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2-Hydroxybenzoic acid is an important organic synthetic raw material, widely used in medicine, pesticides, dyes, rubber, food and perfumes.
In the pharmaceutical industry, the main drug productions of 2-Hydroxybenzoic acid are sodium salicylate, wintergreen oil (methyl salicylate), aspirin (acetylsalicylic acid), salicylic acid amine, phenyl salicylate.
In dye industry, 2-Hydroxybenzoic acid is used for production mordant pure yellow , direct yellow 3GN, direct yellow GR, direct brown 3GN, acid mordant brown G, acid mordant yellow GG, acid yellow dye complex.
CAS: 69-72-7
MF: C7H6O3
MW: 138.12
EINECS: 200-712-3
Synonyms
ACIDUM SALICYLICUM;ACETYLSALICYLIC ACID IMPURITY C;SALICYLIC ACID;RETARDER TSA;RETARDER W;RARECHEM AL BO 0194;2-Carboxyphenol;Liposomal Salicylic Acid,Water-Soluble Supramolecular Salicylic Acid
In pesticide production, 2-Hydroxybenzoic acid is used for the synthesis of organic phosphorus pesticide Isocarbophos, intermediate isopropyl salicylate isofenphos methyl and Rodenticide warfarin, coumatetralyl intermediate 4-hydroxycoumarin.
In rubber industry, 2-Hydroxybenzoic acid is used as anti scorching agent and production of ultraviolet absorbent and foaming agent.
2-Hydroxybenzoic acid is perfume material, used for the preparation of methyl salicylate, salicylic acid ethyl ester; food preservatives, its sodium Salt is mostly used, now a number of countries have been banned; methyl salicylate can be used as oral cleaning agents, such as toothpaste flavor.
2-Hydroxybenzoic acid is a mono hydroxy benzoic acid, a type of phenolic acid and a beta hydroxy acid.
This colorless crystalline organic acid is widely used in organic synthesis and functions as a plant hormone.
2-Hydroxybenzoic acid is derived from the metabolism of salicin.
In addition to being an important active metabolite of aspirin (acetylsalicylic acid), which acts in part as a prod rug to salicylic acid, it is probably best known for its use in anti-acne treatments.
The salts and esters of 2-Hydroxybenzoic acid are known as salicylates.
A monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position.
2-Hydroxybenzoic acid is obtained from the bark of the white willow and wintergreen leaves.
A crystalline aromatic carboxylic acid.
2-Hydroxybenzoic acid is used in medicines, as an antiseptic, and in the manufacture of azo dyes.
2-Hydroxybenzoic acid's ethanoyl (acetyl) ester is aspirin.
2-Hydroxybenzoic acid is an organic compound with the formula C7H6O3.
A colorless (or white), bitter-tasting solid, it is a precursor to and a metabolite of acetylsalicylic acid (aspirin).
2-Hydroxybenzoic acid is a plant hormone, and the name is from Latin salix for willow tree, from which it was initially identified and derived.
2-Hydroxybenzoic acid is used as an ingredient in dermatologic cosmetics (e.g. anti-acne products).
Salts and esters of 2-Hydroxybenzoic acid are known as salicylates.
In the USA, 2-Hydroxybenzoic acid has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen.
2-Hydroxybenzoic acid Chemical Properties
Melting point: 158-161 °C(lit.)
Boiling point: 211 °C(lit.)
density: 1.44
bulk density: 400-500kg/m3
vapor density: 4.8 (vs air)
vapor pressure: 1 mm Hg ( 114 °C)
refractive index: 1,565
FEMA: 3985 | 2-HYDROXYBENZOIC ACID
Fp: 157 °C
storage temp.: 2-8°C
solubility: ethanol: 1 M at 20 °C, clear, colorless
pka: 2.98(at 25℃)
form: Solid
color: White to off-white
PH Range: Non0 uorescence (2.5) to dark blue 0 uorescence (4.0)
Odor: at 100.00 %. faint phenolic nutty
PH: 3.21(1 mM solution);2.57(10 mM solution);2.02(100 mM solution);
Odor Type: nutty
biological source: synthetic
Water Solubility: 1.8 g/L (20 ºC)
Sensitive: Light Sensitive
λmax: 210nm, 234nm, 303nm
Merck: 14,8332
JECFA Number: 958
Sublimation: 70 ºC
BRN: 774890
Henry's Law Constant: 1.3×103 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Stability: Stable. Substances to be avoided include oxidizing agents, strong bases, iodine, fluorine. Combustible. Sensitive to light.
Major Application: 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
InChI: 1S/C7H6O3/c8-6-4-2-1-3-5(6)7(9)10/h1-4,8H,(H,9,10)
InChIKey: YGSDEFSMJLZEOE-UHFFFAOYSA-N
LogP: 2.01
CAS DataBase Reference: 69-72-7(CAS DataBase Reference)
NIST Chemistry Reference: Benzoic acid, 2-hydroxy-(69-72-7)
EPA Substance Registry System: 2-Hydroxybenzoic acid (69-72-7)
2-Hydroxybenzoic acid is a white powder with an acrid taste that is stable in air but gradually discolored by light.
Soluble in acetone, oil of turpentine, alcohol, ether,benzene; slightly soluble in water,and combustible.
Derived by reacting a hot solution of sodium phenolate with carbon dioxide and acidifying the sodium salt thus formed.
Used in the manufacture of aspirin and salicylates, resins, dyestuff intermediate, prevulcanization inhibitor, analytical reagent,and fungicide.
2-Hydroxybenzoic acid has the formula C6H4(OH) COOH, where the OH group is ortho to the carboxyl group.
2-Hydroxybenzoic acid is also known as 2- hydroxybenzoic acid.
2-Hydroxybenzoic acid is poorly soluble in water (2 g / L at 20 °C).
2-Hydroxybenzoic acid can be prepared by the esterification of the phenolic hydroxyl group of salicylic acid with the acetyl group from acetic anhydride or acetyl chloride.
Physical properties
Appearance: white crystalline powder.
Solubility: Absolutely soluble in ethanol, soluble in ether and chloroform, slightly soluble in water and anhydrous ether.
Stability: Stable at room temperature, discomposes into phenol and carbon dioxide after rapidly heated.
2-Hydroxybenzoic acid’s partially acidic.
Aspirin. Appearance: white crystal and decomposes at 136–140 °C.
Melting point: 136°C.
2-Hydroxybenzoic acid is the acetyl derivative of salicylic acid with weak acidity.
2-Hydroxybenzoic acid's acidity coefficient is 3.5 at 25°C.
Stability: 2-Hydroxybenzoic acid decomposes rapidly in ammonium acetate, alkali metal of acetate, carbonate, citrate or hydroxide solutions.
There are two crystal forms of aspirin including crystal form I and II.
2-Hydroxybenzoic acid has sterilization ability, 2.5% alcohol solution (called spiritus) is used as a topical medicine in the treatment of tinea manus and tinea pedis, also can be made into ointment.
2-Hydroxybenzoic acid can be used for food preservative or preservatives, also can be used for the preparation of toothpaste, mouthwash.
2-Hydroxybenzoic acid has antipyretic and analgesic effects, can cure rheumatism and so on.
2-Hydroxybenzoic acid's all esters can be used as drug and spices.
2-Hydroxybenzoic acid has pleasant aromas of holly, is used for the preparation of perfume and soap flavor.
2-Hydroxybenzoic acid is coated on the skin, can penetrate into the muscle and let out of salicylic acid to release local pain, so it also can be used for the treatment of pain, contusion, sprain and other medication.
2-Hydroxybenzoic acid has orchid aroma, benzyl salicylate has weak ester aroma, both can prepare perfume or soap flavor.
The common name of phenyl salicylate is Salo, was hydrolyzed into phenol and salicylic acid in the intestine , is a kind of effective enteral preservatives.
Another Kind drug related to 2-Hydroxybenzoic acid is para aminosalicylic acid (PAS, see "Para amino salicylic acid), Its sodium and calcium salts are used as anti TB drugs for acute exudative pulmonary tuberculosis (TB) and mucosal tuberculosis, is a weak antimicrobial drug, the effect is only 2% of streptomycin, often combined with streptomycin and isoniazid , in order to enhance the curative effect.
2-Hydroxybenzoic acid can be acetylated to the aspirin.
Uses
2-Hydroxybenzoic acid is an FDA approved skin care ingredient used for the topical treatment of acne, and it's the only beta hydroxy acid (BHA) used in skin care products.
Perfect for oily skin, 2-Hydroxybenzoic acid is best known for its ability to deep clean excess oil out of pores and reduce oil production moving forward.
Because 2-Hydroxybenzoic acid keeps pores clean and unclogged, it prevents future whiteheads and blackheads from developing.
2-Hydroxybenzoic acid also exfoliates dead skin, and its anti-inflammatory properties make it a prime ingredient for those with psoriasis.
2-Hydroxybenzoic acid naturally occurs in willow bark, sweet birch bark, and wintergreen leaves, but synthetic versions are also used in skin care products.
2-Hydroxybenzoic acid is widely used, eczema, psoriasis, salicylic acid can be used in acne, dandruff.
The concentration of 3%~6% can be used to horny, higher than 6% of salicylic acid can damage to tissue.
Below 40% of concentration is suitable for the treatment of thick cocoon, corns and warts.
2-Hydroxybenzoic acid can also be added in the treatment of acne and dandruff.
Nowadays many famous cosmetic ingredients: in 1993, Clinique CLINIQUE first launched 1% 2-Hydroxybenzoic acid in soft water cream, immediately became one of Clinique's most successful products; In 1998, SK-II crystal induced skin cream added 1.5%BHA ingredients to the original, and 2-Hydroxybenzoic acid has effect of treatment pores and cutin like the egg peeling analogy that caused the market boom; open access Olay popular products activating cream also contains 1.5% BHA components.
However, due to the high concentration of 2-Hydroxybenzoic acid, it has a certain degree of damage, cosmetics containing salicylic acid concentration has generally been limited between 0.2%~1.5%, containing 2-Hydroxybenzoic acid cosmetics shall be added to the note of warning signs to determine the safety of long-term use and children under 3 years of age also shall not be used.
Although toxic in large quantities, 2-Hydroxybenzoic acid is used as a food preservative and as bactericidal and an antiseptic.
For some people with salicylate sensitivity even these small doses can be harmful.
2-Hydroxybenzoic acid is a useful phosphor in the vacuum ultraviolet with nearly flat quantum efficiency for wavelengths between 10 to 100 nm.
2-Hydroxybenzoic acid fluoresces in the blue at 420 nm.
2-Hydroxybenzoic acid is easily prepared on a clean surface by spraying a saturated solution of the salt in methanol followed by evaporation.
salicylic acid is a beta-hydroxy acid with keratolytic and antiinflammatory activity.
2-Hydroxybenzoic acid helps dissolve the top layer of stratum corneum cells, improving the look and feel of the skin.
2-Hydroxybenzoic acid is an effective ingredient in acne products and as such is widely used in acne soaps and lotions.
Because 2-Hydroxybenzoic acid is lipid soluble, it can more easily reduce sebaceous follicle blockage by penetrating the pores and exfoliating the cellular buildup.
2-Hydroxybenzoic acid is antimicrobial, anti-septic, enhances the activity of preservatives, and can be used to adjust the pH of products.
For the treatment of aging skin, it appears to help improve skin wrinkles, roughness, and tone.
In addition, 2-Hydroxybenzoic acid is a useful ingredient for products formulated to treat psoriasis, callouses, corns, and warts-cases where there is a buildup of dead skin cells.
When applied topically, 2-Hydroxybenzoic acid is reported to penetrate 3 to 4 mm into the epidermis.
A small amount of 2-Hydroxybenzoic acid can convert to copper salicylate, a powerful anti-inflammatory used at high concentrations, 2-Hydroxybenzoic acid may cause skin redness and rashes.
This is a naturally occurring organic acid, related to aspirin.
2-Hydroxybenzoic acid is found in some plants, particularly the leaves of wintergreen, willow bark, and the bark of sweet birch.
2-Hydroxybenzoic acid is also synthetically manufactured.
2-Hydroxybenzoic acid is known for its ability to ease aches and pains and reduce fevers.
These medicinal properties, particularly fever relief, have been known since ancient times, and 2-Hydroxybenzoic acid is used as an antiinflammatory drug.
In modern medicine, 2-Hydroxybenzoic acid and its derivatives are used as constituents of some rubefacient products.
For example, 2-Hydroxybenzoic acid is used as a liniment to soothe joint and muscle pain, and choline salicylate is used topically to relieve the pain of mouth ulcers.
As with other beta hydroxy acids, 2-Hydroxybenzoic acid is a key ingredient in many skin-care products for the treatment of seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris, and warts.
2-Hydroxybenzoic acid as a medication is commonly used to remove the outermost layer of the skin.
As such, 2-Hydroxybenzoic acid is used to treat warts, psoriasis, acne vulgaris, ringworm, dandruff, and ichthyosis.
Similar to other hydroxy acids, 2-Hydroxybenzoic acid is an ingredient in many skincare products for the treatment of seborrhoeic dermatitis, acne, psoriasis, calluses, corns, keratosis pilaris, acanthosis nigricans, ichthyosis, and warts.
In the European Union, 2-Hydroxybenzoic acid is regulated as a cosmetic ingredient under Annex III (entry 98) of the Cosmetics Regulation (EC) No 1223/2009.
For uses other than as a preservative 2-Hydroxybenzoic acid is permitted at concentrations up to 3.0% in rinse-off hair products and 2.0% in other products, with a lower limit of 0.5% in certain leave-on products such as body lotion and eye and lip cosmetics; 2-Hydroxybenzoic acid is separately permitted as a preservative at up to 0.5%.
Reflecting its classification as toxic to reproduction (CMR category 2), 2-Hydroxybenzoic acid may not be used in products intended for children under three years of age (other than shampoos), in oral products, or in applications that could be inhaled.
Uses in manufacturing
2-Hydroxybenzoic acid is used as a food preservative, a bactericide, and an antiseptic.
2-Hydroxybenzoic acid is used in the production of other pharmaceuticals, including 4-aminosalicylic acid, sandulpiride, and landetimide (via salethamide).
2-Hydroxybenzoic acid is also used in picric acid production.
2-Hydroxybenzoic acid has long been a key starting material for making acetylsalicylic acid (ASA or aspirin).
2-Hydroxybenzoic acid is prepared by the acetylation of salicylic acid with the acetyl group from acetic anhydride or acetyl chloride.
2-Hydroxybenzoic acid 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 2-Hydroxybenzoic acid, "displays anti-inflammatory action (due to salicylic acid) and also acts as an antacid and mild antibiotic".
2-Hydroxybenzoic acid is an active ingredient in stomach-relief aids such as Pepto-Bismol and some formulations of Kaopectate.
Other derivatives include 2-Hydroxybenzoic acid, used as a liniment to soothe joint and muscle pain, and choline salicylate, which is used topically to relieve the pain of mouth ulcers. 2-Hydroxybenzoic acid is used to induce remission in ulcerative colitis, and has been used as an antitubercular agent often administered in association with isoniazid.
2-Hydroxybenzoic acid is a useful phosphor in the vacuum ultraviolet spectral range, with nearly flat quantum efficiency for wavelengths between 10 and 100 nm.
2-Hydroxybenzoic acid fluoresces in the blue at 420 nm.
2-Hydroxybenzoic acid is easily prepared on a clean surface by spraying a saturated solution of the salt in methanol followed by evaporation.
Clinical Use
The clinical application of aspirin varies with the therapeutic dose.
Low-dose aspirin (75–300mg/day) has antiplatelet aggregation effect and can be used to prevent and treat the coronary and cerebrovascular thrombosis and other postoperative thrombosis.
The middle dose of aspirin (0.5–3 g/day) has antipyretic analgesic effects, so 2-Hydroxybenzoic acid is commonly used in the treatment of fever, headache, toothache, neuralgia, muscle pain and menstrual pain.
High doses of aspirin (more than 4g/day) have anti-inflammatory and antirheumatic effects for the treatment of acute rheumatic fever and rheumatoid arthritis.
In addition, aspirin is used for the treatment of skin and mucous membrane lymphadenopathy (Kawasaki disease) in paediatric.
Benefits for Skin
2-Hydroxybenzoic acid is a beta hydroxy acid that also sloughs dead cell buildup within the follicle, acts as a mild antibacterial, and has soothing properties.
2-Hydroxybenzoic acid is regarded to be less irritating than benzoyl peroxide and has less allergy potential, but it is also less aggressive in treating acne.
2-Hydroxybenzoic acid is often used for treating milder forms of acne.
The concentration in OTC drugs is limited to 2 percent.
2-Hydroxybenzoic acid is also used as a performance ingredient exfoliant in smaller concentrations, without making a drug claim.
Methods of production
1. The phenol and sodium hydroxide react to produce phenol sodium, distillation and dehydration, CO2 carboxylation reaction to obtain sodium salicylate, then using sulfuric acid and produce crude product.
The crude product through the sublimation refined to the finished product.
Raw materials consumption quota: phenol (98%) 704kg/t, alkali burn (95%) 417kg/t, sulfate (95%) 500kg/t, carbon dioxide (99%) 467kg/t.
2.The preparation method of the method is that the sodium salt of phenol and carbon dioxide can be obtained by acidification.
phenol and liquid caustic soda are produced into solution of the sodium salt of phenol, vacuum drying, and then to 100℃, slowly put to the dry carbon dioxide, when the pressure reaches 0.7~0.8MPa, stop passing carbon dioxide, warming up to 140 to 180℃.
After the reaction with water, sodium salicylate dissolved and decolorization, filtering, coupled with the sulfuric acid, namely precipitation salicylic acid, after filtering, washing and drying to obtain the product.
Production Methods
2-Hydroxybenzoic acid may be obtained (1) from oil of wintergreen, which contains methyl salicylate, or (2) by heating dry sodium phenate C6H5ONa plus carbon dioxide under pressure at 130 °C (266 °F) and recovering from the resulting sodium salicylate by adding dilute sulfuric acid.
Production Methods
2-Hydroxybenzoic acid is biosynthesized from the amino acid phenylalanine.
In Arabidopsis thaliana 2-Hydroxybenzoic acid can also be synthesized via a phenylalanine - independent pathway.
2-Hydroxybenzoic acid is commercially prepared by treating sodium phenolate ( the sodium salt of phenol ) with carbon dioxide at high pressure (100 atm ) and high temperature (390K) -a method known as the Kolbe-Schmitt reaction.
Acidification of the product with sulfuric acid gives salicylic acid :
2-Hydroxybenzoic acid can also be prepared by the hydrolysis of aspirin (acetylsalicylic acid) or methyl salicylate (oil of winter green) with a strong acid or base.
