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Propyl gallate

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Propyl gallate, or propyl 3,4,5-trihydroxybenzoate, is an ester formed by the condensationofgallic acid and propanol. Since 1948, this antioxidant has been added to foods containing oils and fats to prevent oxidation.^[1] As a food additive, it is used under the E number E310.

Propyl gallate
Names


IUPAC name Propyl 3,4,5-trihydroxybenzoate
Other names Gallic acid, propyl ester n-Propyl gallate E310
Identifiers
CAS Number	121-79-9^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL7983^Y
ChemSpider	4778^Y
ECHA InfoCard	100.004.090
EC Number	204-498-2
E number	E310 (antioxidants, ...)
MeSH	Propyl+Gallate
PubChem CID	4947
UNII	8D4SNN7V92^Y
CompTox Dashboard (EPA)	DTXSID5021201
InChI InChI=1S/C10H12O5/c1-2-3-15-10(14)6-4-7(11)9(13)8(12)5-6/h4-5,11-13H,2-3H2,1H3^Y Key: ZTHYODDOHIVTJV-UHFFFAOYSA-N^Y InChI=1/C10H12O5/c1-2-3-15-10(14)6-4-7(11)9(13)8(12)5-6/h4-5,11-13H,2-3H2,1H3 Key: ZTHYODDOHIVTJV-UHFFFAOYAT
SMILES O=C(OCCC)c1cc(O)c(O)c(O)c1
Properties
Chemical formula	C₁₀H₁₂O₅
Molar mass	212.20 g/mol
Appearance	White crystalline powder
Melting point	150 °C (302 °F; 423 K)
Boiling point	Decomposes
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references

Description

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Propyl gallate is an antioxidant. It protects against oxidation by hydrogen peroxide and oxygen free radicals. It appears as a white to creamy-white crystalline odorless solid.^[2]^[3]

Production

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Propyl gallate does not occur naturally, and is prepared either from reactions with gallic acid and 1-propanol, or by enzyme catalysisoftannic acid.^[4] Syntheses with gallic acid have been the most prominent methods of production, and include Steglich esterification with N,N'-diisopropylcarbodiimide and 4-dimethylaminopyridine, anhydrous addition of thionyl chloride, and Fischer esterification with various catalysts.^[5]

Uses

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Propyl gallate is used to protect oils and fats in products from oxidation; it is used in foods, cosmetics, hair products, adhesives, biodiesel, and lubricants.^[6] It is often used interchangeably with octyl gallate and dodecyl gallate in these applications.^[3]

It is used as a triplet state quencher and an antioxidant in fluorescence microscopy.^[7]

Biological effects

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A 1993 study in fat rodents found little or no effect on carcinogenesis by propyl gallate.^[8]

A 2009 study found that propyl gallate acts as an estrogen antagonist.^[9]

References

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^ "Final Report on the Amended Safety Assessment of Propyl Gallate". International Journal of Toxicology. 26 (suppl. 3): 89–118. 2007. doi:10.1080/10915810701663176. ISSN 1091-5818. PMID 18080874. S2CID 39562131.

^ Gálico, D. A.; Nova, C. V.; Guerra, R. B.; Bannach, G. (2015-09-01). "Thermal and spectroscopic studies of the antioxidant food additive propyl gallate". Food Chemistry. 182: 89–94. doi:10.1016/j.foodchem.2015.02.129. ISSN 0308-8146.

^ ^a ^b EFSA Panel on Food additives and Nutrient Sources added to Food (ANS) (2014). "Scientific Opinion on the re-evaluation of propyl gallate (E 310) as a food additive". EFSA Journal. 12 (4). doi:10.2903/j.efsa.2014.3642.

^ Nie, Guangjun; Liu, Hui; Chen, Zhen; Wang, Peng; Zhao, Genhai; Zheng, Zhiming (2012). "Synthesis of propyl gallate from tannic acid catalyzed by tannase from Aspergillus oryzae: Process optimization of transesterification in anhydrous media". Journal of Molecular Catalysis. 82: 102–108. doi:10.1016/j.molcatb.2012.06.003. ISSN 1381-1177.

^ Nguyen, Van Hai; Le, Minh Ngoc; Nguyen, Hoa Binh; Ha, Kieu Oanh; Pham, Thai Ha Van; Nguyen, Thi Hong; Dao, Nguyet Suong Huyen; Nguyen, Van Giang; Nguyen, Dinh Luyen; Trinh, Nguyen Trieu (2021-04-12). "Propyl Gallate". Molbank. 2021 (2): M1201. doi:10.3390/M1201. ISSN 1422-8599.

^ Hosseinzadeh-Bandbafha, Homa; Kumar, Dipesh; Singh, Bhaskar; Shahbeig, Hossein; Lam, Su Shiung; Aghbashlo, Mortaza; Tabatabaei, Meisam (2022-07-01). "Biodiesel antioxidants and their impact on the behavior of diesel engines: A comprehensive review". Fuel Processing Technology. 232: 107264. doi:10.1016/j.fuproc.2022.107264. ISSN 0378-3820.

^ Jerker Widengren; Andriy Chmyrov; Christian Eggeling; Per-Åke Löfdahl & Claus A. M. Seidel (2007). "Strategies to Improve Photostabilities in Ultrasensitive Fluorescence Spectroscopy". The Journal of Physical Chemistry A. 111 (3): 429–440. Bibcode:2007JPCA..111..429W. doi:10.1021/jp0646325. PMID 17228891.

^ Hirose, Masao, et al..『Modification of carcinogenesis by α-tocopherol, t-butylhydro-quinone, propyl gallate and butylated hydroxytoluene in a rat multi-organ carcinogenesis model.』Carcinogenesis 14.11 (1993): 2359-2364.

^ Alessio Amadasi; Andrea Mozzarelli; Clara Meda; Adriana Maggi; Pietro Cozzini (2009). "Identification of Xenoestrogens in Food Additives by an Integrated in Silico and in Vitro Approach". Chem. Res. Toxicol. 22 (1): 52–63. doi:10.1021/tx800048m. PMC 2758355. PMID 19063592.

Retrieved from "https://en.wikipedia.org/w/index.php?title=Propyl_gallate&oldid=1228037844" Last edited on 9 June 2024, at 04:07

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