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4-Isopropylcatechol

Alias: 4-IPC
Cat No.:V103255 Purity: ≥98%
4-Isopropylcatechol is a potent and irreversible skin depigmenting agent.
4-Isopropylcatechol
4-Isopropylcatechol Chemical Structure CAS No.: 2138-43-4
Product category: Tyrosinase
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
5mg
10mg
Other Sizes
Official Supplier of:
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Product Description
4-Isopropylcatechol is a potent and irreversible skin depigmenting agent. 4-Isopropylcatechol significantly inhibits protein biosynthesis in mouse melanoma cells that contain high levels of tyrosinase. 4-Isopropylcatechol can be used to study skin hyperpigmentation.
4-Isopropylcatechol (4-IPC) is a 4-alkyl-substituted catechol derivative that functions as a potent and irreversible cutaneous depigmenting (skin-whitening) agent. It is a small-molecule research tool used to study melanogenesis, the process of melanin (skin pigment) production. Its primary application is in research related to hyperpigmentation disorders, such as melasma, freckles, and age spots. It is for research use only and not for human cosmetic or therapeutic purposes.
Biological Activity I Assay Protocols (From Reference)
Targets
The primary target of 4-Isopropylcatechol is the enzyme tyrosinase, which is the rate-limiting enzyme in the melanin biosynthesis pathway. It acts as an inhibitor of tyrosinase, leading to a reduction in melanin production. The exact binding mode is not fully detailed, but the compound is described as having an irreversible mechanism of action.
ln Vitro
4-Isopropylcatechol has been shown to significantly inhibit protein biosynthesis in mouse melanoma cells that contain high levels of tyrosinase. This demonstrates its direct cellular effect on the machinery responsible for melanin production. The compound's activity is dose-dependent and can be measured by quantifying the reduction in melanin content in treated cells.
ln Vivo
No specific in vivo data for 4-Isopropylcatechol was found. As a potent tyrosinase inhibitor, it is used in research models to reduce pigmentation. A typical in vivo application would be to topically apply the compound to the skin of an animal model (e.g., guinea pig or mouse) to test its skin-lightening efficacy. The resulting reduction in skin pigmentation would be measured by histology or a chromameter.
Enzyme Assay
A typical in vitro tyrosinase enzyme inhibition assay: L-tyrosine (0.5 mg/mL) is prepared in 50 mM phosphate buffer (pH 6.8). 4-Isopropylcatechol is serially diluted in DMSO and added to a 96-well plate at final concentrations ranging from 1 to 500 microM. Mushroom tyrosinase (100 units/mL) is added to each well, except for the blank. The plate is incubated at 37degC for 30 minutes. The reaction product (dopaquinone) is measured by absorbance at 475 nm. The percent inhibition is calculated relative to a control without the compound. A standard cell-based melanogenesis assay: B16F10 mouse melanoma cells are cultured in DMEM with 10% FBS and 1% penicillin/streptomycin. To induce melanin synthesis, the cells are treated with 100 nM alpha-melanocyte-stimulating hormone (alpha-MSH). 4-Isopropylcatechol (0.1-50 microM) is added to the culture medium for 72 hours. After treatment, the cells are harvested, lysed in 1N NaOH, and the absorbance is measured at 405 nm to quantify melanin content. Cell viability is determined simultaneously via MTT assay to ensure that the effects are not due to cytotoxicity.
Animal Protocol
No in vivo animal protocol was found for 4-Isopropylcatechol. A general protocol for evaluating depigmenting agents in vivo: 6-8 week old female guinea pigs are depilated on their dorsal skin. The test compound (e.g., 1%, 2%, 5% in a water-in-oil cream base) is applied topically to the designated area (e.g., 2x2 cm) once daily for 4-6 weeks. A control area receives only the vehicle. Skin pigmentation is measured weekly using a colorimeter (e.g., *a* value for erythema, *L* value for lightness). At the end of the study, skin biopsies are taken for histochemical staining (e.g., Fontana-Masson stain) to visualize melanin in the epidermis.
ADME/Pharmacokinetics
Not applicable. 4-Isopropylcatechol is a topical research agent. Its systemic pharmacokinetics (absorption, distribution, metabolism, and excretion) would not be studied in the same way as an oral drug. If applied topically, it may be absorbed through the skin. However, as a tool compound, its use is limited to in vitro or ex vivo settings.
Toxicity/Toxicokinetics
Dermal and systemic toxicity data are not available in the provided literature. As a tyrosinase inhibitor, its primary toxicity would likely be related to its depigmenting effect. It should be handled with caution, as catechols are known skin irritants and sensitizers. It is a research chemical and is not intended for human or veterinary use.
References

[1]. Tyrosinase-mediated inhibition of in vitro leucine incorporation into mouse melanoma by 4-isopropylcatechol. Cancer Res. 1975 Nov;35(11 Pt 1):3126-30.

[2]. Bleehen SS. The treatment of hypermelanosis with 4-isopropylcatechol. Br J Dermatol. 1976 Jun;94(6):687-94.

Additional Infomation
4-Isopropylcatechol is a research-grade compound for laboratory use only. Its CAS number is 2138-43-4, molecular formula is C9H12O2, and molecular weight is 152.19. It typically appears as an off-white to light yellow solid and should be stored in a cool, dry place. This product is not intended for human use and should be handled according to standard safety protocols for chemical reagents. Each product in one row, fields tab-separated.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C9H12O2
Molecular Weight
152.19
Exact Mass
152.084
CAS #
2138-43-4
PubChem CID
16497
Appearance
Off-white to light yellow solid powder
Density
1.116g/cm3
Boiling Point
271ºC at 760mmHg
Flash Point
129.2ºC
Vapour Pressure
0.00399mmHg at 25°C
Index of Refraction
1.561
LogP
2.221
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
2
Rotatable Bond Count
1
Heavy Atom Count
11
Complexity
123
Defined Atom Stereocenter Count
0
SMILES
CC(C1C=CC(O)=C(O)C=1)C
InChi Key
WYVMDJWLFVQZAL-UHFFFAOYSA-N
InChi Code
InChI=1S/C9H12O2/c1-6(2)7-3-4-8(10)9(11)5-7/h3-6,10-11H,1-2H3
Chemical Name
4-propan-2-ylbenzene-1,2-diol
Synonyms
4-IPC
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: Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
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 : ~50 mg/mL (~328.53 mM; with ultrasonication)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 1.25 mg/mL (8.21 mM)(saturation unknown) in 10% DMSO 40% PEG300 5% Tween-80 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 12.5 mg/mL clear DMSO stock solution and add it to 400 μL PEG300, mix well; then add 50 μL Tween-80 to the above system, mix well; then continue to add 450 μL of normal saline to make up to 1 mL. Preparation of normal saline: Dissolve 0.9 g of sodium chloride in ddH₂O and make up to 100 mL to obtain a clear and transparent normal saline solution.

Solubility in Formulation 2: ≥ 1.25 mg/mL (8.21 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 12.5 mg/mL clear DMSO stock solution and add it to 900 μL of 20% SBE-β-CD saline solution and mix well. 2 g SBE-β-CD (sulfobutyl ether β-cyclodextrin) powder is diluted to 10 mL of saline and completely dissolved until clear and transparent.

Solubility in Formulation 3: ≥ 1.25 mg/mL (8.21 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 12.5 mg/mL clear DMSO stock solution and add it to 900 μL corn oil and mix well.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 6.5707 mL 32.8537 mL 65.7073 mL
5 mM 1.3141 mL 6.5707 mL 13.1415 mL
10 mM 0.6571 mL 3.2854 mL 6.5707 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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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)
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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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