Skip to Content
Merck
All Photos(1)

Key Documents

04646

Sigma-Aldrich

Hamamelitannin

≥98.0% (HPLC)

Synonym(s):

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

Sign Into View Organizational & Contract Pricing


About This Item

Empirical Formula (Hill Notation):
C20H20O14
CAS Number:
Molecular Weight:
484.36
EC Number:
MDL number:
UNSPSC Code:
41116107
PubChem Substance ID:
NACRES:
NA.25

Quality Level

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

Looking for similar products? Visit Product Comparison Guide

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

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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
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

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service