hamamelitannin

2-O-((galloyloxy)methyl)-D-ribose 5-gallate

CAS: 469-32-9 C20 H20 O14 MW: 484.36820000

Identification

Namehamamelitannin
IUPAC[4-formyl-2,3,4-trihydroxy-5-(3,4,5-trihydroxybenzoyl)oxypentyl] 3,4,5-trihydroxybenzoate
CAS Number469-32-9
EINECS207-416-3
FDA UNIIZ4320A2K26
Molecular FormulaC20 H20 O14
Molecular Weight484.36820000
MDL NumberMFCD00017418

Regulatory

Physical Properties

Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 948.70 °C. @ 760.00 mm Hg (est)
Flash Point 626.00 °F. TCC ( 330.00 °C. ) (est)
logP (o/w) 3.120 (est)
Soluble in water, 1.356e+004 mg/L @ 25 °C (est)

No sensory data available

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for hamamelitannin usage levels up tonot for fragrance use.
Recommendation for hamamelitannin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

chestnut sweet chestnut witch hazel

Synonyms

[4- formyl-2,3,4-trihydroxy-5-(3,4,5-trihydroxybenzoyl)oxypentyl] 3,4,5-trihydroxybenzoate 2-O-(( galloyloxy)methyl)-D-ribose 5-gallate pentose, 2-C-[[(3,4,5-trihydroxybenzoyl)oxy]methyl]-, 5-(3,4,5-trihydroxybenzoate) 5-O-(3,4,5- trihydroxybenzoyl)-2-C-{[(3,4,5-trihydroxybenzoyl)oxy]methyl}pentose PubMed: Tannins from Hamamelis virginiana bark extract: characterization and improvement of the antiviral efficacy against influenza A virus and human papillomavirus. PubMed: In vivo antibiofilm effect of cerium, chitosan and hamamelitannin against usual agents of catheter-related bloodstream infections. PubMed: Cerium, chitosan and hamamelitannin as novel biofilm inhibitors? PubMed: Hamamelitannin from witch hazel (Hamamelis virginiana) displays specific cytotoxic activity against colon cancer cells. PubMed: Inhibitors of autoactivation of plasma hyaluronan-binding protein (factor VII activating protease). PubMed: Quorum sensing inhibitors increase the susceptibility of bacterial biofilms to antibiotics in vitro and in vivo. PubMed: Impact of thermal processing on the activity of gallotannins and condensed tannins from Hamamelis virginiana used as functional ingredients in seafood. PubMed: Suppression of biofilm related, device-associated infections by staphylococcal quorum sensing inhibitors. PubMed: Discovery of a quorum-sensing inhibitor of drug-resistant staphylococcal infections by structure-based virtual screening. PubMed: Determination of hamamelitannin, catechins and gallic acid in witch hazel bark, twig and leaf by HPLC. PubMed: Genotoxic and antigenotoxic effects of catechin and tannins from the bark of Hamamelis virginiana L. in metabolically competent, human hepatoma cells (Hep G2) using single cell gel electrophoresis. PubMed: Peroxynitrite scavenging activity of herb extracts. PubMed: Hamamelitannin from Hamamelis virginiana inhibits the tumour necrosis factor-alpha (TNF)-induced endothelial cell death in vitro. PubMed: Inhibitory effects of tetragalloylglucose and digalloylhamamelose on adhesion and in vitro invasion of mouse lung carcinoma cells. PubMed: Dual inhibitory activities of tannins from Hamamelis virginiana and related polyphenols on 5-lipoxygenase and lyso-PAF: acetyl-CoA acetyltransferase. PubMed: Antiviral and antiphlogistic activities of Hamamelis virginiana bark. PubMed: Protective activity of hamamelitannin on cell damage of murine skin fibroblasts induced by UVB irradiation. PubMed: Peroxyl radical scavenging activities of hamamelitannin in chemical and biological systems. PubMed: Protective activity of hamamelitannin on cell damage induced by superoxide anion radicals in murine dermal fibroblasts. PubMed: Activation of N-nitrosodialkylamines to mutagens by a metalloporphyrin/oxidant model system for cytochrome P450. PubMed: Novel Galloylhamameloses from Hamamelis virginiana1. PubMed: Evaluation of superoxide scavenging activities of hamamelis extract and hamamelitannin. PubMed: Tannins from Hamamelis virginiana: identification of proanthocyanidins and hamamelitannin quantification in leaf, bark, and stem extracts.