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Pinostilbene

Cat No.:V40629 Purity: ≥98%
Pinostilbene (trans-Pinostilbene) is a major metabolite of Pterostilbene.
Pinostilbene
Pinostilbene Chemical Structure CAS No.: 42438-89-1
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Pinostilbene (trans-Pinostilbene) is a major metabolite of Pterostilbene. Pinostilbene has inhibitory activities on colon cancer/tumor cells.
Pinostilbene (CAS#: 42438-89-1) is a naturally occurring stilbenoid that is a major metabolite of Pterostilbene and a methylated derivative of resveratrol. It is isolated from the seeds of Vitis riparia. Pinostilbene exhibits a broad spectrum of bioactivity, displaying cytotoxic effects against various cancer cell lines. It markedly attenuates the phosphorylation of JNK and c-Jun triggered by 6-OHDA and shows protective effects against 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y cells.
Biological Activity I Assay Protocols (From Reference)
Targets
Pinostilbene targets multiple pathways. It is an effective enzyme inhibitor, showing potent inhibition of recombinant human CYP1B1 with IC50 and Ki values of 2100 nM and 900 nM, respectively, and CYP1A1 with a Ki value of 120 nM. It attenuates the phosphorylation of JNK and c-Jun triggered by 6-OHDA. Pinostilbene exhibits inhibitory effects on colon cancer cells and has protective effects against neurotoxicity. It also scavenges DPPH radicals with an IC50 of 47.1 μM.
ln Vitro
Normal colon cell proliferation is not significantly inhibited by pinosinbene (0–40 μM; 24–48 hours) [1]. When compared to control cells, pinostilbene (20 μM, 40 μM; 24 hours, 48 hours) significantly and dose-dependently increases the percentage of S phase cells in HCT116 and HT29 cells [1]. A significant increase in the number of G2/M phase cells in HT29 cells can also be induced by μM of pine stilbene [1]. Pinostilbene (20 μM, 40 μM; 24 h, 48 h) controls the expression of important signaling proteins linked to both apoptosis and cell growth [1]. In addition, pinosinbene functions as a methylated resveratrol derivative and shields SH-SY5Y cells from the neurotoxicity caused by 6-hydroxydopamine [2].
In vitro, pinostilbene exhibits cytotoxic effects against various cancer cell lines with differing potencies. It shows inhibitory effects on colon cancer cells. At 0.1-10 μM, pinostilbene reduces neurotoxicity in SH-SY5Y cells induced by the parkinsonian mimetic 6-hydroxydopamine. It reduces the release of lactate dehydrogenase and activity of caspase-3 triggered by 6-OHDA in a dose-dependent manner. Pinostilbene scavenges DPPH radicals with an IC50 of 47.1 μM. It inhibits CYP1B1 (IC50 = 2100 nM, Ki = 900 nM) and CYP1A1 (Ki = 120 nM).
ln Vivo
In vivo, pinostilbene has been studied for its potential therapeutic effects in cancer and neurodegenerative diseases. As a metabolite of pterostilbene and a resveratrol derivative, it may share some of the in vivo benefits of these compounds, including antioxidant and anticancer activities. However, specific in vivo efficacy data, including dosing regimens and animal models, are not extensively detailed in the available literature. Further studies are needed to fully characterize its in vivo pharmacological profile.
Enzyme Assay
Cell-free assays for pinostilbene involve evaluating its enzyme inhibitory activity and antioxidant properties. CYP1B1 and CYP1A1 inhibition is assessed using standard cytochrome P450 activity assays with fluorescent or luminescent substrates. Antioxidant activity is measured using DPPH radical scavenging assays. IC50 and Ki values are determined from dose-response curves. The compound's chemical purity and identity are confirmed by HPLC and NMR analysis. It is typically dissolved in DMSO or ethanol for assay preparation.
Cell Assay
Cell viability assay [1]
Cell Types: HCT116 cells, HT29 cells
Tested Concentrations: 24 hrs (hours), 48 hrs (hours)
Incubation Duration: 0-100 μM
Experimental Results: Inhibited the growth of two human colon cancer cells.
Apoptosis analysis [1]
Cell Types: HCT116 cells, HT29 cells
Tested Concentrations: 20 μM, 40 μM
Incubation Duration: 24 hrs (hours), 48 hrs (hours)
Experimental Results: resulted in a significant and dose-dependent increase in the percentage of cells in S phase.
Cell viability assay [1]
Cell Types: HCT116 Cell
Tested Concentrations: 20 μM, 40 μM
Incubation Duration: 24 hrs (hours), 48 hrs (hours)
Experimental Results: The expression levels of p53, Bax, cleaved caspase-3, cleaved PARP and p21Cip1/Waf1 increased Dramatically, At the same time, the expression levels of cyclin E and p-Rb were diminished.
In vitro cellular assays for pinostilbene typically involve treating cancer cell lines or SH-SY5Y neuroblastoma cells with various concentrations of the compound. For neurotoxicity studies, cells are pre-treated with pinostilbene (0.1-10 μM) before exposure to 6-hydroxydopamine. Cell viability is assessed using MTT or LDH release assays. Apoptosis is evaluated using caspase-3 activity assays. JNK and c-Jun phosphorylation is assessed by western blotting. Dose-response curves are generated to determine IC50 values.
Animal Protocol
In vivo animal studies for pinostilbene are conducted in models of cancer and neurodegenerative disease. The compound is administered via various routes including oral gavage or intraperitoneal injection. Tumor growth is monitored in cancer models. Neuroprotection is assessed in models of Parkinson's disease. However, specific dosing regimens and experimental protocols are not extensively documented in the available literature. Standard protocols for evaluating anticancer and neuroprotective agents would typically be employed.
ADME/Pharmacokinetics
Pharmacokinetic properties of pinostilbene include a molecular weight of 242.27 g/mol and molecular formula C15H14O3. As a natural product and metabolite of pterostilbene, it is expected to have moderate oral bioavailability and tissue penetration. The compound is typically stored at appropriate conditions as a research reagent. Detailed ADME parameters such as half-life, Cmax, and AUC are not extensively reported in the available literature.
Toxicity/Toxicokinetics
The toxicity profile of pinostilbene has not been extensively characterized in published literature. As a naturally occurring compound, it is generally considered to have a favorable safety profile at research doses. Standard preclinical safety studies would include acute and sub-chronic toxicity assessments in rodent models. The compound is intended for research use only and not for therapeutic applications in humans. Standard safety precautions should be followed when handling this compound.
References

[1]. Identification of pinostilbene as a major colonic metabolite of pterostilbene and its inhibitory effects on colon cancer cells. Mol Nutr Food Res. 2016 Sep;60(9):1924-32.

[2]. Protective effects of pinostilbene, a resveratrol methylated derivative, against 6-hydroxydopamine-induced neurotoxicity in SH-SY5Y cells. J Nutr Biochem. 2010 Jun;21(6):482-9.

Additional Infomation
3-Methoxy-4',5-Dihydroxy-trans-stilbene is a stilbene compound, a derivative of trans-resveratrol, in which one of the meta-hydroxyl groups is converted to the corresponding methyl ether. It is functionally related to trans-resveratrol. 3-Methoxy-4',5-Dihydroxy-trans-stilbene has been reported in soybean (Soymida febrifuga), Streptomyces avermitilis, and other organisms with relevant data.
Pinostilbene is a naturally occurring stilbenoid and major metabolite of pterostilbene. It exhibits cytotoxic effects against cancer cell lines and inhibits CYP1B1 (IC50 = 2100 nM, Ki = 900 nM) and CYP1A1 (Ki = 120 nM). Pinostilbene (0.1-10 μM) reduces 6-OHDA-induced neurotoxicity in SH-SY5Y cells and scavenges DPPH radicals (IC50 = 47.1 μM). It is a research tool for studying cancer, neuroprotection, and enzyme inhibition.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H14O3
Molecular Weight
242.2699
Exact Mass
242.094
CAS #
42438-89-1
PubChem CID
5473050
Appearance
Off-white to light yellow solid powder
Density
1.3±0.1 g/cm3
Boiling Point
454.3±33.0 °C at 760 mmHg
Melting Point
117-118℃
Flash Point
228.5±25.4 °C
Vapour Pressure
0.0±1.2 mmHg at 25°C
Index of Refraction
1.692
LogP
3.8
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
3
Heavy Atom Count
18
Complexity
269
Defined Atom Stereocenter Count
0
SMILES
COC1=CC(=CC(=C1)O)/C=C/C2=CC=C(C=C2)O
InChi Key
KUWZXOMQXYWKBS-NSCUHMNNSA-N
InChi Code
InChI=1S/C15H14O3/c1-18-15-9-12(8-14(17)10-15)3-2-11-4-6-13(16)7-5-11/h2-10,16-17H,1H3/b3-2+
Chemical Name
3-[(E)-2-(4-hydroxyphenyl)ethenyl]-5-methoxyphenol
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 Data
Solubility (In Vitro)
DMSO : ~33.33 mg/mL (~137.57 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.32 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.5 mg/mL (10.32 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
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.

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Solubility in Formulation 3: ≥ 2.5 mg/mL (10.32 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 4.1276 mL 20.6381 mL 41.2763 mL
5 mM 0.8255 mL 4.1276 mL 8.2553 mL
10 mM 0.4128 mL 2.0638 mL 4.1276 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.

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An example of molarity calculation using the molarity calculator is shown below:
What is the mass of compound required to make a 10 mM stock solution in 5 ml of DMSO given that the molecular weight of the compound is 350.26 g/mol?
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  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
Using the equation C1V1 = C2V2, where C1=10 mM, C2=25 μM, V2=25 ml and V1 is the unknown:
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  • The answer of 62.5 μL (0.1 ml) appears in the Volume (Start) box
g/mol

Molecular Weight Calculator allows you to calculate the molar mass and elemental composition of a compound, as detailed below:

Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
Instructions to calculate molar mass (molecular weight) of a chemical compound:
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
Step 2: Enter in vivo formulation (This is only a calculator, not the exact formulation for a specific product. Please contact us first if there is no in vivo formulation in the solubility section.)
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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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