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04646

Sigma-Aldrich

Hamamelitannin

≥98.0% (HPLC)

Synonyma:

2-C-(Hydroxymethyl)-D-ribofuranose 2′,5-digallate, Hamamelofuranose 2′,5-digallate

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About This Item

Empirický vzorec (Hillův zápis):
C20H20O14
Číslo CAS:
469-32-9
Molekulová hmotnost:
484.36
EC Number:
207-416-3
MDL number:
MFCD00017418
UNSPSC Code:
41116107
PubChem Substance ID:
329747966
NACRES:
NA.25

Quality Level

100

assay

≥98.0% (HPLC)

form

powder or crystals

application(s)

food and beverages
metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

2-8°C

SMILES string

OC1O[C@H](COC(=O)c2cc(O)c(O)c(O)c2)[C@@H](O)[C@]1(O)COC(=O)c3cc(O)c(O)c(O)c3

InChI

1S/C20H20O14/c21-9-1-7(2-10(22)14(9)25)17(28)32-5-13-16(27)20(31,19(30)34-13)6-33-18(29)8-3-11(23)15(26)12(24)4-8/h1-4,13,16,19,21-27,30-31H,5-6H2/t13-,16-,19?,20-/m1/s1

InChI key

FEPAFOYQTIEEIS-IZUGRSKYSA-N

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Související kategorie

General description

Hamamelitanninis a tannin derived from the bark and leaves of Hamamelis virginiana(witch hazel).

Application

Hamamelitannin can be used to study chromatography, aromatics, esters, hamamelis, heterocyclics, natural compounds, phenols, phytopharma standards, polyhydroxy compounds, and tannins. It also significantly reduces biofilm metabolic activity of the following bacteria: Staphylococcus epidermidis, Staphylococcus aureus, Acinetobacter baumannii, and Candida albicans strains. Hamamelitannin displays specific cytotoxic activity against colon cancer cells. It has been used in a study to determine that quorum-sensing inhibitors increase the success of antibiotic treatment by increasing the susceptibility of bacterial biofilms and/or by increasing host survival following infection.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Osvědčení o analýze (COA)

Lot/Batch Number
BCCJ9967
BCCB2908
BCBW0711
BCBT0643

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Madanahally D Kiran et al.
Molecular pharmacology, 73(5), 1578-1586 (2008-03-04)
Staphylococci are a major health threat because of increasing resistance to antibiotics. An alternative to antibiotic treatment is preventing virulence by inhibition of bacterial cell-to-cell communication using the quorum-sensing inhibitor RNAIII-inhibiting peptide (RIP). In this work, we identified 2',5-di-O-galloyl-d-hamamelose (hamamelitannin)
Huafu Wang et al.
Journal of pharmaceutical and biomedical analysis, 33(4), 539-544 (2003-11-19)
An HPLC method for the determination of hamamelitannin, catechins and gallic acid in witch hazel bark, twig and leaf has been developed. The separation system consisted of a C18 reversed-phase column, a gradient elution system of methanol/water and orthophosphoric acid
H Masaki et al.
Free radical research, 22(5), 419-430 (1995-05-01)
The antioxidative activities of hamamelitannin (2',5-di-O-galloyl-hamamelose), gallic acid and dl-alpha-tocopherol against lipid peroxyl radicals were evaluated in chemical and biological systems. The peroxyl radical scavenging activity was evaluated by electron spin resonance (ESR) method in which both spin-trapping and direct
Akram M Salam et al.
Current opinion in microbiology, 45, 189-194 (2018-09-16)
The continued spread of antimicrobial resistance represents one of the most serious infectious disease threats to global health. There is consensus that a key component of addressing this threat is to replenish the waning pipeline of antimicrobials, with attention being
K Saeki et al.
Planta medica, 65(3), 227-229 (1999-05-08)
Tetragalloylglucose (TgG) and digalloylhamamelose (DgH) were found to inhibit adhesion to and invasion through Matrigel of mouse Lewis lung carcinoma LL2-Lu3 cells, which are highly metastatic. TgG inhibited matrix metalloproteinases (MMPs) from the tumor cells like (-)-epigallocatechin gallate, whereas DgH
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