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Butylphthalide

Alias: N-butylphthalide; 3-n-Butylphthalide; Butylphthalide
Cat No.:V17278 Purity: ≥98%
Butylphthalide (3-n-Butylphthalide) is a bioactive molecule against cerebral ischemia.
Butylphthalide
Butylphthalide Chemical Structure CAS No.: 6066-49-5
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
25mg
50mg
100mg
10 mM * 1 mL in DMSO

Other Forms of Butylphthalide:

  • Butylphthalide-d3 (3-n-Butylphthalide-d3; 3-Butylphthalide-d3)
Official Supplier of:
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Top Publications Citing lnvivochem Products
Purity & Quality Control Documentation

Purity: ≥98%

Product Description
Butylphthalide (NBP; 3-n-Butylphthalide) is a bioactive molecule against cerebral ischemia. It was originally extracted from celery species and has been shown to be effective in stroke animal models. In 2002, dl-3n-butylphthalide (NBP) proved its safety and therapeutic effect on cerebral ischemia and received approval from the National Medical Products Administration (NMPA) of China for the treatment of acute ischemic stroke.
Biological Activity I Assay Protocols (From Reference)
Targets
Cerebral ischemia
ln Vitro
In the present study, a series of hydrogen sulfide (H2S) releasing derivatives (8a–g and 9a–f) of 3-n-butylphthalide (NBP) were designed, synthesized and biologically evaluated. The most promising compound 8e significantly inhibited the adenosine diphosphate (ADP) and arachidonic acid (AA)-induced platelet aggregation in vitro, superior to NBP, ticlopidine hydrochloride and aspirin. Furthermore, 8e could slowly produce moderate levels of H2S in vitro, which could be beneficial for improving cardiovascular and cerebral circulation [3].
ln Vivo
In SAMP8 mice, butylphthalide (160 mg/kg, ir) can alleviate memory and learning deficiencies [3].
Enzyme Assay
Regarding the protection of mitochondrial function, early animal studies showed that dl-NBP improves the activities of Na/K-ATPase and Ca-ATPase in the mitochondrion. As is known, Na/K-ATPase and Ca-ATPase are important enzymes that maintain cell membrane potential and participate in material transportation to regulate cell volume. NBP can maintain mitochondrial membrane fluidity and the stability of the mitochondrial membrane, preventing mitochondrial swelling [5].
Cell Assay
The main pharmacologic effects of NBP include reconstructing microcirculation, protecting mitochondrial function, inhibiting oxidative stress, inhibiting inflammatory responses, and inhibiting neuronal apoptosis. It has also been found to have effects including anti-platelet aggregation, anti-thrombosis, and anti-atherosclerosis [5].
Animal Protocol
Animal/Disease Models: Aged male SAMP8 mice and SAMR1 mice [3]
Doses: 40 mg/kg, 80 mg/kg, 160 mg/kg
Route of Administration: Orally administered daily for 60 days
Experimental Results: The escape latency on day 7 was shortened. Improved learning deficits in SAMP8 mice.
References

[1]. Ninety-day administration of dl-3-n-butylphthalide for acute ischemic stroke: a randomized, double-blind trial. Chin Med J (Engl). 2013;126(18):3405-10.

[2]. 3-N-butylphthalide improves neuronal morphology after chronic cerebral ischemia. Neural Regen Res. 2014 Apr 1;9(7):719-26.

[3]. Design, synthesis and biological evaluation of hydrogen sulfide releasing derivatives of 3-n-butylphthalide as potential antiplatelet and antithrombotic agents. Org Biomol Chem. 2014 Aug 21;12(31):5995-6004.

[4]. Improvement of cognitive deficits in SAMP8 mice by 3-n-butylphthalide. Neurol Res. 2014 Mar;36(3):224-33.

[5]. Chen XQ, Qiu K, Liu H, He Q, Bai JH, Lu W. Application and prospects of butylphthalide for the treatment of neurologic diseases. Chin Med J (Engl). 2019;132(12):1467-1477.

Additional Infomation
Butylphthalide is a member of benzofurans.
Butylphthalide has been used in trials studying the prevention of Restenosis.
Butylphthalide has been reported in Angelica gigas, Ligusticum striatum, and other organisms with data available.
See also: Celery Seed (part of); Angelica sinensis root oil (part of).
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C12H14O2
Molecular Weight
190.242
Exact Mass
190.099
Elemental Analysis
C, 75.76; H, 7.42; O, 16.82
CAS #
6066-49-5
Related CAS #
Butylphthalide-d3
PubChem CID
61361
Appearance
Colorless to light yellow liquid
Density
1.1±0.1 g/cm3
Boiling Point
312.8±31.0 °C at 760 mmHg
Flash Point
128.3±22.2 °C
Vapour Pressure
0.0±0.7 mmHg at 25°C
Index of Refraction
1.525
Source
Celery species
LogP
3.08
Hydrogen Bond Donor Count
0
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
3
Heavy Atom Count
14
Complexity
212
Defined Atom Stereocenter Count
0
SMILES
O1C(C2=C([H])C([H])=C([H])C([H])=C2C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H])=O
InChi Key
HJXMNVQARNZTEE-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-7,11H,2-3,8H2,1H3
Chemical Name
3-Butyl-2-benzofuran-1(3H)-one
Synonyms
N-butylphthalide; 3-n-Butylphthalide; Butylphthalide
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)
DMSO : ~250 mg/mL (~1314.13 mM)
H2O : ~100 mg/mL (~525.65 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (10.93 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 20.8 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: ≥ 2.08 mg/mL (10.93 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 20.8 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: ≥ 2.08 mg/mL (10.93 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 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 13.33 mg/mL (70.07 mM) in 50% PEG300 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 5.2565 mL 26.2826 mL 52.5652 mL
5 mM 1.0513 mL 5.2565 mL 10.5130 mL
10 mM 0.5257 mL 2.6283 mL 5.2565 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:

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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)
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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:
  • 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.

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  • 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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