Propyl gallate
Structural formula of propyl gallate
Space-filling model of the propyl gallate molecule
Names
IUPAC name
Propyl 3,4,5-trihydroxybenzoate
Other names
Gallic acid, propyl ester
n-Propyl gallate
E310
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.090 Edit this at Wikidata
EC Number
  • 204-498-2
E number E310 (antioxidants, ...)
MeSH Propyl+Gallate
UNII
  • 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 checkY
    Key: ZTHYODDOHIVTJV-UHFFFAOYSA-N checkY
  • 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
  • O=C(OCCC)c1cc(O)c(O)c(O)c1
Properties
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).
checkY verify (what is checkY☒N ?)

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.[1] As a food additive, it is used under the E number E310.

Description

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

Propyl gallate does not occur naturally, and is prepared either from reactions with gallic acid and 1-propanol, or by enzyme catalysis of tannic 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

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

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

  1. ^ "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.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
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