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Synthesis of Salicylic Acid
Synthesis of Salicylic Acid 20
Properties, & Application
of Salicylic Acid in the
Treatment of Acne
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
☤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.
☤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 Kolbe-Schmitt reaction to chemically synthesize
salicylic acid from phenol, allowing for it to be produced on a large commercial scale.
☤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
☤Salicylaldehyde from Meadowsweet Flowers (Filipendula ulmaria)
• Extracted by Pagenstecher (Swiss pharmacist) as early as 1835.
• Oxidized by Lowig (German chemist). Industrial Synthesis from
☤Kolbe-Schmitt 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: 2-hydroxybenzoic acid → α-hydroxy acid
☤Appearance: Colorless Crystalline Powder to White Needle-Shaped Crystals
☤Taste: Acrid Beneficial Properties
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
• oily skin (excess sebum production)
• non-inflammatory lesions (open/closed
• inflammatory lesions (papules, pustules, and
☤Normally affects the face, upper chest, and back –
areas that have the densest amount of sebaceous
Salicylic Acid – Acne
☤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 anti-inflammatory effect
• bacteriostatic and fungistatic at low concentrations – competitive inhibition of pantothenic acid
☤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), 317-322.
2. Vlot, A., Dempsey, D., & Klessig, D. (2009). Salicylic Acid, a Multifaceted Hormone to Combat Disease. Annual Review of Phytopathology, 47, 177-206.
3. Jack, D. B. (1997). One hundred years of aspirin. The Lancet, 350(9075), 437-439.
4. Kantouch, A., El-Sayed, A., Salama, M., El-Kheir, A., & Mowafi, S. (2013). Salicylic acid and some of its derivatives as antibacterial agents for viscose
fabric. International Journal of Biological Macromolecules, 62, 603-607.
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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
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8. Salicylic Acid - PubChem. (2004, September 16). Retrieved November 15, 2014, from http://pubchem.ncbi.nlm.nih.gov/compound/338
9. Chemistry Experiments: Salicylic Acid and Salicylates. Retrieved November 18, 2014, from http://www.crscientific.com/article-aspirin.html
10. White Willow Bark Organic. Retrieved November 17, 2014, from http://eternityinabox.com/shop/white-willow-bark-organic/
11. Filipendula rubra. (2014, November 19). Retrieved November 22, 2014, from http://en.wikipedia.org/wiki/Filipendula_rubra5
12. Native Plants for NYC Fall Color. Retrieved November 17, 2014, from http://newecolandscapes.com/5-native-plants-for-fall-color/
13. Kolbe-Schmitt Reaction. Retrieved November 16, 2014, from http://www.chem.ucla.edu/harding/IGOC/K/kolbe_schmitt_reaction.html
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15. Krautheim, A., & Gollnick, H. (2012). Transdermal Penetration of Topical Drugs Used in the Treatment of Acne. Clinical Pharmacokinetics, 42(14), 1287-
16. Comedogenesis: Inflammation, Androgens, Sebum Lipid and Cytokines. Retrieved November 22, 2014, from http://health.tipsdiscover.com/acne-
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