | 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 |
| Chemical Name | (6R)-3,5,6-trihydroxy-2-(3-methylbutanoyl)-4,6-bis(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: This product requires protection from light (avoid light exposure) during transportation and storage. |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| Targets | COX-2 |
| ln Vitro | In MC3T3-E1 cells, humulone (0.1, 1, 10, 100, 1000, and 10,000 nM; for 12 hours) reduces the quantity of produced PGE2 with a dose-dependent manner, with an IC50 of roughly 30 nM. The TNFK-treated cells' cyclooxygenase activity is decreased by humulone[1]. For a duration of 12 hours, humulone (0.1–10,000 nM) inhibits the rise in cyclooxygenase-2 mRNA that is caused by TNFα[1]. In MC3T3-E1 cells, humulone suppresses cyclooxygenase-2 activity with an IC50 of around 1.6 μM, but it barely impacts cyclooxygenase-1 activity below 10 μM[1]. |
| ln Vivo | At 10 or 20 mg/kg (IP; single dose), humulone reduces spontaneous movement in an open field and lengthens the time that pentobarbital-induced sleep lasts[2]. TPA (10 nmol)-induced COX-2 expression in the skin of female ICR mice (6-7 weeks old) was considerably reduced by humulone (10 μmol) administered topically to the dorsal shaved area prior to treatment[3]. Humulone (1, 10 μmol; topical; 30 min before to treatment) inhibits the NF-κB DNA binding that is triggered by TPA. The nuclear translocation of NF-κB's p65 and p50 subunit proteins is attenuated by humulone in response to TPA stimulation[3]. |
| Animal Protocol |
Animal/Disease Models: Male BALB/cAnNRj mice (9-11 weeks of age)[2] Doses: 10 or 20 mg/kg Route of Administration: IP; pre-treatment before sodium pentobarbital (35 mg/kg; ip) and ethanol (3.5 g/kg) Experimental Results: Dramatically diminished 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. demonstrated no effect on the onset of sleep induced by ethanol, but Dramatically increased sleep duration dose-dependently. |
| References |
[1]. Suppression of cyclooxygenase-2 gene transcription by humulon of beer hop extract studied with reference to glucocorticoid. FEBS Lett. 2000 Jan 14;465(2-3):103-6. [2]. Humulone Modulation of GABA A Receptors and Its Role in Hops Sleep-Promoting Activity. Front Neurosci. 2020 Oct 14;14:594708. [3]. Humulone inhibits phorbol ester-induced COX-2 expression in mouse skin by blocking activation of NF-kappaB and AP-1: IkappaB kinase and c-Jun-N-terminal kinase as respective potential upstream targets. Carcinogenesis. 2007 Jul;28(7):. |
| Additional Infomation |
Humulone is an optically active cyclic ketone consisting of 3,5,6-trihydroxycyclohexa-2,4-dien-1-one bearing two 3-methylbut-2-en-1-yl substituents at positions 4 and 6 as well as a 3-methylbutanoyl group at the 2-position. It has a role as an antibacterial drug, an antioxidant, a cyclooxygenase 2 inhibitor and a metabolite. It is a diketone, a triol, a cyclic ketone, an aromatic ketone and a tertiary alpha-hydroxy ketone. Humulon has been reported in Humulus lupulus with data available. |
Solubility Data
| Solubility (In Vitro) | DMSO : 50 mg/mL (137.95 mM) |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.7589 mL | 13.7946 mL | 27.5893 mL | |
| 5 mM | 0.5518 mL | 2.7589 mL | 5.5179 mL | |
| 10 mM | 0.2759 mL | 1.3795 mL | 2.7589 mL |