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Safety Information

04646

Sigma-Aldrich

Hamamelitannin

≥98.0% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C20H20O14
CAS Number:
469-32-9
Molecular Weight:
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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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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

04646-1MG-F:
04646-BULK-F:
04646-5MG-F:
04646-VAR-F:

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Certificates of Analysis (COA)

Lot/Batch Number
BCCB2908
BCBW0711
BCBT0643
BCBP7861V
BCBN3412V

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E Okochi et al.
Biological & pharmaceutical bulletin, 18(1), 49-52 (1995-01-01)
N-Nitrosodialkylamines are environmental alkylating carcinogens which are metabolically activated to alpha-hydroxy nitrosamines by cytochrome P450. The precise mechanism of their activation is not well understood, and a simplified chemical model for cytochrome P450 as a non-enzymatic system is useful for
Hye Rhi Choi et al.
Phytotherapy research : PTR, 16(4), 364-367 (2002-07-12)
Peroxynitrite (ONOO(-)) is a cytotoxicant with strong oxidizing properties toward various cellular constituents, including sulphydryls, lipids, amino acids and nucleotides and can cause cell death, lipid peroxidation, carcinogenesis and aging. The aim of this study was to characterize ONOO(-) scavenging
Andreas Dauer et al.
Phytochemistry, 63(2), 199-207 (2003-04-25)
The genotoxic and antigenotoxic activities of catechin, hamamelitannin and two proanthocyanidin fractions prepared from the bark of Hamamelis virginiana L. were investigated in a human derived, metabolically competent hepatoma cell line (Hep G2) using single cell gel electrophoresis (SCGE) for
L Cobrado et al.
The Journal of antimicrobial chemotherapy, 67(5), 1159-1162 (2012-02-10)
The colonization of indwelling medical devices and subsequent biofilm formation represents a global challenge since it promotes the persistence of infection and contributes to antimicrobial resistance. The aim of this study was to determine the antimicrobial activity of cerium, chitosan
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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