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Mequinol
Mequinol
Mequinol
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Mequinol
Clinical data
Other names4-Hydroxyanisole; para-Guaiacol
AHFS/Drugs.comInternational Drug Names
MedlinePlusa682437
Routes of
administration		Topical
ATC code
Legal status
Legal status
  • CA: Unscheduled
  • US: ℞-only and Unscheduled
  • In general: unscheduled
Identifiers
  • 4-Methoxyphenol
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.005.246 Edit this at Wikidata
Chemical and physical data
FormulaC7H8O2
Molar mass124.139 g·mol−1
Density1.55 g/cm3
Melting point52.5 °C (126.5 °F)
Boiling point243 °C (469 °F)
  • InChI=1S/C7H8O2/c1-9-7-4-2-6(8)3-5-7/h2-5,8H,1H3 checkY
  • Key:NWVVVBRKAWDGAB-UHFFFAOYSA-N checkY
  (verify)

Mequinol, MeHQ or 4-methoxyphenol, is an organic compound with the formula CH3OC6H4OH. It is a phenol with a methoxy group in the para position. A colorless solid, it is used in dermatology[1] and organic chemistry.[2]

Use in dermatology

[edit]

Mequinol is a common active ingredient in topical drugs used for skin depigmentation. As a topical drug mequinol is often mixed with tretinoin, a topical retinoid. A common formulation for this drug is an ethanolic solution of 2% mequinol and 0.01% tretinoin by mass.[1] Dermatologists commonly prescribe the drug to treat liver spots.

Lower dosages of mequinol have been used in conjunction with a Q-switched laser to depigment skin in patients with disseminated idiopathic vitiligo.[3]

Organic chemistry

[edit]

In organic chemistry 4-methoxyphenol is used as a polymerisation inhibitor (e.g. acrylates or styrene monomers).[2]

4-Methoxyphenol can be produced from p-benzoquinone and methanol via a free radical reaction.[4][5]

Safety

[edit]

The U.S. National Institute for Occupational Safety and Health (NIOSH) has set a recommended exposure limit (REL) of 5 mg/m3 over an 8-hour workday.[6]

See also

[edit]

References

[edit]
[edit]
Revisions and contributorsEdit on WikipediaRead on Wikipedia

Mequinol

View on Grokipedia
from Grokipedia
Mequinol, also known as 4-methoxyphenol or p-methoxyphenol, is an organic compound with the molecular formula C₇H₈O₂ that serves as a topical depigmenting agent in dermatological treatments. It functions primarily as a tyrosinase inhibitor, blocking melanin formation by competing with melanin precursors and forming toxic quinones that damage melanocytes, thereby lightening hyperpigmented skin areas. In clinical use, mequinol is most commonly formulated at a 2% concentration in combination with 0.01% tretinoin, enhancing depigmentation through synergistic effects on skin cell proliferation and pigmentation regulation. This combination product, originally marketed as Solagé, was approved by the U.S. (FDA) on December 10, 1999, for the treatment of solar lentigines—flat, brown spots caused by chronic sun exposure—as an adjunct to comprehensive and sun avoidance programs. It is applied topically twice daily to affected areas, with visible improvements typically observed after 4 to 24 weeks of consistent use, though it is not indicated for conditions like or post-inflammatory . The brand Solagé was discontinued in the United States in 2010, and as of 2025, generic versions of the mequinol-tretinoin combination are no longer commercially available. Common side effects include transient skin irritation, redness, dryness, and peeling, often exacerbated by sun exposure, necessitating strict photoprotection during treatment. Contraindications include (FDA X in combination due to tretinoin risks) and hypersensitivity to ingredients, with caution advised for patients with or compromised skin barriers. Clinical trials have demonstrated its efficacy in reducing solar lentigines with a favorable safety profile when used as directed, positioning it as a targeted option for photoaging-related .

Chemical Properties

Molecular Structure

Mequinol has the molecular formula C7H8O2C_7H_8O_2, consisting of a ring substituted with oxygen-containing functional groups. Its IUPAC name is 4-methoxyphenol, with common alternative names including mequinol, 4-hydroxyanisole, and p-methoxyphenol. Structurally, mequinol features a phenolic hydroxyl group (−OH-OH) attached to carbon 1 of the ring and a (−OCH3-OCH_3) at the para position (carbon 4), resulting in a planar aromatic system with the oxygen atoms oriented to facilitate hydrogen bonding and potential effects. This compound is a derivative of (1,4-dihydroxy), where one hydroxyl group is replaced by a , which modifies its electrophilic reactivity compared to the parent .

Physical and Chemical Characteristics

Mequinol, or 4-methoxyphenol, appears as a white to off-white crystalline or waxy solid with a characteristic phenolic odor. Its is 124.14 g/mol. The compound has a ranging from 52 to 57 °C and a of 243 °C at standard . Its is 1.55 g/cm³ at 20 °C. Mequinol exhibits low in , approximately 20–40 g/L at 25 °C, but is highly soluble in organic solvents such as alcohols, ethers, acetone, and . Chemically, mequinol is stable under normal storage conditions but is sensitive to oxidation in air and reacts with strong oxidants, acids, and bases; it functions as a free radical scavenger, commonly used as a inhibitor. In spectroscopic analysis, mequinol shows absorption maxima at 224 nm (log ε = 3.85), 288 nm (log ε = 3.50), and 298 nm (log ε = 3.37) in . reveals a characteristic broad phenolic O-H stretch around 3300–3500 cm⁻¹, along with aromatic C=C stretches near 1500–1600 cm⁻¹.

Synthesis and Production

Mequinol, or 4-methoxyphenol, is primarily synthesized through the selective mono-methylation of using , often facilitated by p-benzoquinone as a catalyst in a process. This method yields mequinol as a key product or byproduct during production, where p-benzoquinone serves both as an oxidant and catalyst to promote regioselective etherification. The reaction typically involves refluxing a 1:1 molar mixture of and p-benzoquinone in with a catalytic amount of at approximately 64°C, achieving quantitative yields of mequinol within 20-30 minutes. The simplified key reaction equation is: \ceC6H4O2+CH3OH−>CH3OC6H4OH\ce{C6H4O2 + CH3OH -> CH3OC6H4OH} where p-benzoquinone (C₆H₄O₂) reacts with methanol to form mequinol (CH₃OC₆H₄OH), though in practice, is regenerated to drive selectivity. Alternative laboratory routes include direct methylation of using or methyl iodide under basic conditions, such as with in at 25°C, which provides good for the mono-methylated product. Another approach is the of 4-methoxychlorobenzene (1-chloro-4-methoxybenzene) via palladium-catalyzed with , offering a viable pathway from precursors under milder conditions than traditional high-pressure . In industrial production, large-scale synthesis often employs continuous liquid-phase reactions of and over catalysts like silica-alumina or zeolites at 200-350°C and 0.5-10 MPa, with methanol-to-hydroquinone molar ratios of 3-30, enabling high conversion and selectivity. Purification is achieved through under reduced pressure or recrystallization from solvents like , ensuring high purity for applications. Typical yields range from 70-90%, while optimize for scalability with comparable efficiencies.

Medical Uses

Dermatological Indications

Mequinol is primarily indicated for the treatment of solar lentigines, commonly known as age spots or liver spots, on the face and dorsal hands as part of a comprehensive and sun avoidance program. It is approved solely in combination with tretinoin and has no standalone regulatory approval for dermatological use. The standard is a topical solution containing 2% mequinol and 0.01% tretinoin, applied twice daily (morning and evening, at least 8 hours apart) directly to the using an applicator tip, with treatment durations up to 24 weeks to achieve visible improvement. The branded product Solagé was discontinued in 2010, though generic equivalents may be available in some markets. Clinical trials, including two double-blind, multicenter phase III studies, demonstrated statistically significant improvements in appearance compared to individual components or controls, with rates ranging from 52.6% to over 80%, particularly for facial after 12 weeks of use. This treatment is most suitable for fair-skinned (Caucasian) individuals over 50 years of age with sun-damaged skin, as and have not been adequately established in non-Caucasians or pediatric patients. Off-label applications include the management of other disorders, such as , where a case series in men reported complete clearance in 80% of patients after 12 weeks of twice-daily application.

Mechanism of Action

Mequinol primarily exerts its depigmenting effects through of , the rate-limiting enzyme in the melanin biosynthesis pathway. As a phenolic derivative, it binds to the of , acting as an alternative substrate that competes with L-tyrosine. This interaction prevents the enzymatic oxidation of L-tyrosine to and the subsequent formation of dopaquinone, thereby disrupting the initial steps of melanogenesis and reducing overall production. Mequinol also forms toxic quinones that damage melanocytes, selectively reducing pigmentation without widespread to other skin cells. Biochemically, the process can be represented as forming an inhibited complex with mequinol, halting the required for precursor synthesis. This targeted enzymatic blockade leads to decreased synthesis in hyperactive melanocytes, promoting a gradual reduction in pigmentation. At the cellular level, mequinol further diminishes the transfer of melanosomes—pigment-containing organelles—from melanocytes to , which contributes to the visible lightening of hyperpigmented patches. These effects manifest over 4-12 weeks of consistent topical application, resulting in lighter in treated areas. In comparison to , mequinol provides more potent with reduced irritation potential, making it suitable for longer-term use in dermatological applications.

Combination Therapies

Mequinol is most commonly formulated in combination with tretinoin for topical treatment of disorders, providing synergistic effects where tretinoin enhances epidermal turnover to facilitate mequinol's penetration and action. The standard approved product, Solagé (2% mequinol and 0.01% tretinoin), received FDA approval in 1999 as an adjunct to sun avoidance programs for solar lentigines. The branded product Solagé was discontinued in 2010, though generic equivalents may be available in some markets. This combination leverages mequinol's inhibition with tretinoin's keratolytic properties to achieve greater lesion lightening than either agent alone. The recommended application protocol involves applying the solution twice daily—once in the morning and once in the evening, at least eight hours apart—to affected areas using the applicator tip, while avoiding normal skin and mucous membranes. Treatment should be accompanied by broad-spectrum (SPF 30 or higher) due to increased , with visible improvement typically occurring over 3 to 6 months of continuous use; full effects may take up to 24 weeks, after which maintenance therapy can be considered to prevent recurrence. In clinical trials, this regimen resulted in moderate or greater improvement in 57% of facial solar lentigines, with 3% achieving complete clearing, outperforming 3% monotherapy in pigmentation reduction. For management, particularly in extensive cases requiring , mequinol has been combined with Q-switched therapy to accelerate uniform pigment removal, enhancing outcomes in recalcitrant lesions. Combinations with antioxidants are under exploration to bolster mequinol's inherent properties, potentially mitigating post-treatment rebound through stabilized formulations. Efficacy data from pivotal studies indicate that mequinol-tretinoin combinations achieve clinical success rates of 52.6% to over 80% in lesion clearance for solar lentigines, significantly higher than the approximately 40% seen with select monotherapies like alone. These improved outcomes, coupled with rising demand for cosmetic variants, are projected to drive the global mequinol market to $230 million by 2032. In the United States, mequinol-tretinoin combinations like Solagé remain prescription-only due to regulatory oversight on efficacy and safety. Lower-concentration mequinol formulations (e.g., 2%) are available over-the-counter in some regions as bleaching creams, though availability varies by country and requires verification of local regulations.

Pharmacology and Pharmacokinetics

Absorption and Distribution

Mequinol, when applied topically as a 2% solution often in with 0.01% tretinoin (as in Solagé), exhibits low systemic absorption, with mean peak plasma concentrations (Cmax) of approximately 10 ng/mL and an area under the curve (AUC0-12h) of 33 ng·h/mL following twice-daily application to 400 cm² of for 14 days in healthy volunteers. This limited penetration—estimated indirectly through low plasma exposure—results in primarily local effects at the application site, with minimal entry into the bloodstream due to its lipophilic nature and molecular weight, which favor barrier interaction over deep systemic uptake. In vitro studies using in Franz diffusion cells demonstrate rapid of mequinol, with 40% penetrating through the skin by 24 hours and 60% by 72 hours, yet less than 1% of the applied dose is retained in the or at 72 hours, indicating quick transit through layers without substantial accumulation. Distribution is thus confined largely to the site of application, with any absorbed mequinol dispersing throughout total at low concentrations, as suggested by its consistent with extracellular and intracellular fluid equilibration, though overall systemic levels remain negligible. Absorption is enhanced by co-application with tretinoin, which improves penetration of mequinol through increased epidermal turnover and barrier modulation. No significant tissue accumulation occurs with repeated dosing, as plasma levels stabilize without elevation beyond initial exposure. Locally in the skin, mequinol clears rapidly, aligning with a systemic elimination of 30–90 minutes observed in studies, supporting its transient presence in dermal layers.

Metabolism and Excretion

Mequinol undergoes hepatic primarily through phase II conjugation reactions, forming and conjugates of its metabolites. The major involves oxidation to 3,4-dihydroxyanisole, followed by conjugation, with minor contributions from ring leading to isomers such as 3-hydroxy-4-methoxyanisole and 4-hydroxy-3-methoxyanisole, as well as . These oxidative steps play a limited role compared to conjugation, which predominates in systemic processing. Excretion of mequinol occurs mainly via the renal route, with conjugates representing the primary form eliminated in ; unconjugated metabolites constitute only a small fraction. Fecal elimination is negligible, and the majority of absorbed mequinol is cleared as these conjugated products. Systemic exposure remains low following topical application due to limited percutaneous absorption and subsequent first-pass metabolism in the liver, with no active metabolites identified that contribute to its pharmacological effects.

Drug Interactions

Mequinol, particularly when combined with tretinoin in topical formulations, can interact with photosensitizing agents, increasing the risk of sunburn and skin damage due to enhanced . Concomitant use with certain antibiotics such as tetracyclines, sulfa drugs, or phenothiazines like may amplify this effect, as these agents independently heighten UV sensitivity. Nonsteroidal anti-inflammatory drugs (NSAIDs) with photosensitizing properties, such as , should also be used cautiously to avoid exacerbated . Topical interactions primarily involve additive skin irritation when mequinol is co-applied with other exfoliating or drying agents beyond its approved combination with tretinoin. Concurrent use with additional retinoids can lead to excessive , peeling, and discomfort, necessitating avoidance or careful spacing of applications. Similarly, hydroquinone-containing products may cause compounded irritation and should not be used simultaneously on the same area. Systemic drug interactions with mequinol are minimal owing to its low absorption, limiting potential for widespread metabolic interference. Diuretics with photosensitizing effects, such as hydrochlorothiazide, warrant monitoring for heightened reactions. Cosmetic products that enhance penetration, such as exfoliants (e.g., those containing or alpha-hydroxy acids) or high-alcohol formulations, can increase local exposure to mequinol, potentially elevating irritation and efficacy risks. Astringents, spices, or lime-based products may induce transient stinging or burning upon co-application. To manage these interactions, applications of interacting topicals or should be spaced apart, ideally by several hours, and patients should monitor for signs of or excessive dryness with concurrent therapies. The approved synergy with tretinoin in combination products remains a key therapeutic approach without additional interaction concerns when used as directed.

Safety and Toxicology

Adverse Effects

The most common adverse effects of mequinol, particularly when used topically in combination with tretinoin as in Solagé, are local skin reactions. These include (redness) occurring in approximately 49% of patients, burning, stinging, or tingling sensations in 26%, (peeling or dryness) in 14%, and pruritus (itching) in 12%. irritation is reported in about 5% of cases. These reactions are typically mild to moderate in severity, with 66% of affected patients experiencing mild symptoms and 30% moderate ones, often appearing within the first 8 weeks of treatment. Transient , including halo hypopigmentation around treated lesions, affects 4-6% of users, primarily at the application site or surrounding . In most instances (89%), this resolves after discontinuation of treatment, though a small percentage (2.8%) may persist beyond 120 days. has been noted in sensitive individuals, manifesting as rash or , though it is uncommon. Systemic adverse effects are rare due to minimal absorption of mequinol, with peak plasma concentrations below 10 ng/mL. Reported instances include or , occurring in less than 1% of users, typically only with excessive application. Long-term have shown no evidence of carcinogenicity at doses up to 80 mg/kg. Overall, adverse effects are mostly self-limiting and resolve upon discontinuation, with only about 6% of patients discontinuing due to cutaneous reactions. Severity may increase with sun exposure, exacerbating and . Weekly skin checks are recommended during the first month of use to monitor for emerging reactions.

Contraindications and Precautions

Mequinol is contraindicated in patients with a known to mequinol, tretinoin, or any other components of the formulation. As a phenolic derivative, it should also be avoided in individuals with to due to potential . The combination product with tretinoin is classified as FDA X and is contraindicated during pregnancy, as it may cause fetal harm based on animal studies showing teratogenic effects, with risks outweighing any benefits for treating solar lentigines. Precautions are advised for several patient groups and conditions. Use during is not recommended due to limited data on into ; if necessary, apply to the smallest area for the shortest duration and avoid the or . Safety and efficacy have not been established in pediatric patients, particularly those under 12 years, and mequinol is not indicated for this population. It should be avoided on with active infections, , or compromised , such as eczema or open wounds, to prevent exacerbation. Sun protection is essential during treatment, as mequinol increases ; patients must avoid or minimize exposure to , sunlamps, or UV sources and use broad-spectrum with SPF 15 or higher along with protective clothing. Discontinue use if severe irritation, such as marked , burning, or peeling, develops. In special populations, caution is warranted for elderly patients due to potentially thinner , which may heighten irritation risk, although no specific age-related differences in safety were observed in studies. For individuals with darker skin tones (Fitzpatrick Skin Type VI), safety and efficacy are not established, and there is an increased risk of , particularly in those with . Treatment should be discontinued if there is no improvement in pigmentation after 3 months or if worsens, with repigmentation possible upon cessation.

Regulatory Status

In the United States, mequinol received approval from the (FDA) in 1999 as a component of the prescription combination product Solagé (mequinol 2% and tretinoin 0.01% topical solution) for the treatment of solar lentigines. This approval classifies the product as a prescription-only , while mequinol itself is unscheduled and not subject to controlled substance regulations for non-medical applications. However, the Cosmetic Ingredient Review (CIR) Expert Panel deemed p-hydroxyanisole (mequinol) unsafe for use in cosmetics in 1985 due to its potential for dermal , , and , limiting its standalone cosmetic availability. In the and internationally, mequinol is permitted as a cosmetic ingredient without specific restrictions listed in Annex III of Regulation (EC) No 1223/2009, provided it complies with general safety requirements for cosmetic products; concentrations up to 2% are commonly used in leave-on formulations for pharmaceutical or purposes under prescription guidance. For medicinal uses, it remains classified as a prescription agent in pharmaceutical combinations. Mequinol is not a under international drug scheduling frameworks. As of 2025, there have been no major regulatory changes to mequinol's status globally. The National Institute for Occupational Safety and Health (NIOSH) maintains a of 5 mg/m³ as a time-weighted average over an 8- or 10-hour workday for occupational settings. Additionally, mequinol holds (GRAS) status for use as an indirect in components of paper and paperboard intended for contact with aqueous and fatty foods, per 21 CFR 176.170. Labeling requirements for mequinol-containing products mandate warnings about sun protection, including instructions to avoid sun exposure, use protective clothing, and apply broad-spectrum with SPF 15 or higher, due to increased risks; these are explicitly required for prescription formulations like Solagé.

History and Market

Development and Approval

Mequinol, chemically known as 4-methoxyphenol, was first identified as a of phenol during 19th-century chemical explorations of aromatic compounds. Initially, in the mid-20th century, it found industrial application as a polymerization inhibitor for vinyl monomers such as acrylates and styrenes, leveraging its properties to prevent unwanted radical reactions during storage and processing. Medical interest in mequinol emerged in the , driven by research into its depigmenting potential through inhibition of , the key enzyme in synthesis. Pivotal clinical development focused on its combination with tretinoin, with applications submitted to the FDA in 1997 for the treatment of solar lentigines. This led to two multicenter, double-blind, randomized controlled trials conducted between 1997 and 1998, involving over 500 patients, which demonstrated significant improvement in hyperpigmented lesions compared to vehicle controls. These trials confirmed the efficacy and safety of the 2% mequinol/0.01% tretinoin formulation, paving the way for FDA approval of Solagé on December 10, 1999, as a topical solution for solar lentigines. Post-approval studies expanded exploration of mequinol's applications, including its potential in management through selective , with a 2000 study evaluating its use for in universalis. The original for the mequinol-tretinoin combination (US 5,194,247) expired on March 16, 2010, facilitating the development and market entry of generic versions. Prior to 2020, clinical data on mequinol use in pediatric populations remained limited, with product labeling consistently noting that safety and efficacy had not been established in children, based on the absence of dedicated trials in this group. Subsequent safety reviews, including updated FDA assessments through 2019, reiterated these gaps while emphasizing precautions for off-label use in younger patients. Mequinol is primarily available by prescription and the as a 2% topical solution, often combined with 0.01% tretinoin for treating solar lentigines and disorders. The original brand Solagé (mequinol 2%/tretinoin 0.01%) was discontinued by its manufacturer in 2010, but generic equivalents continue to be accessible through pharmacies and clinics as of 2025. In regions like , where the market is rapidly expanding due to rising demand for skin lightening products, mequinol appears in lower concentrations within cosmetic formulations, though over-the-counter access remains limited by regulatory similarities to restrictions. As of 2023, the global mequinol market was valued at USD 150 million and is projected to reach USD 230 million by 2032, reflecting a (CAGR) of approximately 4.9%. This growth is primarily driven by increasing consumer demand for anti-aging and treatments amid rising awareness of skin health and disposable incomes in urban populations. holds the largest market share, while is the fastest-growing region with a CAGR of 6.1%, fueled by and beauty consciousness in countries like , , and . Recent trends emphasize advancements in topical formulations, including more stable and targeted delivery systems to enhance efficacy and reduce irritation. There is also a shift toward sustainable production methods, such as greener synthesis processes and improved to minimize environmental impact from chemical manufacturing. Influences from K-beauty have contributed to its integration into multifunctional serums focused on even skin tone and personalization. Key challenges include stringent regulatory hurdles in the and concerns related to long-term use, alongside from alternatives like , which offer similar tyrosinase-inhibiting effects with perceived lower risks. dependencies on the further complicate availability, particularly for high-purity grades. Looking ahead, the market is poised for expansion in emerging economies across and , supported by R&D into hybrid products combining mequinol with peptides for enhanced anti-aging benefits. Ongoing collaborations aim to develop innovative applications, potentially broadening its role beyond traditional .

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