Propyl gallate

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
ChEMBL	ChEMBL7983
ChemSpider	4778
EC Number	204-498-2
Jmol interactive 3D	Image
MeSH	Propyl+Gallate
PubChem	4947
UNII	8D4SNN7V92
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 Key: ZTHYODDOHIVTJV-UHFFFAOYSA-N 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).
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Infobox references

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.

Uses

Propyl gallate is used to protect oils and fats in products from oxidation; it is used in foods, cosmetics, hair products, adhesives, and lubricants.

It is used as a triplet state quencher and an antioxidant in fluorescence microscopy.^[2]

Biological effects

A 1993 study in rodents found a correlation between ingestion of propyl gallate and carcinogenesis.^[3]

A 2009 study found that propyl gallate acts as an estrogen antagonist.^[4]

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.
2. Jerker Widengren, Andriy Chmyrov, Christian Eggeling, Per-Åke Löfdahl, and Claus A. M. Seidel (2007). "Strategies to Improve Photostabilities in Ultrasensitive Fluorescence Spectroscopy". The Journal of Physical Chemistry A 111 (3): 429–440. doi:10.1021/jp0646325. PMID 17228891.
3. 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.
4. Alessio Amadasi, Andrea Mozzarelli, Clara Meda, Adriana Maggi and 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.