Propylparaben

Last updated
Propylparaben
Propylparaben.svg
Propylparaben ball-and-stick.png
Names
Preferred IUPAC name
Propyl 4-hydroxybenzoate
Other names
  • Propyl paraben
  • Propyl p-hydroxybenzoate
  • Propyl parahydroxybenzoate
  • Nipasol
  • E216
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.098 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 202-307-7
E number E216 (preservatives)
KEGG
PubChem CID
UNII
  • InChI=1S/C10H12O3/c1-2-7-13-10(12)8-3-5-9(11)6-4-8/h3-6,11H,2,7H2,1H3 Yes check.svgY
    Key: QELSKZZBTMNZEB-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H12O3/c1-2-7-13-10(12)8-3-5-9(11)6-4-8/h3-6,11H,2,7H2,1H3
    Key: QELSKZZBTMNZEB-UHFFFAOYAD
  • O=C(OCCC)c1ccc(O)cc1
Properties
C10H12O3
Molar mass 180.203 g·mol−1
Density 1.0630 g/cm3
Melting point 96 to 99 °C (205 to 210 °F; 369 to 372 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Related compounds
Related compounds
 Paraben
Butylparaben
Ethylparaben
Methylparaben
Heptylparaben
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Propylparaben (also spelled propyl paraben) is the n-propyl ester of p-hydroxybenzoic acid. It occurs as a natural substance found in many plants and some insects. Additionally, it can be manufactured synthetically for use in cosmetics, pharmaceuticals, and foods. [1] It is a member of the class of parabens and can be used as a preservative in many water-based cosmetics, such as creams, lotions, shampoos, and bath products. [2] As a food additive, it has an E number, which is E216.

Contents

Sodium propyl p-hydroxybenzoate, the sodium salt of propylparaben, a compound with formula Na(C3H7(C6H4COO)O), is used similarly as a food additive and as an anti-fungal preservation agent. Its E number is E217.

In 2010, the European Union Scientific Committee on Consumer Safety stated that the use of butylparaben and propylparaben as preservatives in finished cosmetic products as safe to the consumer, as long as the sum of their concentrations does not exceed 0.19%. [3]

Applications

Food

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, and dairy products. [4] It is even found naturally in a plant called Stocksia brahuica. [5] It is often used as a food and cosmetic preservative as it has no odor or taste, and does not change the texture. [4] 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. [4] [6]

Recently, a study of combining plasma-activated water (PAW) with propylparaben 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 because of interfering substances like polysaccharides, proteins, and lipids. With propylparaben and PAW, bacteria 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.

Propylparaben is also used as a food additive, and is designated with the E number E216. Propylparaben is commonly used as a preservative in packaged baked goods, particularly pastries and tortillas. [7] Propylparaben is also a Standardized Chemical Allergen and is used in allergenic testing. [8] [9]

Cosmetic

Propylparaben is one of the most commonly used paraben in cosmetic formulation. [4] It can be found in moisturizers, shampoos, conditioners, makeups, shaving products, and many more. [10] In cosmetic products, propylparaben is typically combined with other parabens (such as methylparaben) or other preservatives to protect against a broader range of microorganisms. [4] 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 propylparaben is 25%. [10] However, cosmetics do not require testing by the FDA prior to sale. [10] While there is no conclusive evidence of harm to human health from propylparaben, more cosmetic companies are creating paraben-free lines, specifically in shampoos. Since parabens can easily absorb through 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. [11]

Pharmaceutical

Used since the mid-1920s as a preservative, parabens are present in eyewashes, pills, cough syrups, injectable solutions, contraceptives, and even weight-gain drinks. [4] Unlike cosmetics where propylparaben is mostly used in the surface, propylparaben is ingested and absorbed. According to a law from the EEC (European Economic Community), the maximum level of parabens in pharmaceutical products is 1% (w/w), [12] much stricter and defined than cosmetics. Propylparaben also cannot be used alone in ophthalmic products, such as eyewash because it may cause irritation at the effective concentration level to have antimicrobial activities. [4]

A MES (Maximal Electroshock) test also shows anticonvulsant activity in propylparaben. Since propylparaben has minimum to no toxicity and well absorbed in the GI tract, it can potentially be develop to new anticonvulsant medicine to control seizures. [6]

Chemical properties

Propylparaben is a stable and non-volatile compound with antimicrobial properties and has been used as preservatives in food for over 50 years. [4] It is typically used in a variety of water-based cosmetics and personal-care products. [13] it is a white crystalline solid with a molecular weight of 202.18 amu. [14] Humans most often absorb the chemical through their skin or ingestion as it is in many cosmetic and food products as an antifungal preservative. [15] [14] It is metabolized in two major pathways leading to the production of either conjugated metabolites or hydrolysates (PHBA, PHHA). [15] These products are excreted from the body in urine. [15] Propylparaben is an effective antimicrobial, especially against green and blue molds on citrus fruits. [14] Its high solubility in water allows it to be applied to the fruits easily. [14]

Synthesis

One of the simplest ways to produce propylparaben is through the esterification of 4-hydroxy benzoic acid with propanol using an acidic catalyst. [16] 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. [17] 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, propylparaben. [17]

Synthesis of Propyl Paraben by Esterification. Synthesis of Propyl Paraben.jpg
Synthesis of Propyl Paraben by Esterification.

Safety

Propylparaben, among other parabens, has been raising concerns on its possible interaction and disruption of estrogen in the endocrine system [18] Exposure to high levels of propylparaben has been correlated to lower sperm and testosterone production in males in animal studies, [1] [18] with one other study showing that it can even act as an effective spermicide. [19] Animal studies of propylparaben in the body show that propylparaben 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. [18] With cracked or damaged skins, the use of propylparaben in cosmetics or skincare can result in skin sensitization; however, for normal skin, it is considered safe. [5]

As of May 2023, New York began considering banning the use of propylparaben because studies in humans and animals indicate that it acts as an endocrine disruptor and affects reproductive health. [1] [7]

In October 2023, the Governor of California signed a bill into law outlawing the use of propylparaben in foods by 2027. [20] [21] The new law bans the manufacture, sale, and distribution of propylparaben and three other additives (brominated vegetable oil, potassium bromate, and Red 3). This is the first law in the U.S. to ban it and will possibly have nationwide effects. [22]

Related Research Articles

A preservative is a substance or a chemical that is added to products such as food products, beverages, pharmaceutical drugs, paints, biological samples, cosmetics, wood, and many other products to prevent decomposition by microbial growth or by undesirable chemical changes. In general, preservation is implemented in two modes, chemical and physical. Chemical preservation entails adding chemical compounds to the product. Physical preservation entails processes such as refrigeration or drying. Preservative food additives reduce the risk of foodborne infections, decrease microbial spoilage, and preserve fresh attributes and nutritional quality. Some physical techniques for food preservation include dehydration, UV-C radiation, freeze-drying, and refrigeration. Chemical preservation and physical preservation techniques are sometimes combined.

<span class="mw-page-title-main">Butylated hydroxyanisole</span> Chemical compound

Butylated hydroxyanisole (BHA) is a synthetic, waxy, solid petrochemical. Its antioxidant properties have caused it to be widely used as a preservative in food, food packaging, animal feed, cosmetics, pharmaceuticals, rubber, and petroleum products. BHA has been used in food since around 1947.

<span class="mw-page-title-main">Phthalates</span> Any ester derived from phthalic acid

Phthalates ( ), or phthalate esters, are esters of phthalic acid. They are mainly used as plasticizers, i.e., substances added to plastics to increase their flexibility, transparency, durability, and longevity. They are used primarily to soften polyvinyl chloride (PVC). While phthalates are commonly used as plasticizers, not all plasticizers are phthalates. The two terms are specific, unique, and not used interchangeably.

<span class="mw-page-title-main">Benzalkonium chloride</span> Surfactant and antiseptic agent

Benzalkonium chloride, also known as alkyldimethylbenzylammonium chloride (ADBAC) and by the trade name Zephiran, is a type of cationic surfactant. It is an organic salt classified as a quaternary ammonium compound. ADBACs have three main categories of use: as a biocide, a cationic surfactant, and a phase transfer agent. ADBACs are a mixture of alkylbenzyldimethylammonium chlorides, in which the alkyl group has various even-numbered alkyl chain lengths.

Brominated vegetable oil (BVO) is a complex mixture of plant-derived triglycerides that have been modified by atoms of the element bromine bonded to the fat molecules. Brominated vegetable oil has been used to help emulsify citrus-flavored beverages, especially soft drinks, preventing them from separating during distribution. Brominated vegetable oil has been used by the soft drink industry since 1931, generally at a level of about 8 ppm. Several countries have banned use of BVO in food and drink products because of the potential for adverse health effects in humans.

<span class="mw-page-title-main">Paraben</span> Class of chemical compounds; esters of parahydroxybenzoic acid

Parabens are chemicals that are commonly used as preservatives in cosmetic and pharmaceutical products. Chemically, they are a series of parahydroxybenzoates or esters of parahydroxybenzoic acid. Research is being conducted to evaluate the potential health implications of paraben usage.

<span class="mw-page-title-main">Erythrosine</span> Iodo-derivative of fluorone used as a pink dye

Erythrosine, also known as Red No. 3, is an organoiodine compound, specifically a derivative of fluorone. It is a pink dye which is primarily used for food coloring. It is the disodium salt of 2,4,5,7-tetraiodofluorescein. Its maximum absorbance is at 530 nm in an aqueous solution, and it is subject to photodegradation.

<span class="mw-page-title-main">Potassium bromate</span> Chemical compound

Potassium bromate is a bromate of potassium and takes the form of white crystals or powder. It is a strong oxidizing agent.

<span class="mw-page-title-main">Methylparaben</span> Chemical compound

Methylparaben (methyl paraben) one of the parabens, is a preservative with the chemical formula CH3(C6H4(OH)COO). It is the methyl ester of p-hydroxybenzoic acid.

<span class="mw-page-title-main">Butylparaben</span> Chemical compound

Butylparaben, or butyl p-hydroxybenzoate, is an organic compound with the formula C
4H
9O
2CC
6H
4OH. It is a white solid that is soluble in organic solvents. It has proven to be a highly successful antimicrobial preservative in cosmetics. It is also used in medication suspensions, and as a flavoring additive in food.

<span class="mw-page-title-main">Propyl gallate</span> Chemical compound

Propyl gallate, or propyl 3,4,5-trihydroxybenzoate, is an ester formed by the condensation of gallic acid and propanol. Since 1948, this antioxidant has been added to foods containing oils and fats to prevent oxidation. As a food additive, it is used under the E number E310.

<i>tert</i>-Butylhydroquinone Chemical compound

tert-Butylhydroquinone is a synthetic aromatic organic compound which is a type of phenol. It is a derivative of hydroquinone, substituted with a tert-butyl group.

<span class="mw-page-title-main">Benzethonium chloride</span> Chemical compound

Benzethonium chloride, also known as hyamine is a synthetic quaternary ammonium salt. This compound is an odorless white solid, soluble in water. It has surfactant, antiseptic, and anti-infective properties and it is used as a topical antimicrobial agent in first aid antiseptics. It is also found in cosmetics and toiletries such as soap, mouthwashes, anti-itch ointments, and antibacterial moist towelettes. Benzethonium chloride is also used in the food industry as a hard surface disinfectant.

<span class="mw-page-title-main">Formaldehyde releaser</span> Chemical compound used as a preservative

A formaldehyde releaser, formaldehyde donor or formaldehyde-releasing preservative is a chemical compound that slowly releases formaldehyde. Formaldehyde-releasers are added to prevent microbial growth and extend shelf life. The intent of these compounds is that they release formaldehyde at levels that suppress microbial growth but sufficiently low to not threaten humans. The use of these chemicals in cosmetics has elicited controversy.

<span class="mw-page-title-main">Propyl benzoate</span> Chemical compound

Propyl benzoate is an organic chemical compound used as a food additive. It is an ester.

<span class="mw-page-title-main">Sodium bisulfite</span> Chemical compound

Sodium bisulfite (or sodium bisulphite, sodium hydrogen sulfite) is a chemical mixture with the approximate chemical formula NaHSO3. Sodium bisulfite is not a real compound, but a mixture of salts that dissolve in water to give solutions composed of sodium and bisulfite ions. It appears in form of white or yellowish-white crystals with an odor of sulfur dioxide. Regardless of its ill-defined nature, sodium bisulfite is used in many different industries such as a food additive with E number E222 in the food industry, a reducing agent in the cosmetic industry, and a decomposer of residual hypochlorite used in the bleaching industry.

Nipastat is the brand name for a mixture of parabens (parahydroxybenzoates) by Clariant, a chemicals company. Parabens are a type of compound used as a preservative in pharmaceuticals, cosmetics, and food. Nipastat is a white powder at room temperature, but is typically dissolved into a liquid product. Nipastat acts to prevent the growth of bacteria, mold, and yeast. Nipastat is a mixture of five common parabens: methylparaben (50-60%), butylparaben (12-17%), ethylparaben, (13-18%) propylparaben (6-9%), and isobutylparaben (6-9%). When Nipastat is added to a product, the recommended final weight of Nipastat is between 0.05% and 0.3% of the total weight. Nipastat is stable at a range of pHs between 4 and 8.

Antiandrogens in the environment have become a topic of concern. Many industrial chemicals, including phthalates and pesticides, exhibit antiandrogen activity in animal experiments. Certain plant species have also been found to produce antiandrogens. In animal studies, environmental antiandrogens can harm reproductive organ development in fetuses exposed in utero as well as their offspring.

<span class="mw-page-title-main">Ethyl lauroyl arginate</span> Chemical compound

Ethyl lauroyl arginate (LAE) is a food preservative, antimicrobial compound, and drug more commonly known as E243. It is used to treat dermatological disorders and is often provided in the form of its hydrochloride salt. LAE is an amino acid-based surfactant with broad-spectrum antimicrobial activity, high biodegradability and low toxicity. Due to these features, LAE is a preservative used in food and cosmetic formulations.

References

  1. 1 2 3 Oishi (December 2002). "Effects of propyl paraben on the male reproductive system". Food and Chemical Toxicology. 40 (12): 1807–1013. doi:10.1016/s0278-6915(02)00204-1. PMID   12419695.
  2. ↑ PubChem. "Propylparaben". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-12-01.
  3. ↑ Directorate-General for Consumer Safety, European Union (2011). "Scientific Committee on Consumer Safety Opinion on Parabens COLIPA n° P82" (PDF). Retrieved December 15, 2017.
  4. 1 2 3 4 5 6 7 8 Soni, M. G.; Burdock, G. A.; Taylor, S. L.; Greenberg, N. A. (June 2001). "Safety assessment of propyl paraben: a review of the published literature". Food and Chemical Toxicology. 39 (6): 513–532. doi:10.1016/S0278-6915(00)00162-9. ISSN   0278-6915. PMID   11346481.
  5. 1 2 Soni, M.G.; Carabin, I.G.; Burdock, G.A. (July 2005). "Safety assessment of esters of p-hydroxybenzoic acid (parabens)". Food and Chemical Toxicology. 43 (7): 985–1015. doi:10.1016/j.fct.2005.01.020. PMID   15833376.
  6. 1 2 Talevi, Alan; Bellera, Carolina L.; Castro, Eduardo A.; Bruno-Blanch, Luis E. (2007-10-25). "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. 21 (9): 527–538. Bibcode:2007JCAMD..21..527T. doi:10.1007/s10822-007-9136-9. ISSN   0920-654X. PMID   17960329.
  7. 1 2 Dana G. Smith (April 13, 2023). "Two States Have Proposed Bans on Common Food Additives Linked to Health Concerns". New York Times. Retrieved May 23, 2023.
  8. ↑ "DailyMed - Browse Drug Classes". dailymed.nlm.nih.gov. Retrieved 2021-12-01.
  9. ↑ "Propylparaben". go.drugbank.com. Retrieved 2021-12-01.
  10. 1 2 3 Center for Food Safety and Applied Nutrition (2022-03-03). "Parabens in Cosmetics". FDA.
  11. ↑ Jones, Oliver A. H. (2023-03-27). "What is a paraben and why are so many products advertised as 'paraben-free'?". The Conversation. Retrieved 2023-11-10.
  12. ↑ "EUR-Lex - l21191 - EN - EUR-Lex". eur-lex.europa.eu. Retrieved 2023-11-10.
  13. ↑ "propylparaben (CHEBI:32063)". www.ebi.ac.uk. Retrieved 2021-12-01.
  14. 1 2 3 4 Moscoso-Ramírez, Pedro A.; Montesinos-Herrero, Clara; Palou, Lluís (September 2014). "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. 140 (1): 145–157. Bibcode:2014EJPP..140..145M. doi:10.1007/s10658-014-0450-5. ISSN   0929-1873.
  15. 1 2 3 Shin, Mi-Yeon; Shin, Chorong; Choi, Jeong Weon; Lee, Jangwoo; Lee, Seungho; Kim, Sungkyoon (September 2019). "Pharmacokinetic profile of propyl paraben in humans after oral administration". Environment International. 130. 104917. Bibcode:2019EnInt.13004917S. doi: 10.1016/j.envint.2019.104917 . ISSN   0160-4120. PMID   31234001.
  16. ↑ Hazarika, Mridul; Parajuli, Raghab; Phukan, Prodeep (January 2007). "Synthesis of parabens using montmorillonite K10 clay as catalyst: A green protocol" (PDF). Indian Journal of Chemical Technology. 14: 104–106.
  17. 1 2 "21.6: Chemistry of Esters". Chemistry LibreTexts. 2015-08-26. Retrieved 2023-11-26.
  18. 1 2 3 Boberg, Julie; Taxvig, Camilla; Christiansen, Sofie; Hass, Ulla (September 2010). "Possible endocrine disrupting effects of parabens and their metabolites". Reproductive Toxicology. 30 (2): 301–312. Bibcode:2010RepTx..30..301B. doi:10.1016/j.reprotox.2010.03.011. PMID   20381602.
  19. ↑ Bao-Liang, Song; Hai-Ying, Li; Dun-Ren, Peng (March 1989). "In vitro spermicidal activity of parabens against human spermatozoa". Contraception. 39 (3): 331–335. doi:10.1016/0010-7824(89)90065-6. PMID   2714092.
  20. ↑ "AB-418 The California Food Safety Act". ca.gov.
  21. ↑ Chuck, Elizabeth (2023-09-12). "California Legislature passes first bill in U.S. to ban food additives, including red dye No. 3". www.nbcnews.com. Retrieved 2023-09-14.
  22. ↑ Cimons, Marlene (Oct 11, 2023). "California isn't banning Skittles, but four additives will be removed" . Washington Post. The article notes that Red dye No. 3, bromated vegetable oil, potassium bromate and propyl paraben all have been linked to risk of cancer and hyperactivity in children.
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