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W294705

Sigma-Aldrich

Propyl gallate

≥98%, FCC

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Synonym(s):
3,4,5-Trihydroxybenzoic acid propyl ester
Linear Formula:
3,4,5-(HO)3C6H2CO2CH2CH2CH3
CAS Number:
121-79-9
Molecular Weight:
212.20
FEMA Number:
2947
Beilstein:
1877976
EC Number:
204-498-2
MDL number:
MFCD00002196
eCl@ss:
39024506
PubChem Substance ID:
24901412
NACRES:
NA.21

biological source

synthetic

Quality Level

400

grade

Fragrance grade
Halal
Kosher

Agency

follows IFRA guidelines

reg. compliance

EU Regulation 1223/2009
EU Regulation 1334/2008 & 178/2002
EU Regulation 178/2002
FCC
FDA 21 CFR 172.615
FDA 21 CFR 175.125
FDA 21 CFR 175.300
FDA 21 CFR 175.380
FDA 21 CFR 175.390
FDA 21 CFR 184.1660

Assay

≥98%

mp

146-149 °C (lit.)

application(s)

flavors and fragrances

Documentation

see Safety & Documentation for available documents

food allergen

no known allergens

fragrance allergen

no known allergens

Organoleptic

odorless

SMILES string

CCCOC(=O)c1cc(O)c(O)c(O)c1

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

InChI key

ZTHYODDOHIVTJV-UHFFFAOYSA-N

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General description

Propyl gallate is mainly used as an antioxidant for edible fats and vegetable oils. It occurs naturally in the pods of tara tree.

Application

Used as an anti-fade reagent in fluorescence microscopy to reduce photobleaching of fluorescent probes such as rhodamine and fluorescein.

Biochem/physiol Actions

An antioxidant that exhibits antimicrobial activity. Propyl gallate has been reported to be an effective antioxidant-based hepatoprotector, both in vitro and in vivo. It has also been shown to prevent neuronal apoptosis and block the death of neurons exposed to FeSO4/GA as well as partially protect endothelial cells against TNF-induced apoptosis.
An antioxidant that exhibits antimicrobial activity. Propyl gallate has been reported to be an effective antioxidant-based hepatoprotector, both in vitro and in vivo. It has also been shown to prevent neuronal apoptosis and block the death of neurons exposed to FeSO4/GA as well as partially protect endothelial cells against TNF-induced apoptosis. However, propyl gallate induced single strand breaks in DNA at concentrations higher than 0.25 μM when it was combined with copper concentrations at 5 μM and above. Another report, however, found that incubation of isolated rat hepatocytes with propyl gallate at concentrations of >1 mM induced cell killing, whereas, a lower concentration of propyl gallate > 0.5 mM resulted in a ladder formation of soluble low-molecular weight DNA fragments, characteristic of apoptosis.

Reconstitution

Prepare a 0.1M solution in glycerol:PBS (9:1)

Disclaimer

For R&D or non-EU Food use. Not for retail sale.

Signal Word

Danger

Hazard Statements

H302 - H317 - H318 - H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Eye Dam. 1 - Skin Sens. 1

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 2

Flash Point(F)

368.6 °F - closed cup

Flash Point(C)

187 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Antioxidants for food fats and oils.
Sherwin ER.
Journal of the American Oil Chemists' Society, 49(8), 468-472 (1972)
A review on DNA interaction with synthetic phenolic food additives.
Dolatabadi JEN & Kashanian S.
Food Research International, 43(5), 1223-1230 (2010)
Oxidation and antioxidants in fat and oil processing.
Sherwin ER.
Journal of the American Oil Chemists' Society, 55(11), 809-814 (1978)
Matloob Ahmad et al.
European journal of medicinal chemistry, 45(2), 698-704 (2009-12-08)
A series of potential anti-oxidant and anti-bacterial N'-arylmethylidene-2-(3,4-dimethyl-5,5-dioxidopyrazolo[4,3-c][1,2]benzothiazin-2(4H)-yl)acetohydrazides was synthesized in a facile way starting from commercially available saccharine. 3,4-Dimethyl-2,4-dihydropyrazolo[4,3-c][1,2]benzothiazine 5,5-dioxide was obtained by ring expansion of 2-(2-oxopropyl)-1,2-benzisothiazol-3(2H)-one 1,1-dioxide followed by N-methylation and cyclization with hydrazine using ultrasonic irradiation. N-alkylation
Yasunobu Kawano et al.
Resuscitation, 83(2), 249-252 (2011-08-02)
The present study was conducted to assess the effects of intraperitoneal administration of n-propyl gallate (PG) on hippocampal neuronal survival after forebrain ischemia. Forty male Sprague-Dawley rats were randomly assigned to one of 6 groups. Animals in the PG-I-10, PG-I-8
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