METHYL 2-HYDROXYBENZOATE
Methyl 2-hydroxybenzoate is a crystalline organic acid with the formula C7H6O3, recognized for its keratolytic, bacteriostatic, and fungicidal properties, making it effective in topical anti-acne products and as an antiseptic.
Methyl 2-hydroxybenzoate is obtained from the bark of white willow and wintergreen leaves, and it plays a significant role in treating wart infections by dehydrating affected skin cells and activating the body's immune response.
Methyl 2-hydroxybenzoate is included in the World Health Organization’s List of Essential Medicines, highlighting its status as a safe and effective treatment within healthcare systems.
CAS Number: 69-72-7
EC Number: 200-712-3
Molecular Formula: C7H6O3
Molecular Weight: 138.12 g/mol
Synonyms: 2-Hydroxybenzoic acid, 2-HYDROXYBENZOIC ACID, ACIDUM SALICYLICUM, ACETYLSALISYLIC ACID IMP C, ACETYLSALICYLIC ACID IMPURITY C, FEMA 3985, SALICYCLIC ACID, SALICYLIC ACID, RETARDER TSA, salicylic acid, 2-Hydroxybenzoic acid, 69-72-7, o-hydroxybenzoic acid, 2-Carboxyphenol, o-Carboxyphenol, Rutranex, Salonil, Retarder W, Duoplant, Keralyt, Psoriacid-S-stift, Freezone, Saligel, Ionil, Salicylic acid soap, Stri-Dex, Verrugon, Salicylic acid collodion,
Benzoic acid, 2-hydroxy-, 2-Hydroxybenzenecarboxylic acid, Phenol-2-carboxylic acid, Orthohydroxybenzoic acid, Acido salicilico, Kyselina salicylova, 2-hydroxy-benzoic acid, CCRIS 6714, HSDB 672, AI3-02407, CHEBI:16914, BRN 0774890, NSC-180, UNII-O414PZ4LPZ, EINECS 200-712-3, O414PZ4LPZ, MFCD00002439, DTXSID7026368, FEMA NO. 3985, CHEMBL424, MLS000069653, DTXCID206368, NSC180, K 537, EC 200-712-3, 29656-58-4, SMR000059163, Acid, Salicylic, ortho-Hydroxybenzoic Acid, o Hydroxybenzoic Acid, 2 Hydroxybenzoic Acid, Acid, o-Hydroxybenzoic, Acid, 2-Hydroxybenzoic, ortho Hydroxybenzoic Acid, Acid, ortho-Hydroxybenzoic, NSC629474, phenol derivative, 7, Salicylic acid (TN), SCHEMBL1967, SALICYLIC ACID [MI], Oprea1_040343, KBioSS_001428, BIDD:ER0602, NCGC00159447-01, NCGC00159447-02, NCGC00159447-04, NCGC00159447-06, NCGC00257065-01, NCGC00259022-01, FT-0645123, FT-0674502, FT-0674503, H0206, H1342, Salicylic Acid Technical Grade, Unichem Salac, 2-Hydroxybenzoic acid, 2-Carboxyphenol, Salicylic acid, 2-HYDROXYBENZOIC ACID,ACIDUM SALICYLICUM, ACETYLSALISYLIC ACID IMP C,ACETYLSALICYLIC ACID IMPURITY C,FEMA 3985,SALICYCLIC ACID,SALICYLIC ACID,RETARDER TSA, Salicylic, Acid,Salicylic, 2 Hydroxybenzoic Acid, Acido Salicilico, Sa - Salicylic Acid, O-Hydroxybenzoic Acid, O Hydroxybenzoic Acid, Salicylic Aci, Acid,2-Hydroxybenzoic, Acidum Salicylicum, O-Carboxyphenol, Salicylic Acid Preparation, Acid,O-Hydroxybenzoic, Kyselina Salicylova, Salicylic Preparation, Acid,Ortho-Hydroxybenzoic, Acido O-Idrossibenzoico, Kyselina 2-Hydroxybenzoova, Caswell No. 731, Benzoic Acid,2-Hydroxy- (10), 2-Carboxyphenol,2-Hydroxybenzenecarboxylate, 2-Hydroxybenzenecarboxylic acid, 2-Hydroxybenzoate, 2-Hydroxybenzoic acid, Benzoic acid, 2-hydroxy-, Benzoic acid, o-hydroxy-, o-Carboxyphenol, o-Hydroxybenzoate, o-Hydroxybenzoic acid, Orthohydroxybenzoic acid, Phenol-2-carboxylate, Phenol-2-carboxylic acid, Psoriacid-S-Stift, Salicyclic acid, Salicylate, Salicylic acid, Saligel, Salonil, Trans-Ver-Sal, 2 Hydroxybenzoic acid Acid, 2-hydroxybenzoic, Acid, salicylic, Acid, O-hydroxybenzoic, Acid, ortho-hydroxybenzoic, O Hydroxybenzoic acid, Ortho hydroxybenzoic acid, Ortho-hydroxybenzoic acid, Advanced pain relief callus removers, Advanced pain relief corn removers, Clear away wart remover, Compound W, Duofil wart remover, Duoplant, Freezone, Ionil, Ionil plus, K 537, K 557, Retarder W, Rutranex, Salicylic acid collodion, Salicylic acid soap, Stri-dex, SA, Benzoic acid, 2-hydroxy-, o-Hydroxybenzoic acid, Phenol-2-carboxylic acid, Psoriacid-S-Stift, Retarder W, Rutranex, Salicylic acid collodion, Salonil, 2-Hydroxybenzoic acid, Acido salicilico, Keralyt, Kyselina 2-hydroxybenzoova, Kyselina salicylova, Orthohydroxybenzoic acid, Duoplant, Freezone, Ionil, Saligel, Compound W, 2-Hydroxybenzenecarboxylic acid, 2-Carboxyphenol, o-Carboxyphenol, Advanced pain relief callus removers, Advanced pain relief corn removers, Clear away wart remover, Dr. Scholl's Callus Removers, Duofil Wart Remover, Ionil plus, Salicylic acid soap, Stri-Dex, Benzoic acid, o-hydroxy-, NSC 180, Trans-Ver-Sal, Domerine, Duofilm, Fostex, Pernox, Salicylic acid & Sulfur Soap, Sebucare, Sebulex, component of Fostex medicated bar and cream, component of Keralyt, Retarder SAX, component of Solarcaine first aid spray, component of Tinver, 7681-06-3, 8052-31-1, Salicyclic acid, Domerine (Salt/Mix), Duofilm (Salt/Mix), Fostex (Salt/Mix), Pernox (Salt/Mix), Salicylic acid & Sulfur Soap (Salt/Mix), Sebucare (Salt/Mix), Sebulex (Salt/Mix), component of Fostex medicated bar and cream (Salt/Mix), component of Keralyt (Salt/Mix), Retarder SAX (Salt/Mix), component of Solarcaine first aid spray (Salt/Mix), component of Tinver (Salt/Mix)
Methyl 2-hydroxybenzoate is an organic compound with the formula HOC6H4COOH.
Methyl 2-hydroxybenzoate has bacteriostatic, fungicidal, and keratolytic actions.
Methyl 2-hydroxybenzoate is odourless and is colourless.
Methyl 2-hydroxybenzoate is a compound obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically.
Methyl 2-hydroxybenzoate has bacteriostatic, fungicidal, and keratolytic actions.
Methyl 2-hydroxybenzoate is a metabolite found in or produced by Escherichia coli
Methyl 2-hydroxybenzoate is a beta hydroxy acid that occurs as a natural compound in plants.
Methyl 2-hydroxybenzoate has direct activity as an anti-inflammatory agent and acts as a topical antibacterial agent due to its ability to promote exfoliation.
Methyl 2-hydroxybenzoate is a compound obtained from the bark of the white willow and wintergreen leaves.
Methyl 2-hydroxybenzoate has bacteriostatic, fungicidal, and keratolytic actions.
A colorless, bitter-tasting solid, Methyl 2-hydroxybenzoate is a precursor to and a metabolite of aspirin (acetylMethyl 2-hydroxybenzoate).
Methyl 2-hydroxybenzoate is a plant hormone, and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen.
The name is from Latin salix for willow tree, from which Methyl 2-hydroxybenzoate was initially identified and derived.
Methyl 2-hydroxybenzoate is an ingredient in some anti-acne products.
Salts and esters of Methyl 2-hydroxybenzoate are known as salicylates.
Methyl 2-hydroxybenzoate is an odorless white to light tan solid.
Methyl 2-hydroxybenzoate sinks and mixes slowly with water.
Methyl 2-hydroxybenzoate is a useful phosphor in the vacuum ultraviolet spectral range, with nearly flat quantum efficiency for wavelengths between 10 and 100 nm.
Methyl 2-hydroxybenzoate fluoresces in the blue at 420 nm.
Methyl 2-hydroxybenzoate is easily prepared on a clean surface by spraying a saturated solution of the salt in methanol followed by evaporation.
Methyl 2-hydroxybenzoate a monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position.
Methyl 2-hydroxybenzoate is obtained from the bark of the white willow and wintergreen leaves.
Methyl 2-hydroxybenzoate has a role as an antiinfective agent, an antifungal agent, a keratolytic drug, an EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor, a plant metabolite, an algal metabolite and a plant hormone.
Methyl 2-hydroxybenzoate is a conjugate acid of a salicylate.
Methyl 2-hydroxybenzoate is lipophilic monohydroxybenzoic acid.
Methyl 2-hydroxybenzoate a type of phenolic acid and a beta-hydroxy acid (BHA).
Beta hydroxy acid is found as a natural compound in plants.
This colourless crystalline organic acid, Methyl 2-hydroxybenzoate, is broadly in use in organic synthesis.
Methyl 2-hydroxybenzoate is derived from the metabolism of salicin.
Methyl 2-hydroxybenzoate is a crystalline organic carboxylic acid and has keratolytic, bacteriostatic and fungicidal properties.
Methyl 2-hydroxybenzoate can be in use as an antiseptic and as a food preservative when consumed in small quantities.
Methyl 2-hydroxybenzoate has a carboxyl group attached to it i.e., COOH.
Methyl 2-hydroxybenzoate is odourless and is colourless.
Methyl 2-hydroxybenzoate is probably known for its use as an important ingredient in topical anti-acne products.
The salts and esters of Methyl 2-hydroxybenzoate are salicylates.
Methyl 2-hydroxybenzoate is on the World Health Organization’s List of Essential Medicines.
Methyl 2-hydroxybenzoate is the safest and most effective medicines needed in a health system.
Methyl 2-hydroxybenzoate, also known as 2-Hydroxybenzoic Acid has the chemical formula C7H6O3.
Methyl 2-hydroxybenzoate appears as an odorless, white-colored to light tan solid with an acrid taste.
Methyl 2-hydroxybenzoate is slightly soluble in Water, therefore, when added to Water, Methyl 2-hydroxybenzoate sinks and slowly mixes with it at ambient conditions.
Methyl 2-hydroxybenzoate is in use in the treatment of wart infections.
The mechanism of Methyl 2-hydroxybenzoate by which professionals treats warts infection is similar to its keratolytic action.
Firstly, Methyl 2-hydroxybenzoate dehydrates the skin cells that are affected by warts and thereby it gradually leads to its shedding off from the body.
Methyl 2-hydroxybenzoate also activates the immune reaction of the body towards the viral wart infection by initiating a mild inflammatory reaction.
Methyl 2-hydroxybenzoate is one of the major components of anti-dandruff shampoos.
Methyl 2-hydroxybenzoate also helps in clearing away the dead and flaky skin cells from your scalp.
Methyl 2-hydroxybenzoate is a monohydroxybenzoic acid, benzoic acid with a hydroxy group in the ortho position.
Methyl 2-hydroxybenzoate is obtained from the bark of white willow and wintergreen leaves.
Methyl 2-hydroxybenzoate has a role as antiinfective agent, antifungal agent, keratolytic drug, EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor, plant metabolite, algal metabolite and plant hormone.
Methyl 2-hydroxybenzoate is the conjugate acid of a salicylate.
Methyl 2-hydroxybenzoate is a component with a structure similar to β-hydroxy acid, which can not only soften the stratum corneum, but also loosen the horn plugs to unclog pores, as well as certain antibacterial and anti-inflammatory effects.
Methyl 2-hydroxybenzoate is not easily soluble in water, but is easily soluble in organic solvents such as ethanol, ether, propanol, and turpentine.
Methyl 2-hydroxybenzoate exists in willow bark, white pearl leaves, and sweet birch in nature, and is the "anti-inflammatory drug" of plants.
Humans have long discovered the medicinal properties of willow plant extracts (natural Methyl 2-hydroxybenzoate).
Ancient Sumerian clay tablets have records of using willow leaves to treat arthritis.
The oldest medical text in ancient Egypt, the Ebers Papyrus, records that the pain-relieving properties of dried willow leaves were known to the Egyptians at least more than 2,000 BC.
The ancient Greek physician Hippocrates documented the medicinal properties of willow bark in the 5th century BC.
This knowledge was repeatedly quoted by famous Greek and Roman physicians such as Galen.
These are ortho-hydroxylated benzoic acids.
Methyl 2-hydroxybenzoate exists in all living species, ranging from bacteria to plants to humans.
Based on a literature review a significant number of articles have been published on Methyl 2-hydroxybenzoate.
Methyl 2-hydroxybenzoate, also called 2-hydrobenzoic or phenolic acid, is a colorless substance in the form of crystals or powder.
Methyl 2-hydroxybenzoate is one of the most commonly used types of hydroxybenzoic acid.
Phenolic acid is highly soluble in polar solvents of organic origin, such as diethyl ether or ethanol, but slightly soluble in water and carbon disulfide.
The density of Methyl 2-hydroxybenzoate is 1.44 g/cm³, melting occurs at 159°C, and boils at 211°C.
The production of Methyl 2-hydroxybenzoate is based on the Kolbe-Schmitt reaction: the carboxylation of sodium phenolate when exposed to carbon dioxide with the creation of the required pressure and temperature for 8-10 hours.
Two grades of the product are produced: A - for the preparation of medicines, B - for other areas of application.
The chemical formula of Methyl 2-hydroxybenzoate is C7H6O3.
Methyl 2-hydroxybenzoate is a natural product extract from Willow bark, well known as an antiinflammatory and antinociceptive agent and a close structural relative to acetylMethyl 2-hydroxybenzoate (aspirin).
Methyl 2-hydroxybenzoate is a ubiquitous plant hormone with many regulatory functions involved in local disease resistance mechanisms and systemic acquired resistance.
The antiinflammatory and antinociceptive effects produced by Methyl 2-hydroxybenzoate and its derivatives in animals are due to inhibition of COX-1 and COX-2 (cyclooxygenase) enzyme activity and suppression of prostaglandin biosynthesis.
Methyl 2-hydroxybenzoate is also of interest as a starting material for the organic synthesis of more elaborate COX suppressors and other chemical structures.
Methyl 2-hydroxybenzoate (from Latin salix, willow tree) is a monohydroxybenzoic acid, a type of phenolic acid and a beta hydroxy acid.
Methyl 2-hydroxybenzoate has the formula C7H6O3.
In an early (1966) biosynthetic process, researchers at Kerr-McGee Oil Industries (now part of Andarko Petroleum) prepared Methyl 2-hydroxybenzoate via the microbial degradation of naphthalene.
Methyl 2-hydroxybenzoate is now commercially biosynthesized from phenylalanine.
AcetylMethyl 2-hydroxybenzoate (aspirin), a prodrug to Methyl 2-hydroxybenzoate, is made by an entirely different process.
Curiously, Methyl 2-hydroxybenzoate is also a metabolite of aspirin.
Methyl 2-hydroxybenzoate and its esters are used as food preservatives, in skin-care products and other cosmetics, and in topical medicines.
Methyl 2-hydroxybenzoate in Signal Transduction:
A number of proteins have been identified that interact with Methyl 2-hydroxybenzoate in plants, especially Methyl 2-hydroxybenzoate binding proteins (SABPs) and the NPR genes (nonexpressor of pathogenesis-related genes), which are putative receptors.
Methyl 2-hydroxybenzoate is an effective inhibitor of COX-2 activity at concentrations far below those required to inhibit NF-κB (20 mg/mL) activation.
Methyl 2-hydroxybenzoate inhibits prostaglandin E2 release when add together with interleukin 1β for 24 hr with an IC50 value of 5 μg/mL, an effect that is independent of NF-κB activation or COX-2 transcription or translation.
Methyl 2-hydroxybenzoate acutely (30 min) also causes a concentration-dependent inhibition of COX-2 activity measured in the presence of 0, 1, or 10 μM exogenous arachidonic acid.
In contrast, when exogenous arachidonic acid is increased to 30 μM, Methyl 2-hydroxybenzoate is a very weak inhibitor of COX-2 activity with an IC50 of >100 μg/mL.
When added together with IL-1β for 24 hr, Methyl 2-hydroxybenzoate causes a concentration-dependent inhibition of PGE2 release with an apparent IC50 value of approximately 5 μg/mL.
The ability of Methyl 2-hydroxybenzoate to directly inhibit COX-2 activity in A549 cells is tested after a 30-min exposure period, followed by the addition of different concentrations of exogenous arachidonic acid (1, 10, and 30 μM).
Methyl 2-hydroxybenzoate causes a concentration-dependent inhibition of COX-2 activity in the absence of added arachidonic acid or in the presence of 1 or 10 μM exogenous substrate with an apparent IC50 value of approximately 5 μg/mL.
However, when the same experiments are performed using 30 μM arachidonic acid, Methyl 2-hydroxybenzoate is an ineffective inhibitor of COX-2 activity, with an apparent IC50 value of more than 100 μg/mL, and achieves a maximal inhibition of less than 50%.
Methyl 2-hydroxybenzoate in Plant Hormone:
Methyl 2-hydroxybenzoate is a phenolic phytohormone, and is found in plants with roles in plant growth and development, photosynthesis, transpiration, and ion uptake and transport.
Methyl 2-hydroxybenzoate is involved in endogenous signaling, mediating plant defense against pathogens.
Methyl 2-hydroxybenzoate plays a role in the resistance to pathogens (i.e. systemic acquired resistance) by inducing the production of pathogenesis-related proteins and other defensive metabolites.
Methyl 2-hydroxybenzoate's defense signaling role is most clearly demonstrated by experiments which do away with it: Delaney et al. 1994, Gaffney et al. 1993, Lawton et al. 1995, and Vernooij et al. 1994 each use Nicotiana tabacum or Arabidopsis expressing nahG, for salicylate hydroxylase.
Pathogen inoculation did not produce the customarily high Methyl 2-hydroxybenzoate levels, SAR was not produced, and no PR genes were expressed in systemic leaves. Indeed, the subjects were more susceptible to virulent – and even normally avirulent – pathogens.
Exogenously, Methyl 2-hydroxybenzoate can aid plant development via enhanced seed germination, bud flowering, and fruit ripening, though too high of a concentration of Methyl 2-hydroxybenzoate can negatively regulate these developmental processes.
The volatile methyl ester of Methyl 2-hydroxybenzoate, methyl salicylate, can also diffuse through the air, facilitating plant-plant communication.
Methyl salicylate is taken up by the stomata of the nearby plant, where it can induce an immune response after being converted back to Methyl 2-hydroxybenzoate.
Uses of Methyl 2-Hydroxybenzoate:
Methyl 2-hydroxybenzoate is used as a food preservative, a bactericide, and an antiseptic.
Methyl 2-hydroxybenzoate is used in the production of other pharmaceuticals, including 4-aminoMethyl 2-hydroxybenzoate, sandulpiride, and landetimide (via salethamide).
Methyl 2-hydroxybenzoate has long been a key starting material for making acetylMethyl 2-hydroxybenzoate (aspirin).
Aspirin (acetylMethyl 2-hydroxybenzoate or ASA) is prepared by the esterification of the phenolic hydroxyl group of Methyl 2-hydroxybenzoate with the acetyl group from acetic anhydride or acetyl chloride.
AcetylMethyl 2-hydroxybenzoate is the standard to which all the other non-steroidal anti-inflammatory drugs (NSAIDs) are compared.
In veterinary medicine, this group of drugs is mainly used for treatment of inflammatory musculoskeletal disorders.
Bismuth subsalicylate, a salt of bismuth and Methyl 2-hydroxybenzoate, "displays anti-inflammatory action (due to Methyl 2-hydroxybenzoate) and also acts as an antacid and mild antibiotic".
Methyl 2-hydroxybenzoate is the active ingredient in stomach-relief aids such as Pepto-Bismol and some formulations of Kaopectate.
Other derivatives include methyl salicylate used as a liniment to soothe joint and muscle pain and choline salicylate used topically to relieve the pain of mouth ulcers.
AminoMethyl 2-hydroxybenzoate is used to induce remission in ulcerative colitis, and has been used as an antitubercular agent often administered in association with isoniazid.
Methyl 2-hydroxybenzoate's salts, the salicylates, are used as analgesics.
Methyl 2-hydroxybenzoate is used in the following products: Fertilizers, cosmetics and personal care products, laboratory chemicals and medicines.
Methyl 2-hydroxybenzoate is used in agriculture, forestry and fisheries, health care and scientific research and development
Methyl 2-hydroxybenzoate is used in machine wash fluids/detergents, automotive care products, paints, coatings or adhesives, fragrances, air fresheners, coolants in refrigerators and oil-based electric heaters.
Methyl 2-hydroxybenzoate is particularly in use in the pharmaceutical industry.
The most common use of Methyl 2-hydroxybenzoate is in the preparation of an analgesic, aspirin, which is an acetylated derivative of Methyl 2-hydroxybenzoate.
Another analgesic formed from it is methyl salicylate, an esterified product of Methyl 2-hydroxybenzoate.
Both of these analgesics are in use to treat headache and other body aches.
Methyl 2-hydroxybenzoate also in use as a mild antiseptic effect known as a bacteriostatic agent.
Methyl 2-hydroxybenzoate does not kill the existing bacteria and hence not an antibacterial agent but prevent the growth of bacteria wherever applied.
Common Uses and Applications of Methyl 2-Hydroxybenzoate: Treatment for various minor skin conditions, Food preservative, Analytic reagent, Industries,Food & Beverage, Pharmaceutical, and R&D/Laboratory.
Methyl 2-hydroxybenzoate is a white solid first isolated from the bark of willow trees (Salix spp.), from which it gets its name.
Methyl 2-hydroxybenzoate is used semiconductors, nanoparticles, photoresists, lubricating oils, UV absorbers, adhesive, leather, cleaner, hair dye, soaps, cosmetics, pain medication, analgesics, antibacterial agent, treatment of dandruff, hyperpigmented skin, tinea pedis, onychomycosis, osteoporosis, beriberi, fungicidal skin disease, autoimmune disease.
In medicine, preparations based on Methyl 2-hydroxybenzoate are used as an antipyretic, antiseptic, antirheumatic and anti-tuberculosis agent, which has an analgesic and anti-inflammatory effect.
These are aspirin, salicylamide, para-aminoMethyl 2-hydroxybenzoate, Lassar paste, preparations for the treatment of corns, ointments, powders.
At food enterprises, Methyl 2-hydroxybenzoate is used as an antiseptic in the manufacture of canned foods.
Methyl 2-hydroxybenzoate is added as a component to cosmetics.
Methyl 2-hydroxybenzoate's antibacterial and exfoliating properties make Methyl 2-hydroxybenzoate possible to soften and remove the keratinized top layer of the skin.
Methyl 2-hydroxybenzoate is used as a reagent and indicator in chemical reactions.
Methyl 2-hydroxybenzoate is used ass a reference standard in salicylate quantification by reverse-phase high-performance liquid chromatography (RP-HPLC).
Both oil of wintergreen and Methyl 2-hydroxybenzoate are widely used as pharmaceuticals.
The manufacture of aspirin from Methyl 2-hydroxybenzoate is of major importance.
Industrially, Methyl 2-hydroxybenzoate is manufactured at high temperature and pressure from the phenol sodium salt and carbon dioxide, with an annual worldwide production of about 50,000 tonnes.
Methyl 2-hydroxybenzoate also occurs as the free acid or its esters in many plant species.
Methyl 2-hydroxybenzoate is obtained as oil of wintergreen by distillation from the leaves of Gaultheria procunbers.
Medicine uses:
Methyl 2-hydroxybenzoate as a medication is commonly used to remove the outer layer of the skin.
As such, Methyl 2-hydroxybenzoate is used to treat warts, psoriasis, acne vulgaris, ringworm, dandruff, and ichthyosis.
Similar to other hydroxy acids, Methyl 2-hydroxybenzoate is an ingredient in many skincare products for the treatment of seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris, acanthosis nigricans, ichthyosis, and warts.
Functions of Methyl 2-Hydroxybenzoate:
Acne treatment, acne treatment:
Methyl 2-hydroxybenzoate is fat-soluble, can penetrate deep into pores to dissolve oil and unclog sebaceous glands.
Methyl 2-hydroxybenzoate's acidity can dissolve hardened oil and keratin, so that the keratin plugs in the hair follicles can be loosened, and Methyl 2-hydroxybenzoate also has mild anti-inflammatory properties.
Conditioning keratin and improving skin photoaging
Methyl 2-hydroxybenzoate has a two-way keratin regulating effect and can remove old keratin, so some patients will experience slight scaling, but this is a manifestation of keratin renewal, and Methyl 2-hydroxybenzoate is not suitable for immature keratinization.
On the contrary, the stratum corneum cells have the effect of promoting keratinization and maturation.
Long-term sunlight exposure can cause skin keratin thickening, skin hypertrophy, skin furrows deepen, skin ridges bulge, forming thick and deep wrinkles, so Methyl 2-hydroxybenzoate can improve skin aging caused by sun exposure.
Anti-inflammatory and bactericidal:
Topical application of Methyl 2-hydroxybenzoate has different degrees of anti-inflammatory, astringent and antipruritic effects on seborrheic dermatitis, papulopustular rosacea, and folliculitis.
The anti-inflammatory effect of aspirin comes from the Methyl 2-hydroxybenzoate formed after being decomposed in the body; and Methyl 2-hydroxybenzoate has a certain broad-spectrum bactericidal ability and is effective against many bacteria and fungi.
Whitening, Eliminate Pigmentation:
Methyl 2-hydroxybenzoate penetrates into pores, dissolves aging keratinocytes, lightens pigmentation and enhances skin cell metabolism.
Methyl 2-hydroxybenzoate can dissolve the connection between the skin cutin, make the cuticle fall off, remove the excessively thick cuticle, promote epidermal metabolism, rejuvenate and whiten the skin, prevent the generation of acne marks, remove the acne marks that have already occurred, and can prevent UV damage and photoaging.
Dietary Sources of Methyl 2-Hydroxybenzoate:
Methyl 2-hydroxybenzoate occurs in plants as free Methyl 2-hydroxybenzoate and its carboxylated esters and phenolic glycosides.
Several studies suggest that humans metabolize Methyl 2-hydroxybenzoate in measurable quantities from these plants.
High-salicylate beverages and foods include beer, coffee, tea, numerous fruits and vegetables, sweet potato, nuts, and olive oil.
Meat, poultry, fish, eggs, dairy products, sugar, breads and cereals have low salicylate content.
Some people with sensitivity to dietary salicylates may have symptoms of allergic reaction, such as bronchial asthma, rhinitis, gastrointestinal disorders, or diarrhea, so may need to adopt a low-salicylate diet.
Experimental Properties of Methyl 2-Hydroxybenzoate:
Physical Properties:
Methyl 2-hydroxybenzoate is a colourless, odourless and needle-shaped crystals at room temperature.
The taste of Methyl 2-hydroxybenzoate is acrid.
The boiling point and melting point of Methyl 2-hydroxybenzoate are 211oC and 315oC respectively.
The Methyl 2-hydroxybenzoate molecule has two hydrogen bond donors and three hydrogen bond acceptors.
The flashpoint of Methyl 2-hydroxybenzoate is 157oC.
Due to Methyl 2-hydroxybenzoate's lipophilic nature, its solubility in water is very poor i.e., 1.8 g/L at 25oC.
Methyl 2-hydroxybenzoate is soluble in organic solvents like carbon tetrachloride, benzene, propanol, ethanol and acetone.
The density ofMethyl 2-hydroxybenzoate is 1.44 at 20oC.
Methyl 2-hydroxybenzoate's vapour pressure is 8.2×105mmHg at 25oC.
Methyl 2-hydroxybenzoate is a tendency to undergo discolouration when exposed to direct sunlight due to its photochemical degradation.
Methyl 2-hydroxybenzoate's heat of combustion is 3.026mj/mole at 25oC.
The pH of a saturated solution of Methyl 2-hydroxybenzoate is 2.4.
Methyl 2-hydroxybenzoate's pka value i.e., dissociation constant is 2.97.
Chemical Properties:
Formation of aspirin:
In the pharmaceutical industry, the most important reaction associated with the use of Methyl 2-hydroxybenzoate is the production of aspirin i.e., acetylMethyl 2-hydroxybenzoate.
Methyl 2-hydroxybenzoate is one of the most commonly used analgesics and blood-thinning agent.
In this reaction, Methyl 2-hydroxybenzoate is reacting with acetic anhydride.
Methyl 2-hydroxybenzoate leads to the acetylation of the hydroxyl group present in the Methyl 2-hydroxybenzoate, thereby resulting in the production of acetylMethyl 2-hydroxybenzoate i.e., aspirin.
Acetic acid is manufactured as a byproduct of this reaction.
This is also present as one of the impurities during large scale production of aspirin.
These impurities must be removed from the resulting product mixture by several refining processes.
Esterification Reaction:
Since Methyl 2-hydroxybenzoate is an organic acid, it undergoes a reaction with organic alcohol groups to produce a new organic chemical class alike ester.
When Methyl 2-hydroxybenzoate is reacting with methanol in an acidic medium preferably sulphuric acid in the presence of heat, a dehydration reaction occurs with the loss of water −OH− ion.
This ion is lost from the carboxylic acid functional group present in the Methyl 2-hydroxybenzoate molecule and the H+ ion is lost from the deprotonation of the methanol molecule, resulting in the formation of methyl salicylate (an ester).
Preparation Methods of Methyl 2-Hydroxybenzoate:
There are two most common methods in use for the preparation of Methyl 2-hydroxybenzoate are as follows:
From Phenol:
When phenol is reacted with sodium hydroxide, Methyl 2-hydroxybenzoate forms sodium phenoxide.
Sodium phenoxide then undergoes distillation and dehydration.
This process is followed by a carboxylation reaction with carbon dioxide, which results in the formation of sodium salicylate i.e., salt of Methyl 2-hydroxybenzoate.
This salt then further reacted with an acid or hydronium ion or any species that denotes a proton to obtain the Methyl 2-hydroxybenzoate.
From Methyl Salicylate:
Methyl salicylate also known as oil of wintergreen is commonly called analgesic in the pharmaceutical industry.
Methyl 2-hydroxybenzoate is in use for the preparation of Methyl 2-hydroxybenzoate.
In this reaction, methyl salicylate is reacted with sodium hydroxide (NaOH) to lead to the formation of a sodium salt intermediate of Methyl 2-hydroxybenzoate.
Methyl 2-hydroxybenzoate is named disodium salicylate, which upon undergoing further reaction with sulphuric acid leads to the formation of Methyl 2-hydroxybenzoate.
Structure of Methyl 2-Hydroxybenzoate:
The structural formula of Methyl 2-hydroxybenzoate is C6H4(OH)COOH.
The chemical formula of Methyl 2-hydroxybenzoate can also be written as C7H6O3 in the condensed form.
The IUPAC name of Methyl 2-hydroxybenzoate is 2-hydroxybenzoic acid.
Methyl 2-hydroxybenzoate has a hydroxyl group i.e., -OH group attached at the ortho position with respect to the carboxylic acid.
This COOH group is present on the benzene ring.
The molecular weight or molar mass of Methyl 2-hydroxybenzoate is 138.12 g/mol.
All carbon atoms present in the benzene ring of Methyl 2-hydroxybenzoate are sp2 hybridized.
Methyl 2-hydroxybenzoate forms an intramolecular hydrogen bond.
In an aqueous solution, Methyl 2-hydroxybenzoate dissociates to lose a proton from the carboxylic acid.
The resulting carboxylate ion i.e., −COO− undergoes intermolecular interaction with the hydrogen atom of the hydroxyl group i.e., -OH.
Methyl 2-hydroxybenzoate leads to the formation of an intramolecular hydrogen bond.
Chemical Synthesis of Methyl 2-Hydroxybenzoate:
Commercial vendors prepare sodium salicylate by treating sodium phenolate (the sodium salt of phenol) with carbon dioxide at high pressure (100 atm) and high temperature (115 °C) – a method known as the Kolbe-Schmitt reaction.
Acidifying the product with sulfuric acid gives Methyl 2-hydroxybenzoate:
At the laboratory scale, Methyl 2-hydroxybenzoate can also be prepared by the hydrolysis of aspirin (acetylMethyl 2-hydroxybenzoate) or methyl salicylate (oil of wintergreen) with a strong acid or base; these reactions reverse those chemicals' commercial syntheses.
Production and Chemical Reactions of Methyl 2-Hydroxybenzoate:
Biosynthesis:
Methyl 2-hydroxybenzoate is biosynthesized from the amino acid phenylalanine.
In Arabidopsis thaliana, Methyl 2-hydroxybenzoate can be synthesized via a phenylalanine-independent pathway.
Reactions:
Upon heating, Methyl 2-hydroxybenzoate converts to phenyl salicylate:
2 HOC6H4CO2H → C6H5O2C6H4OH + CO2 + H2O
Further heating gives xanthone.
Methyl 2-hydroxybenzoate as its conjugate base is a chelating agent, with an affinity for iron(III).
Methyl 2-hydroxybenzoate slowly degrades to phenol and carbon dioxide at 200–230 °C:
C6H4OH(CO2H) → C6H5OH + CO2
Action Mechanism of Methyl 2-Hydroxybenzoate:
Methyl 2-hydroxybenzoate modulates COX-1 enzymatic activity to decrease the formation of pro-inflammatory prostaglandins.
Salicylate may competitively inhibit prostaglandin formation.
Salicylate's antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms.
Methyl 2-hydroxybenzoate, when applied to the skin surface, works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth.
Methyl 2-hydroxybenzoate inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with NADH and noncompetitively with UDPG.
Methyl 2-hydroxybenzoate also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid to the phenolic acceptor.
The wound-healing retardation action of salicylates is probably due mainly to Methyl 2-hydroxybenzoate's inhibitory action on mucopolysaccharide synthesis.
History of Methyl 2-Hydroxybenzoate:
Willow has long been used for medicinal purposes.
Dioscorides, whose writings were highly influential for more than 1,500 years, used 'Itea' (which was possibly a species of willow) as a treatment for 'painful intestinal obstructions,' birth control, for 'those who spit blood,' to remove calluses and corns and, externally, as a 'warm pack for gout.'
William Turner, in 1597, repeated this, saying that willow bark, 'being burnt to ashes, and steeped in vinegar, takes away corns and other like risings in the feet and toes.'
Some of these cures may describe the action of Methyl 2-hydroxybenzoate, which can be derived from the salicin present in willow.
Methyl 2-hydroxybenzoate was used in Europe and China to treat these conditions.
This remedy is mentioned in texts from Ancient Egypt, Sumer, and Assyria.
The Cherokee and other Native Americans use an infusion of the bark for fever and other medicinal purposes.
In 2014, archaeologists identified traces of Methyl 2-hydroxybenzoate on seventh-century pottery fragments found in east-central Colorado.
The Reverend Edward Stone, a vicar from Chipping Norton, Oxfordshire, England, reported in 1763 that the bark of the willow was effective in reducing a fever.
An extract of willow bark, called salicin, after the Latin name for the white willow (Salix alba), was isolated and named by German chemist Johann Andreas Buchner in 1828.
A larger amount of the substance was isolated in 1829 by Henri Leroux, a French pharmacist.
Raffaele Piria, an Italian chemist, was able to convert the substance into a sugar and a second component, which on oxidation becomes Methyl 2-hydroxybenzoate.
Methyl 2-hydroxybenzoate was also isolated from the herb meadowsweet (Filipendula ulmaria, formerly classified as Spiraea ulmaria) by German researchers in 1839.
Methyl 2-hydroxybenzoate's extract causes digestive problems such as gastric irritation, bleeding, diarrhea, and even death when consumed in high doses.
In 1874 the Scottish physician Thomas MacLagan experimented with salicin as a treatment for acute rheumatism, with considerable success, as he reported in The Lancet in 1876.
Meanwhile, German scientists tried sodium salicylate with less success and more severe side effects.
In 1979, salicylates were found to be involved in induced defenses of tobacco against tobacco mosaic virus.
In 1987, Methyl 2-hydroxybenzoate was identified as the long-sought signal that causes thermogenic plants, such as the voodoo lily, Sauromatum guttatum, to produce heat.
Handling and Storage of Methyl 2-Hydroxybenzoate:
Handling:
Use in a well-ventilated area to avoid inhalation of vapors.
Avoid direct contact with skin, eyes, and clothing.
Do not ingest or inhale.
Keep away from heat, sparks, open flames, or other ignition sources.
Storage:
Store in a cool, dry, and well-ventilated area.
Keep container tightly closed when not in use.
Store away from strong acids, oxidizing agents, and strong bases.
Stability and Reactivity of Methyl 2-Hydroxybenzoate:
Stability:
Stable under normal conditions of use and storage.
Reactivity:
May react with strong oxidizers and acids.
Incompatible Materials:
Strong oxidizing agents, strong acids, strong bases.
Hazardous Decomposition Products:
Carbon monoxide (CO), carbon dioxide (CO₂), and irritating fumes may be released during decomposition.
First Aid Measures of Methyl 2-Hydroxybenzoate:
Inhalation:
Move to fresh air immediately.
If breathing is difficult, give oxygen.
Seek medical attention if symptoms persist.
Skin Contact:
Wash with plenty of soap and water for at least 15 minutes.
Remove contaminated clothing.
Seek medical attention if irritation persists.
Eye Contact:
Rinse immediately with plenty of water for at least 15 minutes.
Seek medical attention if irritation develops.
Ingestion:
Do NOT induce vomiting.
Rinse mouth with water.
Seek medical attention immediately.
Firefighting Measures of Methyl 2-Hydroxybenzoate:
Suitable Extinguishing Media:
Use dry chemical, carbon dioxide (CO₂), foam, or water spray.
Special Protective Equipment:
Firefighters should wear self-contained breathing apparatus (SCBA) and full protective clothing.
Hazardous Combustion Products:
Carbon monoxide, carbon dioxide, and irritating vapors may be released.
Firefighting Instructions:
Use water spray to cool containers exposed to fire.
Prevent runoff from entering water sources.
Accidental Release Measures of Methyl 2-Hydroxybenzoate:
Personal Precautions:
Wear appropriate protective equipment (gloves, goggles, and a respirator if necessary).
Avoid inhalation and contact with skin or eyes.
Environmental Precautions:
Prevent material from entering drains, sewers, and waterways.
Cleanup Procedures:
Absorb spilled material with an inert absorbent (e.g., sand or vermiculite).
Collect and place in a suitable, labeled disposal container.
Ventilate the area and wash spill site thoroughly with water.
Exposure Controls/Personal Protection of Methyl 2-Hydroxybenzoate:
Engineering Controls:
Use in a well-ventilated area or under an exhaust hood.
Personal Protective Equipment (PPE):
Respiratory Protection:
Use an approved respirator if exposure limits are exceeded.
Skin Protection:
Wear chemical-resistant gloves.
Eye Protection:
Safety goggles or face shield.
Clothing:
Wear appropriate protective clothing to minimize skin contact.
Hygiene Measures:
Wash hands and exposed skin thoroughly after handling.
Avoid eating, drinking, and smoking in work areas.
Identifiers of Methyl 2-Hydroxybenzoate:
Formula: C7H6O3
Molecular weight: 138,12 g/mol
CAS-No.: 69-72-7
EC-No.: 200-712-3
CAS number: 69-72-7
EC number: 200-712-3
Hill Formula: C₇H₆O₃
Chemical formula: HOC₆H₄COOH
Molar Mass: 138.12 g/mol
HS Code: 2918 21 10
Boiling point: 211 °C (1013 hPa)
Density: 1.44 g/cm3 (20 °C)
Flash point: 157 °C
Ignition temperature: 500 °C
Melting Point: 158 - 160 °C
pH value: 2.4 (H₂O, 20 °C) (saturated solution)
Vapor pressure: 1 hPa (114 °C)
Bulk density: 400 - 500 kg/m3
Solubility: 2 g/l
Chemical formula: C7H6O3
Molar mass: 138.122 g/mol
Appearance: Colorless to white crystals
CAS number: 69-72-7
EC number: 200-712-3
Hill Formula: C₇H₆O₃
Chemical formula: HOC₆H₄COOH
Molar Mass: 138.12 g/mol
HS Code: 2918 21 10
Boiling point: 211 °C (1013 hPa)
Density: 1.44 g/cm3 (20 °C)
Flash point: 157 °C
Ignition temperature: 500 °C
Melting Point: 158 - 160 °C
pH value: 2.4 (H₂O, 20 °C) (saturated solution)
Vapor pressure: 1 hPa (114 °C)
Bulk density: 400 - 500 kg/m3
Solubility: 2 g/l
CAS number: 69-72-7
Weight Average: 138.1207
Monoisotopic: 138.031694058
InChI Key: YGSDEFSMJLZEOE-UHFFFAOYSA-N
Properties of Methyl 2-Hydroxybenzoate:
Physical state: powdercrystalline
Color: white
Odor: odorless
Melting point/freezing point:
Melting point/range: 158 - 160 °C
Initial boiling point and boiling range: 211 °C at 27 hPa
Flammability (solid, gas): No data available
Upper/lower flammability or explosive limits:
Lower explosion limit: 1,1 %(V)
Flash point 157 °C - closed cup
Autoignition temperature: No data available
Decomposition temperature: No data available
pH: 2,4 at 20 °C
Viscosity:
Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Water solubility: No data available
Partition coefficient: n-octanol/water:
log Pow: 2,25 at 25 °C - Bioaccumulation is not expected.
Vapor pressure: 1 hPa at 114 °C
Density: 1,44 g/cm3 at 20 °C
Relative density: No data available
Relative vapor density: No data available
Particle characteristics: No data available
Explosive properties: No data available
Oxidizing properties: none
Other safety information: No data available
Chemical Name : 2 – Hydroxybenzoic Acid
Molecular Formula : C7H6O3
Molecular Weight : 138.1
Description : White / colourless, crystalline powder / acicular crystals
Molecular Weight: 138.12 g/mol
XLogP3: 2.3
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Rotatable Bond Count: 1
Exact Mass: 138.031694049 g/mol
Monoisotopic Mass: 138.031694049 g/mol
Topological Polar Surface Area: 57.5Ų
Heavy Atom Count: 10
Complexity: 133
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Odor: Odorless
Density: 1.443 g/cm3 (20 °C)
Melting point: 158.6 °C (317.5 °F; 431.8 K)
Boiling point: 211 °C (412 °F; 484 K) at 20 mmHg
Sublimation conditions: Sublimes at 76 °C
Solubility in water:
1.24 g/L (0 °C)
2.48 g/L (25 °C)
4.14 g/L (40 °C)
17.41 g/L (75 °C)
77.79 g/L (100 °C)
Solubility: Soluble in ether, CCl4, benzene, propanol,
acetone, ethanol, oil of turpentine, toluene
Solubility in benzene:
0.46 g/100 g (11.7 °C)
0.775 g/100 g (25 °C)
0.991 g/100 g (30.5 °C)
2.38 g/100 g (49.4 °C)
4.4 g/100 g (64.2 °C)
Thermochemistry of Methyl 2-Hydroxybenzoate:
Std enthalpy of formation (ΔfH⦵298): −589.9 kJ/mol
Std enthalpy of combustion (ΔcH⦵298): -3.025 MJ/mol
