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-

CAS: 4670-05-7 C29 H24 O12 MW: 564.50068000

Identification

Nametheaflavine
CAS Number4670-05-7
FDA UNII1IA46M0D13
Molecular FormulaC29 H24 O12
Molecular Weight564.50068000
MDL NumberMFCD03427500
Nikkaji NumberJ277.684G

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 Toxicityintraperitoneal-mouse LD50 562 mg/kg
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 theaflavine usage levels up tonot for fragrance use.
Recommendation for theaflavine flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

tea black tea tea leaf tea shoot

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.