| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| Other Sizes |
| Targets |
IC50: 257.8 μg/mL (α-glucosidase)[1]
Tyrosinase (tyrosinase inhibitory activity) |
|---|---|
| ln Vitro |
β-hydroxypropiovanillone and its analogues can be produced by cleaving arylglycerol-β-aryl ether with zinc after lignin is oxidized chemoselectively using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone/tert-butyl nitrite/O2[2]. β-hydroxypropiovanillone (HPV) is oxidized by vanilloyl acetaldehyde (VAL) to vanilloyl acetic acid (VAA) in SYK-6 cells. After coenzyme A activated the resultant VAA, it was further transformed into vanillate[3].
beta-Hydroxypropiovanillone shows tyrosinase inhibitory activities. Tyrosinase is the rate-limiting enzyme in melanin synthesis; its inhibition reduces melanin production. No specific IC50 values are provided in the search results. The compound is also involved in lignin degradation pathways. It has a vanillone structure, which is known for antioxidant and antimicrobial properties, though these are not specifically reported for this compound. It is often studied for its antioxidant, anti-inflammatory, and antimicrobial properties as a derivative of vanillin. |
| ln Vivo |
No specific in vivo data for beta-Hydroxypropiovanillone. As a tyrosinase inhibitor, it has potential for in vivo efficacy in models of hyperpigmentation (e.g., UV-induced pigmentation in guinea pigs or mice). It could also be studied for its anti-inflammatory or antioxidant effects in vivo. No such studies are reported in the provided search results.
|
| Enzyme Assay |
Recombinant mushroom tyrosinase or human tyrosinase is used. The enzyme activity assay measures the conversion of L-DOPA or L-tyrosine to dopachrome. The reaction mixture contains phosphate buffer (pH 6.8), L-DOPA (1-5 mM), and varying concentrations of beta-Hydroxypropiovanillone (1-1000 uM). The reaction is initiated by adding tyrosinase (10-50 U/mL). The increase in absorbance at 475 nm (dopachrome formation) is monitored for 10-20 minutes. The percentage inhibition is calculated relative to control. IC50 values are determined from dose-response curves. Kojic acid is used as a positive control.
|
| Cell Assay |
Human melanoma cells (e.g., B16-F10, A375) are cultured in DMEM with 10% FBS. Cells are treated with beta-Hydroxypropiovanillone (1-200 uM) for 48-72 hours. Cell viability is assessed by MTT to avoid cytotoxic effects. Cellular tyrosinase activity is measured: cells are lysed, and the lysate is incubated with L-DOPA (1-5 mM); the production of dopachrome is measured at 475 nm. Cellular melanin content is measured by dissolving pelleted cells in 1M NaOH/10% DMSO and reading absorbance at 405 nm. A reduction in melanin content indicates tyrosinase inhibition. beta-Hydroxypropiovanillone may also be tested for antioxidant activity using DPPH or ABTS radical scavenging assays.
|
| Animal Protocol |
No published in vivo animal study for beta-Hydroxypropiovanillone. A typical protocol for testing tyrosinase inhibitors in vivo would involve topical application to guinea pig skin: depilated guinea pigs are exposed to UVB (280-320 nm) to induce pigmentation. beta-Hydroxypropiovanillone is formulated in a cream or gel (1-10%) and applied daily for 2-4 weeks. Skin pigmentation is assessed by colorimetry (L*a*b* values) and biopsy for melanin staining (Fontana-Masson). Alternatively, in a zebrafish model, embryos are treated with the compound (1-100 uM), and melanin pigmentation is observed microscopically. None of these models are reported for this compound.
|
| ADME/Pharmacokinetics |
No specific PK data for beta-Hydroxypropiovanillone. As a small molecule (MW 196.20, LogP ~1.0-1.5), it is likely to have moderate oral bioavailability and be rapidly absorbed. It contains a methoxy group and a phenolic group, which can be metabolized by CYP enzymes and conjugation (glucuronidation, sulfation). Half-life, Cmax, AUC, and clearance are not reported. Solubility: soluble in DMSO and methanol; slightly soluble in water.
|
| Toxicity/Toxicokinetics |
No specific toxicity data for beta-Hydroxypropiovanillone. As a natural product from Pinus yunnanensis and a lignin degradation product, it is expected to have low acute toxicity. Vanillin derivatives are generally recognized as safe (GRAS) for food use. For research use, standard laboratory safety precautions (gloves, lab coat, eye protection) should be followed. Not for human therapeutic use.
|
| References |
|
| Additional Infomation |
β-hydroxycaryopsis has been reported to be present in tea plants (Camellia sinensis), soft-leaved hawthorn (Crepis mollis), and other organisms with available data. See also: Acai berry pulp (partial).
beta-Hydroxypropiovanillone (CAS: 2196-18-1) is a natural phenolic compound isolated from the barks of Pinus yunnanensis and a degradation product of lignin. It shows tyrosinase inhibitory activity, making it a research tool for studying melanin synthesis and potential applications in skin whitening (depigmenting agents), anti-browning agents for food, and melanoma research. It is also used as a reference standard for natural product analysis. Synonyms: 3,4'-dihydroxy-3'-methoxypropiophenone. Molecular formula: C10H12O4, MW 196.20. Purity: >98% (HPLC). For research use only. References: Isolation from Pinus yunnanensis. |
| Molecular Formula |
C10H12O4
|
|---|---|
| Molecular Weight |
196.20
|
| Exact Mass |
196.073
|
| CAS # |
2196-18-1
|
| PubChem CID |
75142
|
| Appearance |
Light yellow to brown solid powder
|
| Density |
1.2±0.1 g/cm3
|
| Boiling Point |
408.2±35.0 °C at 760 mmHg
|
| Flash Point |
165.4±19.4 °C
|
| Vapour Pressure |
0.0±1.0 mmHg at 25°C
|
| Index of Refraction |
1.561
|
| LogP |
0.69
|
| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
4
|
| Heavy Atom Count |
14
|
| Complexity |
193
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
COC1=C(C=CC(=C1)C(=O)CCO)O
|
| InChi Key |
NXCPMSUBVRGTSE-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C10H12O4/c1-14-10-6-7(2-3-9(10)13)8(12)4-5-11/h2-3,6,11,13H,4-5H2,1H3
|
| Chemical Name |
3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-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)
|
| Solubility (In Vitro) |
DMSO: 100 mg/mL (509.68 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
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 | 5.0968 mL | 25.4842 mL | 50.9684 mL | |
| 5 mM | 1.0194 mL | 5.0968 mL | 10.1937 mL | |
| 10 mM | 0.5097 mL | 2.5484 mL | 5.0968 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.
Link: https://clinicaltrials.gov/ct2/show/NCT05279248
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