Propyl gallate

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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

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

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. S2CID 39562131
    .
  2. ISSN 0308-8146
    .
  3. ^
    doi:10.2903/j.efsa.2014.3642
    .
  4. ISSN 1381-1177
    .
  5. ISSN 1422-8599
    .
  6. ISSN 0378-3820
    .
  7. 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. PMID 19063592
    .
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