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6-O-Isobutyrylbritannilactone

Cat No.:V52483 Purity: ≥98%
6-O-Isobutyrylbritannilactone is a natural melanogenesis inhibitor.
6-O-Isobutyrylbritannilactone
6-O-Isobutyrylbritannilactone Chemical Structure CAS No.: 1259933-02-2
Product category: Epigenetic Reader Domain
This product is for research use only, not for human use. We do not sell to patients.
Size Price
500mg
1g
Other Sizes
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Product Description
6-O-Isobutyrylbritannilactone is a natural melanogenesis inhibitor. 6-O-Isobutyrylbritannilactone is a sesquiterpene extracted from chrysanthemum flowers. 6-O-Isobutyrylbritannilactone inhibits IBMX induces melanin production in B16F10 cells. 6-O-Isobutyrylbritannilactone also regulates ERK, PI3K/AKT and CREB and displays anti-melanogen activity in a zebrafish embryo model.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
6-O-Isobutyrylbritannilactone (5-100 μM; 48 h) in comparison to IBMX (100 μM; 24 h)[1]. 6-O-isobutyrylbritannilactone (5-30 μM; 12 h) suppresses albino-related mRNA levels in B16F10 cells treated with IBMX (100 μM; 48 h) in a dose-dependent manner[1]. 6-O-isobutyrylbritannilactone (20 μM; 1-9 h) suppresses phosphorylation of ERK, AKT, and CREB in a time-dependent manner [1].
ln Vivo
In comparison to untreated controls, 6-O-isobutyrylbritannilactone (10-100 μM; 48 h) dramatically lowers pigmentation in zebrafish embryos [1].
Cell Assay
RT-PCR[1]
Cell Types: B16F10 cells
Tested Concentrations: 5 μM, 10 μM, 20 μM, 30 μM
Incubation Duration: 12 hrs (hours); with 100 μM IBMX for 48 hrs (hours)
Experimental Results: Inhibited whitening-related mRNA levels, and resulted in completely inhibited expressions of melanogenesis-related protein levels at 20 μM.

Western Blot Analysis[1]
Cell Types: 20 μM
Tested Concentrations: 5 μM, 10 μM, 20 μM, 30 μM
Incubation Duration: 1 h, 3 h, 6 h, and 9 h
Experimental Results: Inhibited the phosphorylation of ERK, AKT, and CREB. Demonstrated the melanogenesis suppression induced by IBMX via inaction of multiple signaling pathways.

Cell Cytotoxicity Assay[1]
Cell Types: B16F10 cells
Tested Concentrations: 5 μM, 10 μM, 20 μM, 50 μM, and 100 μM
Incubation Duration: 24 hrs (hours)
Experimental Results: Inhibited B16F10 cells viability in a dose-dependent manner.
Animal Protocol
Animal/Disease Models: Zebrafish embryos[1]
Doses: 10 μM, 50 μM, and 100 μM
Route of Administration: Dipped in culture for 48 hrs (hours)
Experimental Results: diminished pigmentation by approximately 8%, 13%, and 16%.
References

[1]. Anti-Melanogenesis Activity of 6-O-Isobutyrylbritannilactone from Inula britannica on B16F10 Melanocytes and In Vivo Zebrafish Models. Molecules. 2020 Aug 26;25(17):3887.

Additional Infomation
(3aR)-3-Methylene-4alpha-(isobutyryloxy)-5beta-[(S)-1-methyl-4-hydroxybutyl]-6-methyl-2,3,3aalpha,4,7,7aalpha-hexahydrobenzofuran-2-one has been reported in Inula japonica and Pentanema britannicum with data available.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C19H28O5
Molecular Weight
336.42
Exact Mass
336.193
CAS #
1259933-02-2
PubChem CID
50917934
Appearance
Typically exists as solid at room temperature
LogP
2.4
Hydrogen Bond Donor Count
1
Hydrogen Bond Acceptor Count
5
Rotatable Bond Count
7
Heavy Atom Count
24
Complexity
560
Defined Atom Stereocenter Count
4
SMILES
CC1=C([C@H]([C@H]2[C@@H](C1)OC(=O)C2=C)OC(=O)C(C)C)[C@@H](C)CCCO
InChi Key
RIFCMNAQMNUNKD-ASTDHERZSA-N
InChi Code
InChI=1S/C19H28O5/c1-10(2)18(21)24-17-15(11(3)7-6-8-20)12(4)9-14-16(17)13(5)19(22)23-14/h10-11,14,16-17,20H,5-9H2,1-4H3/t11-,14+,16+,17+/m0/s1
Chemical Name
[(3aR,4S,7aR)-5-[(2S)-5-hydroxypentan-2-yl]-6-methyl-3-methylidene-2-oxo-3a,4,7,7a-tetrahydro-1-benzofuran-4-yl] 2-methylpropanoate
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 2.9725 mL 14.8624 mL 29.7247 mL
5 mM 0.5945 mL 2.9725 mL 5.9449 mL
10 mM 0.2972 mL 1.4862 mL 2.9725 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.

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:
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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Definitions of molecular mass, molecular weight, molar mass and molar weight:
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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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