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

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Name:[4-formyl-2,3,4-trihydroxy-5-(3,4,5-trihydroxybenzoyl)oxypentyl] 3,4,5-trihydroxybenzoate
CAS Number: 469-32-9Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-416-3
FDA UNII: Z4320A2K26
MDL:MFCD00017418
XlogP3-AA:-1.30 (est)
Molecular Weight:484.36820000
Formula:C20 H20 O14
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Google Patents:Search
US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Hamamelitannin > 95%
Odor: characteristic
Use: Hamamelitannin can be used to study chromatography, aromatics, esters, hamamelis, heterocyclics, natural compounds, phenols, phytopharma standards, polyhydroxy compounds and tannins. It significantly reduces biofilm metabolic activity
ExtraSynthese
For experimental / research use only.
Hamamelitannin (HPLC) ≥95%
Santa Cruz Biotechnology
For experimental / research use only.
Hamamelitannin ≥98%
Sigma-Aldrich
For experimental / research use only.
Hamamelitannin ≥98.0% (HPLC)
 
Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for hamamelitannin usage levels up to:
 not for fragrance use.
 
Recommendation for hamamelitannin flavor usage levels up to:
 not for flavor use.
 
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :3081370
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
[4-formyl-2,3,4-trihydroxy-5-(3,4,5-trihydroxybenzoyl)oxypentyl] 3,4,5-trihydroxybenzoate
Chemidplus:0000469329
 
References:
 [4-formyl-2,3,4-trihydroxy-5-(3,4,5-trihydroxybenzoyl)oxypentyl] 3,4,5-trihydroxybenzoate
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):3081370
Pubchem (sid):135228486
 
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
HMDB (The Human Metabolome Database):HMDB33785
FooDB:FDB011943
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 chestnut sweet chestnut
Search Trop Picture
 witch hazel
Search Trop Picture
 
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
 

Articles:

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.
 
Notes:
cytotoxic from witch hazel (hamamelis virginiana). Isol. from Castanea sativa (sweet chestnut)
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