| Size | Price | Stock | Qty |
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| 1mg |
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| 5mg |
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| 100mg | |||
| Other Sizes |
| ln Vitro |
8-Hydroxybergapten served as a substrate for O-methyltransferase present in crude, desalted cell extracts from Ruta graveolens cultures. In the presence of S-adenosylmethionine as the methyl donor, these extracts converted 8-Hydroxybergapten to isopimpinellin.[1]
A mixed substrate experiment suggested that the O-methylation of 8-Hydroxybergapten and 5-hydroxyxanthotoxin are catalyzed by different, specific enzymes.[1] |
|---|---|
| ln Vivo |
8-Hydroxy[Me-14C]bergapten was converted to isopimpinellin by Ruta graveolens culture cells with a high degree of incorporation, indicating it can function as a biosynthetic intermediate in vivo.[1]
Attempts to trap free or glucosidically bound 8-Hydroxybergapten in Ruta cell extracts after feeding with [2-14C]umbelliferone were unsuccessful, likely due to rapid metabolism upon entry into cells.[1] |
| Enzyme Assay |
O-Methyltransferase activity was assayed using crude, desalted extracts from Ruta graveolens culture cells (7-18 days old). The assay mixture typically contained cell extract, Tris-HCl buffer (pH 7.5), phenolic substrate (e.g., 8-Hydroxybergapten), S-[Me-14C]adenosylmethionine as the methyl donor, and MgCl₂. Incubation was carried out at 30°C for 1 hour. After incubation, carrier isopimpinellin was added, and the product was extracted with ether, purified by thin-layer chromatography (TLC), and analyzed by UV spectrometry and radioactivity measurement.[1]
For mixed substrate experiments to probe enzyme specificity, reactions were run with either 8-Hydroxybergapten or 5-hydroxyxanthotoxin alone, or with both substrates together, under conditions approaching substrate saturation. The reaction rates were compared to infer whether one or two distinct enzymes were involved.[1] |
| Cell Assay |
Ruta graveolens cells were cultured in shake flasks. For feeding experiments, filter-sterilized solutions of coumarin precursors (e.g., bergapten, xanthotoxin, or 8-Hydroxy[Me-14C]bergapten) were added to vigorously growing cultures.[1]
After the metabolic period, cells were extracted with ethanol. Coumarins were isolated through a series of steps including partition between methanol-water and hexane, continuous ether extraction, separation of phenolic and non-phenolic fractions, vacuum sublimation, and chromatography (column chromatography and/or TLC). Isopimpinellin was purified and identified by its fluorescence, UV spectrum, and melting point, and its radioactivity was measured.[1] Trapping experiments aimed at detecting intermediate 8-Hydroxybergapten involved analyzing the free phenolic fraction and the fraction hydrolyzable by β-glucosidase (emulsin) from cell extracts using TLC with authentic standards.[1] |
| Toxicity/Toxicokinetics |
Toxicity Summary
Many furanocoumarins act through mechanisms based on their ability to form photoadducts with DNA and other cellular components, such as RNA, proteins, and membrane proteins like phospholipases A2 and C, calcium-dependent and cAMP-dependent protein kinases, and epidermal growth factor. Furanocoumarins can intercalate between DNA base pairs and form cycloadducts upon UVA irradiation. (L579) |
| References | |
| Additional Infomation |
9-Hydroxy-4-methoxypsoralen is a type of psoralen compound. 8-Hydroxybergamot lactone has been found in Angelica sinensis, Resveratrol and other organisms with relevant data. 9-Hydroxy-4-methoxypsoralen is found in pome fruits. 9-Hydroxy-4-methoxypsoralen was isolated from Mexican apple (Casimiroa edulis). 8-Hydroxybergamot lactone (HB) is a phenolic furanocoumarin, specifically an 8-hydroxy derivative of bergamot lactone (5-methoxypsoralen). [1] It is considered a potential biosynthetic intermediate for the conversion of bergamot lactone to isopsoralen (5,8-dimethoxypsoralen), which is achieved through 8-hydroxylation and subsequent O-methylation. [1]
Studies have shown that the pathway via flavotoxin (8-methoxypsoralen) is the main pathway for isopsoralen biosynthesis, while the bergamot lactone/8-hydroxybergamot lactone pathway plays a relatively minor role. This may be because the activity of the putative 8-hydroxylase acting on bergamot lactone is lower than that acting on psoralen. 5-hydroxylase acts on flavotoxin. [1] The natural presence of free 8-hydroxybergamot lactone in plants has not been determined, and its reported isolation is likely artificial. [1] |
| Molecular Formula |
C12H8O5
|
|---|---|
| Molecular Weight |
232.1889
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| Exact Mass |
232.037
|
| CAS # |
1603-47-0
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| PubChem CID |
3083726
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| Appearance |
Light yellow to green yellow solid powder
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| Density |
1.5±0.1 g/cm3
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| Boiling Point |
488.2±45.0 °C at 760 mmHg
|
| Melting Point |
222.5 - 223 °C
|
| Flash Point |
249.1±28.7 °C
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| Vapour Pressure |
0.0±1.3 mmHg at 25°C
|
| Index of Refraction |
1.670
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| LogP |
0.96
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
17
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| Complexity |
353
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| Defined Atom Stereocenter Count |
0
|
| InChi Key |
MVJHUMZXIJPVHV-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C12H8O5/c1-15-10-6-2-3-8(13)17-12(6)9(14)11-7(10)4-5-16-11/h2-5,14H,1H3
|
| Chemical Name |
9-hydroxy-4-methoxyfuro[3,2-g]chromen-7-one
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| HS Tariff Code |
2934.99.9001
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| 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)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~430.68 mM)
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|---|---|
| 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
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] 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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.3068 mL | 21.5341 mL | 43.0682 mL | |
| 5 mM | 0.8614 mL | 4.3068 mL | 8.6136 mL | |
| 10 mM | 0.4307 mL | 2.1534 mL | 4.3068 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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