theaflavine
5H-benzocyclohepten-5-one, 1,8-bis[(2R,3R)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-2-yl]-3,4,6-trihydroxy-
Identification
| Name | theaflavine |
| CAS Number | 4670-05-7 |
| FDA UNII | 1IA46M0D13 |
| Molecular Formula | C29 H24 O12 |
| Molecular Weight | 564.50068000 |
| MDL Number | MFCD03427500 |
| Nikkaji Number | J277.684G |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 1003.90 °C. @ 760.00 mm Hg (est) |
| Flash Point | 638.00 °F. TCC ( 336.50 °C. ) (est) |
| logP (o/w) | 1.165 (est) |
| Soluble in | water, 44.99 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | intraperitoneal-mouse LD50 562 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for theaflavine usage levels up to | not for fragrance use. |
| Recommendation for theaflavine flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
5H-
benzocyclohepten-5-one, 1,8-bis[(2R,3R)-3,4-dihydro-3,5,7-trihydroxy-2H-1-benzopyran-2-yl]-3,4,6-trihydroxy-
theaflavin derivative
3,4,6-
trihydroxy-1,8-bis-((2R,3R)-3,5,7-trihydroxy-chroman-2-yl)-benzocyclohepten-5-one
3,4,6-
trihydroxy-1,8-bis[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]-5H-benzo[7]annulen-5-one
3,4,5-
trihydroxy-1,8-bis[(2R,3R)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-2-yl]benzo[7]annulen-6-one
1,8-bis(3-a,5,7-
trihydroxy-2-a-chromanyl)-5H-benzocyclohepten-5-one
PubMed:
Theaflavins enhance intestinal barrier of Caco-2 Cell monolayers through the expression of AMP-activated protein kinase-mediated Occludin, Claudin-1, and ZO-1.
PubMed:
The microbiota is essential for the generation of black tea theaflavins-derived metabolites.
PubMed:
Black tea polyphenols inhibit tumor proteasome activity.
PubMed:
Oxidative cascade reactions yielding polyhydroxy-theaflavins and theacitrins in the formation of black tea thearubigins: evidence by tandem LC-MS.
PubMed:
Theaflavins extracted from black tea inhibit airway mucous hypersecretion induced by cigarette smoke in rats.
PubMed:
Increase of theaflavin gallates and thearubigins by acceleration of catechin oxidation in a new fermented tea product obtained by the tea-rolling processing of loquat ( Eriobotrya japonica ) and green tea leaves.
PubMed:
Theaflavins from black tea, especially theaflavin-3-gallate, reduce the incorporation of cholesterol into mixed micelles.
PubMed:
PCR differential display-based identification of regulator of G protein signaling 10 as the target gene in human colon cancer cells induced by black tea polyphenol theaflavin monogallate.
PubMed:
Radical-scavenging abilities and antioxidant properties of theaflavins and their gallate esters in H2O2-mediated oxidative damage system in the HPF-1 cells.
PubMed:
Characteristics of catechin- and theaflavin-mediated cardioprotection.
PubMed:
Theaflavin-3-gallate and theaflavin-3'-gallate, polyphenols in black tea with prooxidant properties.
PubMed:
Combination of HSCCC and Sephadex LH-20 methods An approach to isolation and purification of the main individual theaflavins from black tea.
PubMed:
Modulation of the oxidative stress and nuclear factor kappaB activation by theaflavin 3,3'-gallate in the rats exposed to cerebral ischemia-reperfusion.
PubMed:
alpha-Glucosidase inhibitory profile of catechins and theaflavins.
PubMed:
Inhibitory effects of black tea theaflavin derivatives on 12-O-tetradecanoylphorbol-13-acetate-induced inflammation and arachidonic acid metabolism in mouse ears.
PubMed:
[Studies on antioxidant constituents from black tea].
PubMed:
Cancer prevention by tea polyphenols is linked to their direct inhibition of antiapoptotic Bcl-2-family proteins.
PubMed:
Differential effects of theaflavin monogallates on cell growth, apoptosis, and Cox-2 gene expression in cancerous versus normal cells.
PubMed:
Effect of black and green tea polyphenols on c-jun phosphorylation and H(2)O(2) production in transformed and non-transformed human bronchial cell lines: possible mechanisms of cell growth inhibition and apoptosis induction.
PubMed:
Suppression of extracellular signals and cell proliferation by the black tea polyphenol, theaflavin-3,3'-digallate.
PubMed:
An in vitro study of theaflavins extracted from black tea to neutralize bovine rotavirus and bovine coronavirus infections.
PubMed:
Inhibition of phorbol ester tumor promoter 12-O-tetradecanoylphorbol-13-acetate-caused inflammatory responses in SENCAR mouse skin by black tea polyphenols.
PubMed:
The antioxidant properties of theaflavins and their gallate esters--radical scavengers or metal chelators?
PubMed:
Prevention of heterocyclic amine formation by tea and tea polyphenols.