Salicylic Acid

Base Information

• Chemical Name: Salicylic Acid
• CAS No.: 69-72-7
• Deprecated CAS: 7681-06-3,8052-31-1,1186130-36-8,1186130-36-8,8052-31-1
• Molecular Formula: C7H6O3
• Molecular Weight: 138.123
• Hs Code.: 2918.21
• European Community (EC) Number: 200-712-3,308-377-6,305-634-4
• ICSC Number: 0563
• NSC Number: 180
• UNII: O414PZ4LPZ
• DSSTox Substance ID: DTXSID7026368
• Nikkaji Number: J2.370A
• Wikipedia: Salicylic acid
• Wikidata: Q193572
• NCI Thesaurus Code: C61934
• RXCUI: 9525
• Pharos Ligand ID: FBKFP3SAJZML
• Metabolomics Workbench ID: 37916
• ChEMBL ID: CHEMBL424
• Mol file: 69-72-7.mol

Synonyms:2 Hydroxybenzoic Acid;2-Hydroxybenzoic Acid;Acid, 2-Hydroxybenzoic;Acid, o-Hydroxybenzoic;Acid, ortho-Hydroxybenzoic;Acid, Salicylic;o Hydroxybenzoic Acid;o-Hydroxybenzoic Acid;ortho Hydroxybenzoic Acid;ortho-Hydroxybenzoic Acid;Salicylic Acid

Chemical Property of Salicylic Acid

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 158-161 °C(lit.)
• Refractive Index: 1,565
• Boiling Point: 336.28 °C at 760 mmHg
• PKA: 3.01±0.10(Predicted)
• Flash Point: 144.486 °C
• PSA: 57.53000
• Density: 1.376 g/cm³
• LogP: 1.09040
• Water Solubility.: 1.8 g/L (20℃)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 138.031694049
• Heavy Atom Count: 10
• Complexity: 133

Purity/Quality:

98%,99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn:Harmful
• Statements: R22:; R36/37/38:; R41:
• Safety Statements: S26:; S37/39:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Benzoic Acid Derivatives
• Canonical SMILES: C1=CC=C(C(=C1)C(=O)O)O
• Recent ClinicalTrials: Efficacy of 25% Trichloroacetic Acid Peel Versus 30% Salicylic Acid Peel in Mild to Moderate Acne Vulgaris
• Recent EU Clinical Trials: Effect of the administration of 75 mg of acetylsalicylic acid + 200mg of triglycerides of n-3 series fatty acids (omega 3 + ASA) on the biosynthesis of platelet thromboxane A2 in patients with cardiovascular disease.
• Recent NIPH Clinical Trials: Effect of Guselkumab Treatment on Regulatory T-cell Subsets and Dendritic Cells Subsets in Psoriasis Patients
• Inhalation Risk: Evaporation at 20 °C is negligible; a nuisance-causing concentration of airborne particles can, however, be reached quickly when dispersed.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system and acid-base balance in the body. This may result in delirium and tremors.
• Effects of Long Term Exposure: Repeated or prolonged contact with skin may cause dermatitis.
• Plant Defense Hormone: Salicylic acid (SA) functions as an essential plant defense hormone, promoting immunity against biotrophic and hemibiotrophic pathogens. It plays crucial roles in basal defense, amplification of local immune responses, and the establishment of systemic acquired resistance.
• Role in Stress Reduction: SA application can decrease plant stress caused by pollution and climate change. It initiates pathogenesis-related gene expression and synthesis of defensive compounds, enhancing local resistance and systemic acquired resistance. SA may alleviate pathogen virulence, heavy metal stresses, salt stress, and toxicities of other elements.
• Physiological and Biochemical Effects: Applied SA improves photosynthesis, growth, and various physiological and biochemical characteristics in stressed plants. It acts as an antioxidant, scavenging reactive oxygen species, and activating the antioxidant systems of plants. SA also reduces metal uptake from the growth medium, counteracting the oxidative damage caused by metal toxicity.
• Biosynthesis and Signaling Pathways: Salicylic acid is synthesized from chorismate through two distinct pathways in plants: the isochorismate (IC) and the phenylalanine ammonia-lyase (PAL) pathways. It is perceived by receptors such as NPR1 and its paralogues NPR3 and NPR4, stimulating downstream SA-responsive genes and inducing plant immune responses. Various SA-binding proteins (SABPs) may act as potential SA receptors, contributing to SA signaling.
• Modifications and Regulation: Salicylic acid can undergo modifications such as glycosylation, methylation, and amino acid conjugation, rendering it inactive or fine-tuning its accumulation, function, and mobility. These modifications affect the regulation of SA on plant immunity and growth, providing a mechanism for fine-tuning SA-mediated responses in plants.

Technology Process of Salicylic Acid

There total 723 articles about Salicylic Acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

2-bromobenzoic-acid (88-65-3) + methyl salicylate (119-36-8,8024-54-2) → 2-bromobenzoic acid methyl ester (610-94-6) + salicylic acid (69-72-7,25496-36-0,8052-31-1)

Guidance literature:

2-bromobenzoic-acid; With potassium carbonate; In N,N-dimethyl acetamide; at 110 ℃; for 0.5h;

methyl salicylate; at 110 ℃; for 24h;

DOI:10.1055/s-0033-1340285

Reference yield: 90.0%

ortho-chlorobenzoic acid (118-91-2) + methyl salicylate (119-36-8,8024-54-2) → methyl chlorobenzoate (610-96-8) + salicylic acid (69-72-7,25496-36-0,8052-31-1)

Guidance literature:

ortho-chlorobenzoic acid; With potassium carbonate; In N,N-dimethyl acetamide; at 110 ℃; for 0.5h;

methyl salicylate; at 110 ℃; for 24h;

DOI:10.1055/s-0033-1340285

Reference yield: 84.0%

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + methyl salicylate (119-36-8,8024-54-2) → 2-carbomethoxyaniline (134-20-3) + salicylic acid (69-72-7,25496-36-0,8052-31-1)

Guidance literature:

anthranilic acid; With potassium carbonate; In N,N-dimethyl acetamide; at 110 ℃; for 0.5h;

methyl salicylate; at 110 ℃; for 24h;

DOI:10.1055/s-0033-1340285

upstream raw materials:

tetrachloromethane

ethanol

o-benzoyloxybenzoic acid

n-butyllithium

Downstream raw materials:

2-(2-hydroxyethoxy)benzoic acid

1,4-bis-salicyloyloxy-butane

o-benzoyloxybenzoic acid

2-hydroxy-benzoic acid, 2-carboxyphenyl ester

Refernces

• 1、 Anoop, Anakuthil,Dey, Subhasis,Mandal, Sukanta,Podder, Nirmalya. "Oxygenolysis of a series of copper(ii)-flavonolate adducts varying the electronic factors on supporting ligands as a mimic of quercetin 2,4-dioxygenase-like activity". supporting information. p. 4338 - 4353. Retrieved 2022/04/07.
• 2、 Lin, Chuankai,Liu, Jin-Biao,Wang, Ruixiang,Xie, Huilin. "Synthesis of salicylates from anionically activated aromatic trifluoromethyl group". supporting information. . Retrieved 2021/12/22.