User:Dev1 0302/Propylparaben

Bibliography

Properties

Antifungal activity of sodium propylparaben alone or in combination with low doses of imazalil against Penicillium decay on citrus fruit

https://redivia.gva.es/bitstream/handle/20.500.11939/5700/2014_Moscoso-Ram%C3%ADrez_Antifungal_Post-Print.pdf?sequence=1

- Sodium propyl paraben is an affective treatment against disease in post harvest fruits and vegetables.

-effective in controlling citrus green and blue molds

Moscoso-Ramírez, P. A.; Montesinos-Herrero, C.; Palou, L. Antifungal Activity of Sodium Propylparaben Alone or in Combination with Low Doses of Imazalil against Penicillium Decay on Citrus Fruit. European Journal of Plant Pathology 2014, 140, 145–157.

Antifungal effect of different methyl and propyl paraben mixtures on the treatment of paper biodeterioration

https://doi.org/10.1016/j.ibiod.2008.07.011

- Propyl Paraben effectively inhibits fungal growth

Citation:

Neves, E. R.; Schäfer, S.; Phillips, A.; Canejo, J.; Macedo, M. F. Antifungal Effect of Different Methyl and Propyl Paraben Mixtures on the Treatment of Paper Biodeterioration. International Biodeterioration & Biodegradation 2009, 63, 267–272.

Possible Health hazards

Pharmacokinetic profile of propyl paraben in humans after oral administration:

https://doi.org/10.1016/j.envint.2019.104917

- Describes how humans metabolize Propyl paraben

- provides a pharmacokinetic profile of propyl paraben in humans

-Found that: "PP was rapidly absorbed via ingestion within 2 h and quickly eliminated"

Citation:

Shin, M.-Y.; Shin, C.; Choi, J. W.; Lee, J.; Lee, S.; Kim, S. Pharmacokinetic Profile of Propyl Paraben in Humans after Oral Administration. Environment International 2019, 130, 104917. 

Possible endocrine disrupting effects of parabens and their metabolites

https://doi.org/10.1016/j.reprotox.2010.03.011

- parabens (general) disrupts estrogen in endocrine system

Citation:

Boberg, J.; Taxvig, C.; Christiansen, S.; Hass, U. Possible Endocrine Disrupting Effects of Parabens and Their Metabolites. Reproductive Toxicology 2010, 30, 301–312.

In vitro spermicidal activity of parabens against human spermatozoa

https://doi.org/10.1016/0010-7824(89)90065-6

- propyl paraben, among other parabens, is an effective spermicide in vitro.

Citation:

Bao-Liang, S.; Hai-Ying, L.; Dun-Ren, P. In Vitro Spermicidal Activity of Parabens against Human Spermatozoa. Contraception 1989, 39, 331–335.

Effects of propyl paraben on the male reproductive system

https://doi.org/10.1016/S0278-6915(02)00204-1

-Reduces the production of sperm in rats at the daily limit dose (10mg/ kg body weight per day) in Europe and Japan

Citation

Oishi, S. Effects of Propyl Paraben on the Male Reproductive System. Food and Chemical Toxicology 2002, 40, 1807–1813.

Application

1.Food

Propylparaben is a stable and non-volatile compound with antimicrobial properties and has been used as preservatives in food for over 50 years. Under FDA regulations, Propylparaben is safe to use with a maximum of 0.1% of the weight of the finished food or 200 - 450 ppm for a variety of foods like coffee extracts, juices, jams, baked goods, dairy products, etc. It’s even found naturally in foods such as in white wine, cloudberry, strawberries, bourbon vanilla, and a plant called Stocksia brahuica.

Recently, a study of combining PAW with Propylparaben show increased antimicrobial efficacy of PAW for fresh produce sanitation. Plasma-Activated Water (PAW) is used for fresh produce sanitation. However when used in food applications, its effectiveness decreased due to interfering substances like polysaccharides, proteins, and lipids. With propylparaben and PAW, bacterias undergo more oxidative stress and cell damage, increasing preservation of produce. For now, The potential health risk and residue level of propylparaben with this new method is still unknown.

2. Cosmetics

Soni, M. G.; Burdock, G. A.; Taylor, S. L.; Greenberg, N. A. Safety Assessment of Propyl Paraben: A Review of the Published Literature. Food and Chemical Toxicology 2001, 39 (6), 513–532. https://doi.org/10.1016/s0278-6915(00)00162-9.

• used as cosmetic preservatives because no odor, taste, and doesn’t change texture

3. Pharmaceutical

Soni, M. G.; Burdock, G. A.; Taylor, S. L.; Greenberg, N. A. Safety Assessment of Propyl Paraben: A Review of the Published Literature. Food and Chemical Toxicology 2001, 39 (6), 513–532. https://doi.org/10.1016/s0278-6915(00)00162-9.

• used in pills, syrups, eyewashes, weight gain drinks

Talevi, A.; Bellera, C. L.; Castro, E. A.; Bruno-Blanch, L. E. A Successful Virtual Screening Application: Prediction of Anticonvulsant Activity in MES Test of Widely Used Pharmaceutical and Food Preservatives Methylparaben and Propylparaben. Journal of Computer-Aided Molecular Design 2007, 21 (9), 527–538. https://doi.org/10.1007/s10822-007-9136-9.

• discovered anticonvulsant activities in MES Test with doses of propylparaben that can be used in new developmental anticonvulsant medicine (to control seizures)‌

Safety Issues

Animal studies of propylparaben in the bodies shows that propylparaben gets metabolized from the GI tract and excreted rapidly through urine with no accumulation in the body. With broken or damaged skins use of propylparaben in cosmetics or skincare results in skin sensitization, but in normal skins it’s considered safe and effective. Some research indicates potential estrogenic activity that disrupts reproductive system, [not finished]

Application

Food

Under FDA regulations, Propyl paraben is safe to use with a maximum of 0.1% of the weight of the finished food or 200 - 450 ppm for a variety of foods like coffee extracts, juices, jams, baked goods, dairy products, etc. It’s even found naturally in foods such as in white wine, cloudberry, strawberries, bourbon vanilla, and a plant called Stocksia brahuica. It is often used as a food and cosmetic preservative as it has no odor or taste, and does not change the texture. The compound has some medicinal application as well as it has been used in pills, syrups, eyewashes, weight gain drinks, and recently has been discovered to have anticonvulsant activities suggesting it may be useful in the development of anticonvulsant medicine.

Recently, a study of combining Plasma-Activated Water (PAW) with Propyl paraben show increased antimicrobial efficacy of PAW for fresh produce sanitation. PAW is used for fresh produce sanitation. However when used in food applications, its effectiveness decreased due to interfering substances like polysaccharides, proteins, and lipids. With propyl paraben and PAW, bacteria's undergo more oxidative stress and cell damage, increasing preservation of produce. For now, The potential health risk and residue level of propyl paraben with this new method is still unknown.

Cosmetic

Propyl paraben is one of the most commonly used paraben in cosmetic formulation. It can be found in moisturizers, shampoos, conditioners, makeups, shaving products, and many more. In cosmetic products, Propyl paraben is typically combined with other parabens (i.e Methyl paraben) or other preservatives to protect against a broader range of microorganisms. The chemical stability in room temperature and wide pH range (4.5-7.5) is advantageous to prolong a product shelf-life. Under FDA regulations, the maximum use of concentration for Propyl paraben is 25%. However, cosmetics don't require testing by the FDA before selling. While there's no conclusive evidence of harm to human health from propyl paraben, more cosmetic companies are creating Paraben-free lines, specifically in shampoos. Since paraben can easily absorb through your skin, daily use is believed to cause toxic accumulation in the body that might be harmful. Some people may also experience allergic reaction to parabens including redness, irritation, itchiness, flaking, and hives.

Pharmaceutical

Used since mid 1920s as a preservative, parabens are present in our eyewashes, pills, cough syrups, injectable solutions, contraceptives, even weight-gain drinks. Unlike cosmetics where propyl paraben is mostly used in the surface, propyl paraben is ingested and absorbed. According to the law made by EEC (European Economic Community) , the maximum level of parabens in pharmaceutical products is 1% (w/w), much stricter and defined than cosmetics. Propyl paraben also can't be used alone in ophthalmic products, such as eyewash because it may cause irritation at the effective concentration level to have antimicrobial activities.

A MES (Maximal Electroshock) test also shows anticonvulsant activity in Propyl paraben. Since Propyl paraben has minimum to no toxicity and well absorbed in the GI tract, it can potentially be develop to new anticonvulsant medicine to control seizures.

Chemical Properties

Propyl paraben is a stable and non-volatile compound with antimicrobial properties and has been used as preservatives in food for over 50 years. it is a white crystalline solid with a molecular weight of 202.18 amu. Humans most often absorb the chemical through their skin or ingestion as it is in many cosmetic and food products as an antifungal preservative. It is metabolized in two major pathways leading to the production of either conjugated metabolites or hydrolysates (PHBA, PHHA). These products are excreted from the body in urine. Propyl Paraben is an effective antimicrobial, especially against green and blue molds on citrus fruits. Its high solubility in water allows it to be applied to the fruits easily.

Synthesis

One of the simplest ways to produce Propyl Paraben is through the esterification of 4-hydroxy benzoic acid with propanol using an acidic catalyst . The first major step includes the protonation of the carbonyl due to the acidic conditions. This protonation results in a positive charge on the carbonyl which will offset the electron density from the ester carbon atom, this allows the propanol to preform a nucleophilic attack on the carbonyl. The proton of the nucleophilic propanol is then transferred by the solvent to the esters hydroxyl group. The hydroxyl can then act as a good leaving group and be expelled from the tetrahedral intermediate as water, allowing the ester carbonyl group to reform. Finally, deprotonation of the reformed carbonyl group will produce the final ester product, Propyl Paraben.

Synthesis of Propyl Paraben by Esterification.

Health Considerations

Propyl paraben, among other parabens, has been raising concerns on its possible interaction and disruption of estrogen in the endocrine system Exposure to high levels of propyl parabens has been correlated to lower sperm and testosterone production in males in animal studies. Studies showcase that propyl paraben can even act as an effective spermicide. Animal studies of propyl paraben in the body showcases that propyl paraben is metabolized from the GI tract and excreted rapidly through urine with no accumulation in the body. Despite parabens interaction with the endocrine system it has not been shown to be significantly correlated with breast cancer. With broken or damaged skins the use of propyl paraben in cosmetics or skincare can result in skin sensitization, however for normal skin it is considered safe.