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cis-Ferulic acid 4-O-β-D-glucopyranoside

Cat No.:V73347 Purity: ≥98%
cis-Ferulic acid 4-O-β-D-glucopyranoside (compound 7) is a phenolic glycoside extracted from Siberian white thorn.
cis-Ferulic acid 4-O-β-D-glucopyranoside
cis-Ferulic acid 4-O-β-D-glucopyranoside Chemical Structure CAS No.: 94942-20-8
Product category: Phosphatase
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
1mg
5mg
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Product Description
cis-Ferulic acid 4-O-β-D-glucopyranoside (compound 7) is a phenolic glycoside extracted from Siberian white thorn. cis-Ferulic acid 4-O-β-D-glucopyranoside has anti-oxidant effect and potent inhibitory effect on phosphatase PTP1B.
cis-Ferulic acid 4-O-β-D-glucopyranoside (compound 7) is a phenolic glycoside extracted from Siberian white thorn (Onobrychis viciifolia and Equisetum hyemale). This natural compound exhibits both potent inhibitory effects on protein tyrosine phosphatase 1B (PTP1B) and significant antioxidant activity. cis-Ferulic acid 4-O-β-D-glucopyranoside is a valuable research tool for studying PTP1B-related signaling pathways and oxidative stress mechanisms, with potential applications in diabetes and metabolic research.
Biological Activity I Assay Protocols (From Reference)
Targets
cis-Ferulic acid 4-O-β-D-glucopyranoside primarily targets protein tyrosine phosphatase 1B (PTP1B), a key negative regulator of insulin receptor signaling. By inhibiting PTP1B, the compound enhances insulin signaling and promotes glucose uptake in insulin-responsive tissues. The compound also demonstrates potent antioxidant activity, which may contribute to its overall therapeutic potential by reducing oxidative stress and protecting cells from damage. The dual PTP1B inhibitory and antioxidant activities make this compound particularly interesting for diabetes research.
ln Vitro
In vitro, cis-Ferulic acid 4-O-β-D-glucopyranoside demonstrates potent inhibition of PTP1B phosphatase activity. The compound shows concentration-dependent inhibition in biochemical assays using purified PTP1B enzyme. The compound also exhibits significant antioxidant activity, which can be measured using standard antioxidant assays such as DPPH radical scavenging or ABTS assays. The combination of PTP1B inhibition and antioxidant activity suggests potential synergistic benefits for metabolic health.
ln Vivo
In vivo activity data for cis-Ferulic acid 4-O-β-D-glucopyranoside are limited, as the compound is primarily studied in vitro. Based on its PTP1B inhibitory and antioxidant mechanisms, the compound is expected to improve glucose metabolism, insulin sensitivity, and oxidative stress in animal models of diabetes and metabolic disorders. However, detailed pharmacokinetic and efficacy studies in animal models have not been extensively reported. Further in vivo studies are needed.
Enzyme Assay
The in vitro enzyme inhibition assay for cis-Ferulic acid 4-O-β-D-glucopyranoside typically involves measuring PTP1B activity using a synthetic substrate such as p-nitrophenyl phosphate (pNPP). Purified recombinant human PTP1B enzyme is incubated with varying concentrations of the compound (0.1-100 µM) in assay buffer at 37°C for 10-15 minutes. The reaction is initiated by adding the substrate, and after incubation, the reaction is stopped. Absorbance at 405 nm is measured, and IC50 values are calculated. For antioxidant assays, DPPH or ABTS radical scavenging protocols are used.
Cell Assay
For in vitro cell-based assays, insulin-responsive cell lines or cells exposed to oxidative stress are cultured and treated with cis-Ferulic acid 4-O-β-D-glucopyranoside at concentrations ranging from 1-100 µM for 24-48 hours. PTP1B activity is measured in cell lysates using a phosphatase activity assay kit. Insulin signaling is evaluated by Western blot analysis of phosphorylated insulin receptor and Akt. Oxidative stress markers such as reactive oxygen species and lipid peroxidation are measured.
Animal Protocol
In vivo animal studies for cis-Ferulic acid 4-O-β-D-glucopyranoside have not been extensively reported. Based on the compound's mechanisms as a PTP1B inhibitor and antioxidant, potential in vivo studies would involve administration to diabetic or obese mouse models via oral gavage or intraperitoneal injection at doses ranging from 1-50 mg/kg. Efficacy would be assessed by measuring blood glucose levels, insulin sensitivity, and oxidative stress markers. Tissue samples would be collected for analysis.
ADME/Pharmacokinetics
Pharmacokinetic properties of cis-Ferulic acid 4-O-β-D-glucopyranoside have not been fully characterized. Molecular weight is 356.32 and molecular formula is C₁₆H₂₀O₉. CAS number is 94942-20-8. The compound appears as a white crystalline powder. Detailed pharmacokinetic parameters such as bioavailability, half-life, and protein binding have not been reported. Stability in solution may be limited.
Toxicity/Toxicokinetics
Toxicology data for cis-Ferulic acid 4-O-β-D-glucopyranoside are limited. As a natural phenolic glycoside, the compound is generally considered to have low toxicity, but comprehensive toxicology studies have not been conducted. The compound's antioxidant properties suggest a favorable safety profile. However, potential off-target effects and chronic toxicity remain to be evaluated. Standard in vitro toxicity assays should be performed for safety assessment.
References

[1]. Phenolic glycosides from Nitraria sibirica leaves and their in vitro biological activities. Nat Prod Res. 2021 Apr;35(8):1388-1392.

Additional Infomation
Cis-ferulic acid 4-O-β-D-glucopyranoside has been reported in Onobrychis viciifolia and Equisetum hyemale, and available data are available.
cis-Ferulic acid 4-O-β-D-glucopyranoside (compound 7) is a phenolic glycoside from Siberian white thorn with potent PTP1B inhibitory activity and antioxidant effects. The compound's dual mechanism of action makes it a valuable tool for studying insulin signaling, oxidative stress, and metabolic regulation. It shows potential for diabetes and metabolic research applications. The compound is intended for research use only and is not approved for therapeutic applications.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C16H20O9
Molecular Weight
356.324605941772
Exact Mass
356.11
CAS #
94942-20-8
PubChem CID
9820054
Appearance
White to off-white solid powder
LogP
-1.1
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
9
Rotatable Bond Count
6
Heavy Atom Count
25
Complexity
469
Defined Atom Stereocenter Count
5
SMILES
COC1=C(C=CC(=C1)/C=C\C(=O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O
InChi Key
IEMIRSXOYFWPFD-QEQKPWIDSA-N
InChi Code
InChI=1S/C16H20O9/c1-23-10-6-8(3-5-12(18)19)2-4-9(10)24-16-15(22)14(21)13(20)11(7-17)25-16/h2-6,11,13-17,20-22H,7H2,1H3,(H,18,19)/b5-3-/t11-,13-,14+,15-,16-/m1/s1
Chemical Name
(Z)-3-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]prop-2-enoic acid
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

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)
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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 : PEG300Tween 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).
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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 : PEG300Tween 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).
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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 2.8065 mL 14.0323 mL 28.0647 mL
5 mM 0.5613 mL 2.8065 mL 5.6129 mL
10 mM 0.2806 mL 1.4032 mL 2.8065 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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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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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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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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