4-Methoxyphenol
Synonym(s):MEHQ;4-Methoxyphenol;Hydroquinone monomethyl ether;HQMME;4-MP
- CAS NO.:150-76-5
- Empirical Formula: C7H8O2
- Molecular Weight: 124.14
- MDL number: MFCD00002332
- EINECS: 205-769-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-05-22 08:50:41
What is 4-Methoxyphenol?
Absorption
The systemic exposure to mequinol was assessed in eight healthy subjects following two weeks of twice-daily topical treatment of a tretinoin and mequinol combination product . About dose of the product corresponding to about 37.3 ug/cm^2 of mequinol was applied to the subjects' backs . The mean Cmax for mequinol was 9.92 ng/mL (range between 4.22 and 23.62 ng/mL) and the Tmax was 2 hours (range between 1 to 2 hours) . The safety of mequinol in this combination formulation is supported by the low systemic exposures of the agent in the subjects .
Toxicity
If a mequinol and tretinoin combination topical product is applied excessively, some potential adverse effects like marked redness, peeling of skin, discomfort, discoloration, or hypopigmentation may occur . Such products are not indicated for oral ingestion .
MSDS data reports that chronic exposure to a dose of 25 UMOL/L in humans can result in mutagenic effects like DNA inhibition in lymphocytes .
The Uses of 4-Methoxyphenol
4-methoxyphenol may be used in the synthesis of butylated hydroxy anisoles via alkylation with methyl tert-butyl ether over a non-zeolitic solid acidic catalyst. This process is eco-friendly when compared to the Friedel-Crafts alkylation reaction. 4-MP may also react with aqueous nitrous acid to form 2-nitro-4-methoxyphenol and benzoquinone in varying ratios depending on the reaction conditions. 4-MP can be used as a building block in designing β-cyclodextrin 4-methoxyphenol conjugates that can be potential ligands for drug complexation.
Background
Mequinol is a phenol used in various applications. It is used as an inhibitor for acrylic monomers and acrylonitirles, as a stabilizer for chlorinated hydrocarbons and ethyl cellulose, as an ultraviolet inhibitor, as a chemical intermediate in the manufacture of antioxidants, pharmaceuticals, plasticizers, and dyestuffs . It is found as an active ingredient in topical drugs used for skin depigmentation indicated for the treatment of solar lentigines.
Indications
Mequinol is currently primarily available only as an active ingredient in combination products combined with tretinoin that are indicated for the treatment of solar lentigines and related hyperpigmented lesions resulting from chronic sun exposure .
Pharmacokinetics
Mequinol is in fact considered a melanocytotoxic chemical which when oxidized in melanocytes results in the formation of toxic entities like quinones . Such cytotoxic compounds subsequently have the potential to damage and destroy pigment cells, therefore causing skin depigmentation . In response, skin cells are naturally capable of protecting themselves against such cytotoxic agents with the help of endogenous intracellular glutathione and the detoxification action of glutathione S-transferase on the cytotoxic compounds . Regardless, it is consequently by way of this seemingly negative and damaging pharmacodynamic profile by which the mechanism of action of mequinol is sometimes described .
Metabolism
Urine samples from melanoma patients treated with mequinol were analyzed and various mequinol metabolites were identified, including 3,4-dihydroxyanisole, the two o-methyl derivatives 3-hydroxy-4-methoxyanisole and 4-hydroxy-3-methoxyanisole, and even hydroquinone which may have originated at least partly from mequinol . All these identified metabolites were excreted predominantly as sulphates and glucuronides - only a small portion of the substances were present in urine in an unconjugated form . Ultimately, the 3,4-dihydroxyanisole is considered the most important metabolite of mequinol .
Properties of 4-Methoxyphenol
Melting point: | 56 °C |
Boiling point: | 243 °C(lit.) |
Density | 1,55 g/cm3 |
Flash point: | >230 °F |
storage temp. | Store below +30°C. |
solubility | Soluble in acetone, ethyl acetate, ethanol, ether, benzene and carbon tetrachloride. |
form | Liquid |
color | Clear colorless to pale yellow |
Water Solubility | 40 g/L (25 ºC) |
Safety information for 4-Methoxyphenol
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral H317:Sensitisation, Skin H319:Serious eye damage/eye irritation H412:Hazardous to the aquatic environment, long-term hazard |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P302+P352:IF ON SKIN: wash with plenty of soap and water. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for 4-Methoxyphenol
InChIKey | NWVVVBRKAWDGAB-UHFFFAOYSA-N |
Abamectin manufacturer
Cefa-Cilinas Biotics Pvt Ltd
JSK Chemicals
Clean Science and Technology Limited
Urmila Chemopharma
S D Fine Chem Limited
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