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48660

Sigma-Aldrich

Lauryl gallate

antioxidant, ≥99.0% (HPLC)

Synonym(s):

Dodecyl gallate

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About This Item

Empirical Formula (Hill Notation):
C19H30O5
CAS Number:
1166-52-5
Molecular Weight:
338.44
Beilstein:
2701981
EC Number:
214-620-6
MDL number:
MFCD00002195
UNSPSC Code:
12352100
PubChem Substance ID:
57651156
NACRES:
NA.22

Assay

≥99.0% (HPLC)

form

solid

mp

94-97 °C (lit.)

SMILES string

CCCCCCCCCCCCOC(=O)c1cc(O)c(O)c(O)c1

InChI

1S/C19H30O5/c1-2-3-4-5-6-7-8-9-10-11-12-24-19(23)15-13-16(20)18(22)17(21)14-15/h13-14,20-22H,2-12H2,1H3

InChI key

RPWFJAMTCNSJKK-UHFFFAOYSA-N

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Application

  • Properties of artificial phospholipid membranes containing lauryl gallate or cholesterol: This study explores how lauryl gallate affects membrane structure, impacting its biological functions (Jurak et al., 2018).
  • Potential of Lauryl Gallate as Stability and Recyclability Improver of Poly (Butylene succinate-co-adipate): Lauryl gallate enhances the stability and recyclability of polyesters, important for sustainable materials (Rossi et al., 2024).
  • Lauryl Gallate Activity and Streptococcus mutans: The study evaluates the antibacterial effects of lauryl gallate against Streptococcus mutans, showing significant biofilm reduction and gene expression impact (Gabe et al., 2020).
  • Dodecyl gallate as a pro-ecological antioxidant for food packing materials: This research investigates the use of lauryl gallate as a green antioxidant, enhancing the age-resistance of food packaging (Masek et al., 2014).

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Isao Kubo et al.
Bioorganic & medicinal chemistry, 11(4), 573-580 (2003-01-23)
Dodecyl (C(12)) gallate (3,4,5-trihydroxybenzoate) (1) was found to possess antibacterial activity specifically against Gram-positive bacteria, in addition to its potent antioxidant activity. The time-kill curve study indicates that this amphipathic gallate exhibits bactericidal activity against methicillin resistant Staphylococcus aureus (MRSA)
Isao Kubo et al.
Bioorganic & medicinal chemistry letters, 12(2), 113-116 (2002-01-05)
A series of alkyl gallates (3,4,5-trihydroxybenzoates) was found to show antibacterial activity against Gram-positive bacteria including methicillin resistant Staphylococcus aureus (MRSA) strains. For example, dodecyl (C(12)) gallate (1) exhibited bactericidal activity against MRSA ATCC 33591 strain with the minimum bactericidal
Annarica Calcabrini et al.
Carcinogenesis, 27(8), 1699-1712 (2006-04-21)
Lauryl gallate is an antioxidant food additive showing low toxicity to normal cells. Here, its antiproliferative effect has been studied on three human breast cancer cell lines: estrogen-dependent, wild-type p53, MCF7; estrogen-independent, non-functional p53, MDA-MB-231 and MCF7 ADR, which overexpresses
Isao Kubo et al.
Journal of agricultural and food chemistry, 50(12), 3533-3539 (2002-05-30)
Dodecyl (C12) gallate exhibits both potent chain-breaking and preventive antioxidant activity. The pyrogallol moiety is responsible for both activities. Dodecyl (lauryl) gallate prevents generation of superoxide radicals by xanthine oxidase, and this activity comes from its ability to inhibit the
Tae Joung Ha et al.
Journal of agricultural and food chemistry, 55(2), 446-451 (2007-01-18)
Dodecyl gallate inhibited the soybean lipoxygenase-1 (EC 1.13.11.12, type-1) catalyzed peroxidation of linoleic acid with an IC50 of 0.007 microM without being oxidized. The progress curves for enzyme reactions were recorded by both spectrophotometric and polarographic methods, and the inhibition
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