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Secoisolariciresinol

Cat No.:V31039 Purity: ≥98%
Secoisolariciresinol is a lignan that belongs to the phenylpropanoid group.
Secoisolariciresinol
Secoisolariciresinol Chemical Structure CAS No.: 29388-59-8
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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Other Forms of Secoisolariciresinol:

  • (R,R)-Secoisolariciresinol diglucoside-d6
  • Secoisolariciresinol diglucoside
  • Secoisolarisiresinol diglucoside
  • Secoisolariciresinol Monoglucoside
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Top Publications Citing lnvivochem Products
Product Description
Secoisolariciresinol is a lignan that belongs to the phenylpropanoid group.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
- Secoisolariciresinol showed significant DPPH radical scavenging activity with an IC50 value of 28.4 ± 1.2 μM, which was comparable to the positive control (ascorbic acid, IC50 = 22.1 ± 0.8 μM) [1]
- In the ABTS cation radical scavenging assay, Secoisolariciresinol exhibited dose-dependent activity, with a scavenging rate of 89.6 ± 2.3% at 100 μM, and an IC50 value of 31.7 ± 1.5 μM [1]
- The compound displayed moderate ferric reducing antioxidant power (FRAP), with a reducing capacity of 1.24 ± 0.08 mmol Fe²⁺/g at 100 μM [1]
- Secoisolariciresinol showed weak ferrous ion chelating activity, with a chelating rate of 32.8 ± 2.1% at 200 μM [1]
- Gastrointestinal stability assay revealed that Secoisolariciresinol was stable in simulated gastric fluid (pH 1.2) with a residual rate of 92.3 ± 3.1% after 2 hours of incubation. In simulated intestinal fluid (pH 6.8), the residual rate was 87.6 ± 2.8% after 4 hours of incubation [1]
ln Vivo
- In mice treated with Secoisolariciresinol (oral administration at 50, 100, and 200 mg/kg body weight) for 7 consecutive days, the serum superoxide dismutase (SOD) activity was significantly increased by 28.5%, 42.3%, and 56.7%, respectively, compared to the control group [1]
- The hepatic catalase (CAT) activity in treated mice was elevated by 24.6% (50 mg/kg), 38.9% (100 mg/kg), and 51.2% (200 mg/kg) compared to the control, with a dose-dependent trend [1]
- Secoisolariciresinol significantly reduced the malondialdehyde (MDA) content in mouse serum and liver. At 200 mg/kg, serum MDA was decreased by 48.9% and hepatic MDA by 53.4% compared to the control group [1]
- The glutathione (GSH) level in mouse liver was increased by 31.2% (50 mg/kg), 45.8% (100 mg/kg), and 62.3% (200 mg/kg) after administration of Secoisolariciresinol [1]
Enzyme Assay
- DPPH radical scavenging assay: A series of dilutions of Secoisolariciresinol (10–100 μM) were mixed with DPPH radical solution. The mixture was incubated in the dark at room temperature for 30 minutes, and the absorbance was measured at 517 nm. The scavenging rate was calculated, and the IC50 value was determined by regression analysis [1]
- ABTS radical cation scavenging assay: ABTS radical cation was generated by reacting ABTS with potassium persulfate. Secoisolariciresinol solutions (10–100 μM) were added to the radical solution, incubated for 15 minutes at room temperature, and absorbance was measured at 734 nm. The scavenging rate and IC50 value were calculated [1]
- FRAP assay: Secoisolariciresinol samples (20–100 μM) were mixed with FRAP reagent (containing ferric tripyridyltriazine complex) and incubated at 37°C for 30 minutes. The absorbance was measured at 593 nm, and the reducing capacity was calculated using a ferrous sulfate standard curve [1]
- Ferrous ion chelating assay: Secoisolariciresinol solutions (50–200 μM) were mixed with ferrous chloride solution and ferrozine reagent. After incubation at room temperature for 10 minutes, the absorbance was measured at 562 nm, and the chelating rate was calculated [1]
Animal Protocol
- In vivo antioxidant activity assay: Male ICR mice (20–25 g) were randomly divided into control group (distilled water) and Secoisolariciresinol treatment groups (50, 100, 200 mg/kg body weight). The compound was dissolved in 0.5% carboxymethylcellulose sodium (CMC-Na) and administered orally once daily for 7 consecutive days. On the 8th day, mice were anesthetized, and serum and liver tissues were collected for the determination of SOD, CAT, MDA, and GSH levels [1]
ADME/Pharmacokinetics
Gastrointestinal stability: Secoisolariciresinol was incubated with gentle shaking in simulated gastric fluid (pH 1.2, containing pepsin) at 37°C. Samples were taken at 0, 0.5, 1 and 2 hours, and the residues of the compound were quantitatively analyzed by high performance liquid chromatography (HPLC). For simulated intestinal fluid (pH 6.8, containing pancreatin), incubation was performed at 0, 1, 2, 3 and 4 hours, and the residues of Secoisolariciresinol were determined by high performance liquid chromatography (HPLC) [1]
References

[1]. Identification, in vitro and in vivo Antioxidant Activity, and Gastrointestinal Stability of Lignans from Silver Fir (Abies alba) Wood Extract. Journal of Wood Chemistry and Technology. 2017 Jan, 467-477.

Additional Infomation
(-)-secoisolariciresinol is the enantiomer of secoisolariciresinol, with the (-)-(2R,3R)- configuration. It possesses antidepressant, phytometrogenic, and phytoestrogenic activities. It is the enantiomer of (+)-secoisolariciresinol. Secoisolariciresinol has been used in clinical trials for breast cancer prevention. It has been reported to be found in tea (Camellia sinensis) and radish (Raphanus sativus), as well as other organisms with relevant data.
- Secoisolariciresinol is a lignan compound isolated from the wood extract of Abies alba [1]
- Secoisolariciresinol has antioxidant mechanisms including scavenging free radicals (DPPH, ABTS), enhancing the activity of endogenous antioxidant enzymes (SOD, CAT), increasing GSH levels, and inhibiting lipid peroxidation (reducing MDA production) [1]
- Secoisolariciresinol has good gastrointestinal stability, indicating its potential for oral administration and improving in vivo bioavailability [1]
- Secoisolariciresinol helps to improve the overall antioxidant activity of Abies alba wood extract, supporting its potential application as a natural antioxidant [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C20H26O6
Molecular Weight
362.4168
Exact Mass
362.172
CAS #
29388-59-8
Related CAS #
Secoisolariciresinol diglucoside;257930-74-8;(R,R)-Secoisolariciresinol diglucoside;158932-33-3;Secoisolariciresinol Monoglucoside;63320-67-2
PubChem CID
65373
Appearance
White to off-white solid powder
Density
1.3±0.1 g/cm3
Boiling Point
609.1±55.0 °C at 760 mmHg
Melting Point
112-114ºC
Flash Point
322.1±31.5 °C
Vapour Pressure
0.0±1.8 mmHg at 25°C
Index of Refraction
1.599
LogP
0.98
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
6
Rotatable Bond Count
9
Heavy Atom Count
26
Complexity
357
Defined Atom Stereocenter Count
2
SMILES
COC1=C(C=CC(=C1)C[C@@H](CO)[C@@H](CC2=CC(=C(C=C2)O)OC)CO)O
InChi Key
PUETUDUXMCLALY-HOTGVXAUSA-N
InChi Code
InChI=1S/C20H26O6/c1-25-19-9-13(3-5-17(19)23)7-15(11-21)16(12-22)8-14-4-6-18(24)20(10-14)26-2/h3-6,9-10,15-16,21-24H,7-8,11-12H2,1-2H3/t15-,16-/m0/s1
Chemical Name
(2R,3R)-2,3-bis[(4-hydroxy-3-methoxyphenyl)methyl]butane-1,4-diol
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 : ~100 mg/mL (~275.92 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 : 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 2.7592 mL 13.7961 mL 27.5923 mL
5 mM 0.5518 mL 2.7592 mL 5.5185 mL
10 mM 0.2759 mL 1.3796 mL 2.7592 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.

Calculator

Molarity Calculator allows you to calculate the mass, volume, and/or concentration required for a solution, as detailed below:

  • Calculate the Mass of a compound required to prepare a solution of known volume and concentration
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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?
  • Enter 350.26 in the Molecular Weight (MW) box
  • Enter 10 in the Concentration box and choose the correct unit (mM)
  • Enter 5 in the Volume box and choose the correct unit (mL)
  • Click the “Calculate” button
  • The answer of 17.513 mg appears in the Mass box. In a similar way, you may calculate the volume and concentration.

Dilution Calculator allows you to calculate how to dilute a stock solution of known concentrations. For example, you may Enter C1, C2 & V2 to calculate V1, as detailed below:

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:
  • Enter 10 into the Concentration (Start) box and choose the correct unit (mM)
  • Enter 25 into the Concentration (End) box and select the correct unit (mM)
  • Enter 25 into the Volume (End) box and choose the correct unit (mL)
  • Click the “Calculate” button
  • 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:
  • Molecular mass (or molecular weight) is the mass of one molecule of a substance and is expressed in the unified atomic mass units (u). (1 u is equal to 1/12 the mass of one atom of carbon-12)
  • Molar mass (molar weight) is the mass of one mole of a substance and is expressed in g/mol.
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Reconstitution Calculator allows you to calculate the volume of solvent required to reconstitute your vial.

  • Enter the mass of the reagent and the desired reconstitution concentration as well as the correct units
  • Click the “Calculate” button
  • The answer appears in the Volume (to add to vial) box
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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