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Synthesis of Salicylic Acid

Synthesis of Salicylic Acid 20
The Synthesis, Properties, Application of Salicylic Acid in the Treatment of Acne Jenny Pham CHEM 4201 – Spring 2014 Introduction ☤Salicylic Acid – name derived from Salix (Latin name for the willow tree) ☤Organic Compound – Chemically Synthesized Biosynthesized ☤Functions as a Hormone in Plants – Defense Against Pathogens ☤Vast Array of Benefits Uses • Applications in Food Chemistry, Textiles, Medicine, Cosmetics, Dermatology  Food Chemistry – preservative  Textiles – synthesis of dyes; used for its antibacterial properties  Medicine – relieve fever and pain  Cosmetics – preservative; has exfoliating and cleansing properties  Dermatology – seborrheic dermatitis, viral warts, psoriasis, acne vulgaris, and more Background ☤4000 BC – Assyrians used the extracts of willow leaves to treat painful musculoskeletal joint pain conditions, as well as an antipyretic drug to reduce fever. ☤400 BC – Hippocrates (Greek physician; known as the “father of Western medicine”) used willow bark extract to treat fever and relieve pain associated with childbirth. st ☤1828 – Johann Buchner was the 1 to extract and purify salicin (later determined to be the pharmacological active compound in 1935 by Raffaele Piria) from willow bark. ☤1859 – Kolbe Schmitt discovered the KolbeSchmitt reaction to chemically synthesize salicylic acid from phenol, allowing for it to be produced on a large commercial scale. st ☤1893 – Felix Hoffman was the 1 to synthesize pure and stable acetylsalicylic acid (known as aspirin). Synthesis of Salicylic Acid ☤Synthesis From Natural Sources ☤Industrial Synthesis Synthesis from Natural Sources ☤Salicylaldehyde from Meadowsweet Flowers (Filipendula ulmaria) • Extracted by Pagenstecher (Swiss pharmacist) as early as 1835. • Oxidized by Lowig (German chemist). Industrial Synthesis from Phenol ☤KolbeSchmitt Reaction by Hermann Kolbe Rudolf Schmitt in 1859 Chemical Properties ☤Common Name: Salicylic Acid ☤Molecular Formula: C H O 7 6 3 ☤Molecular Weight: 138.12074 g/mol ☤IUPAC Name: 2hydroxybenzoic acid → αhydroxy acid ☤Appearance: Colorless Crystalline Powder to White NeedleShaped Crystals ☤Odor: Odorless ☤Taste: Acrid Beneficial Properties ☤Antibacterial ☤AntiInflammatory ☤Antifungal ☤Keratolytic ☤Antiseptic ☤Comedolytic ☤Antipyretic ☤Bacteriostatic What is Acne Vulgaris ☤It’s a common chronic disease of the pilosebasceous unit of the skin, affecting more than 80 of adolescents and often persists into adulthood ☤Cause – obstruction of the pilosebasceous canal ☤Characteristics • oily skin (excess sebum production) • noninflammatory lesions (open/closed comedones) • inflammatory lesions (papules, pustules, and nodules) ☤Normally affects the face, upper chest, and back – areas that have the densest amount of sebaceous follicles. Salicylic Acid – Acne Treatment ☤Salicylic acid is applied topically to the skin affected by acne vulgaris. • strong keratolytic and comdelytic agent • increases penetration of other products • has a slight antiinflammatory effect • bacteriostatic and fungistatic at low concentrations – competitive inhibition of pantothenic acid Written Component ☤Designing an experiment that incorporates the synthesis of salicylic acid from a natural source, such as the flowers of the meadowsweet plant, wintergreen plant, or bark from the willow tree, and utilizing the salicylic acid to make a more natural product used to treat acne, rather than using industrially synthesized salicylic acid. References 1. Mahdi, J. (2010). Medicinal potential of willow: A chemical perspective of aspirin discovery. Journal of Saudi Chemical Society, 14(3), 317322. 2. Vlot, A., Dempsey, D., Klessig, D. (2009). Salicylic Acid, a Multifaceted Hormone to Combat Disease. Annual Review of Phytopathology, 47, 177206. 3. Jack, D. B. (1997). One hundred years of aspirin. The Lancet, 350(9075), 437439. 4. Kantouch, A., ElSayed, A., Salama, M., ElKheir, A., Mowafi, S. (2013). Salicylic acid and some of its derivatives as antibacterial agents for viscose fabric. International Journal of Biological Macromolecules, 62, 603607. 5. Young, J. (2008). Salicylic Acid. Journal of Chemical Education, 85(12), 1617. 6. Kornhauser, A., Coelho, S. G., Hearing, V. J. (2010). Applications of hydroxy acids: classification, mechanisms, and photoactivity. Clinical, Cosmetic and Investigational Dermatology : CCID, 3, 135–142. doi:10.2147/CCID.S9042 7. Sladden, M. J., Johnston, G. A. (2004). Common skin infections in children. BMJ : British Medical Journal, 329(7457), 95–99. 8. Salicylic Acid PubChem. (2004, September 16). Retrieved November 15, 2014, from 9. Chemistry Experiments: Salicylic Acid and Salicylates. Retrieved November 18, 2014, from 10. White Willow Bark Organic. Retrieved November 17, 2014, from 11. Filipendula rubra. (2014, November 19). Retrieved November 22, 2014, from 12. Native Plants for NYC Fall Color. Retrieved November 17, 2014, from 13. KolbeSchmitt Reaction. Retrieved November 16, 2014, from 14. Strom, M., Lio, P. (2014). Alternative Medicine in Pediatric Dermatology: What Is the Evidence Current Dermatology Reports, 3(4), 165170. 15. Krautheim, A., Gollnick, H. (2012). Transdermal Penetration of Topical Drugs Used in the Treatment of Acne. Clinical Pharmacokinetics, 42(14), 1287 1304. 16. Comedogenesis: Inflammation, Androgens, Sebum Lipid and Cytokines. Retrieved November 22, 2014, from vulgariscomedogenesistheroleofinflammationandrogenssebumlipidandcytokines/ 17. Bowe, W., Glick, J., Shalita, A. (2012). Solodyn and Updates on Topical and Oral Therapies for Acne. Current Dermatology Reports, 1(3), 97107. 18. Natural Acne Solutions. Retrieved November 22, 2014, from,default,sc.html
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