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Propyl gallate
Names
IUPAC name
Propyl 3,4,5-trihydroxybenzoate
Other names
Gallic acid, propyl estern
Identifiers
CAS Number
3D model (JSmol )
ChEMBL
ChemSpider
ECHA InfoCard 100.004.090
EC Number
E number E310 (antioxidants, ...)
MeSH
Propyl+Gallate
PubChem CID
UNII
CompTox Dashboard (EPA )
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
O=C(OCCC)c1cc(O )c(O )c(O )c1
Properties
Chemical formula
C 10 H 12 O 5
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).
Infobox references
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 .[1] E number E310 .
Description [ edit ]
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 [ edit ]
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] Steglich esterification with N,N'-diisopropylcarbodiimide and 4-dimethylaminopyridine , anhydrous addition of thionyl chloride , and Fischer esterification with various catalysts.[5]
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] 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 [ edit ]
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 [ edit ]
^ 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 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 .
R e t r i e v e d f r o m " https://en.wikipedia.org/w/index.php?title=Propyl_gallate&oldid=1228037844 " C a t e g o r i e s : ● A n t i o x i d a n t s ● G a l l a t e e s t e r s ● F o o d a n t i o x i d a n t s ● P r o p y l e s t e r s ● E - n u m b e r a d d i t i v e s H i d d e n c a t e g o r i e s : ● A r t i c l e s w i t h o u t K E G G s o u r c e ● E C H A I n f o C a r d I D f r o m W i k i d a t a ● E n u m b e r f r o m W i k i d a t a ● A r t i c l e s c o n t a i n i n g u n v e r i f i e d c h e m i c a l i n f o b o x e s ● C h e m b o x i m a g e s i z e s e t ● A r t i c l e s w i t h s h o r t d e s c r i p t i o n ● S h o r t d e s c r i p t i o n m a t c h e s W i k i d a t a
● T h i s p a g e w a s l a s t e d i t e d o n 9 J u n e 2 0 2 4 , a t 0 4 : 0 7 ( U T C ) . ● T e x t i s a v a i l a b l e u n d e r t h e C r e a t i v e C o m m o n s A t t r i b u t i o n - S h a r e A l i k e L i c e n s e 4 . 0 ;
a d d i t i o n a l t e r m s m a y a p p l y . B y u s i n g t h i s s i t e , y o u a g r e e t o t h e T e r m s o f U s e a n d P r i v a c y P o l i c y . W i k i p e d i a ® i s a r e g i s t e r e d t r a d e m a r k o f t h e W i k i m e d i a F o u n d a t i o n , I n c . , a n o n - p r o f i t o r g a n i z a t i o n . ● P r i v a c y p o l i c y ● A b o u t W i k i p e d i a ● D i s c l a i m e r s ● C o n t a c t W i k i p e d i a ● C o d e o f C o n d u c t ● D e v e l o p e r s ● S t a t i s t i c s ● C o o k i e s t a t e m e n t ● M o b i l e v i e w
