(3,4,5-Trihydroxy-6-oxo-6h-benzo[7]annulene-1,8-diyl)bis[(2r,3r)-5,7-dihydroxy-3,4-dihydro-2h-chromene-2,3-diyl] bis(3,4,5-trihydroxybenzoate)

HCID 467320

Notes Reactions

Substructure search Find similar structures

Basic information

CAS: 30462-35-2
Standard SMILES: O=C(O[C@@H]1Cc2c(O)cc(O)cc2O[C@@H]1c1cc(=O)c(O)c2c(O)c(O)cc([C@H]3Oc4cc(O)cc(O)c4C[C@H]3OC(=O)c3cc(O)c(O)c(O)c3)c2c1)c1cc(O)c(O)c(O)c1
InChIKey: ZEASWHWETFMWCV-ISBUVJFSSA-N
Molecular formula: C43H32O20
Average molar mass: 868.7 g/mol
Monoisotopic mass: 868.14869342

Names & identifiers

Preferred name: (3,4,5-Trihydroxy-6-oxo-6h-benzo[7]annulene-1,8-diyl)bis[(2r,3r)-5,7-dihydroxy-3,4-dihydro-2h-chromene-2,3-diyl] bis(3,4,5-trihydroxybenzoate)
IUPAC: [(2R,3R)-2-[1-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-3,4,5-trihydroxy-6-oxobenzo[7]annulen-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
English name: Theaflavin 3,3′-digallate
Molecular formula: C43H32O20
Molecular weight: 868.71

Names & synonyms

C43H32O20orb1220993orb1301797orb3139544AKOS040758746EBC-519718T5429(2R,2'R,3R,3'R)-2,2'-(3,4,5-Trihydroxy-6-oxo-6H-benzo[7]annulene-1,8-diyl)bis(5,7-dihydroxychroman-3,2-diyl) bis(3,4,5-trihydroxybenzoate)(2R,3R)-2-{1-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-3,4-dihydro-2H-1-benzopyran-2-yl]-3,4,6-trihydroxy-5-oxo-5H-benzo[7]annulen-8-yl}-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate(3,4,5-trihydroxy-6-oxo-6h-benzo[7]annulene-1,8-diyl)bis[(2r,3r)-5,7-dihydroxy-3,4-dihydro-2h-chromene-2,3-diyl] bis(3,4,5-trihydroxybenzoate)[(2R,3R)-2-[1-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-chroman-2-yl]-3,4,5-trihydroxy-6-oxo-benzo[7]annulen-8-yl]-5,7-dihydroxy-chroman-3-yl] 3,4,5-trihydroxybenzoateTFDG

Show more names

Theaflavin 3,3'-digallateTheaflavin 3,3'-di-O-gallatetheaflavin 3Theaflawin3.8-Gingerol Hplc8-GINGEROL, HPLC 98%Theaflavin 3,3’Theaflavin 3.3-diaallateTheaflavin 3,3’-Digallate

Database identifiers

CAS: 30462-35-2
PubChem CID: 467320
DTXSID: DTXSID20332815
ChEMBL: CHEMBL434864
Nikkaji: J92.503I

Properties

Computed structural properties

XLogP: 3
Topological polar surface area: 351 Å²
Hydrogen bond donors: 13
Hydrogen bond acceptors: 20
Rotatable bonds: 8
Heavy atoms: 63
Formal charge: 0
Complexity: 1,950

Experimental & physicochemical properties

Collision Cross Section268.4 Å² [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point: 226 · 226~230℃
Boiling point: 1352.6 · 1352.6±65.0 °C(Predicted)
Density: 1.97 · 1.97±0.1 g/cm3(Predicted)
storage temp.: -20 °C, · Store at -20°C, sealed storage, away from moisture and light
solubility: 41.67 mg/mL · DMSO : 41.67 mg/mL (47.97 mM; Need ultrasonic)
form: Solid
pka: 6.55 · 6.55±0.20(Predicted)
color: Red-purple
InChIKey: ZEASWHWETFMWCV-ISBUVJFSSA-N
SMILES: O=C1C(C(O)=C(O)C=C2[C@@H]3[C@H](OC(C4=CC(O)=C(O)C(O)=C4)=O)CC(C(O)=CC(O)=C5)=C5O3)=C2C=C([C@H]6OC(C=C(O)C=C7O)=C7C[C@H]6OC(C8=CC(O)=C(O)C(O)=C8)=O)C=C1O
CAS DataBase Reference: 30462 · 30462-35-2
FDA UNII: 0 IJB138K · LB0IJB138K
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
WGK Germany: 3 · 3
HS Code: 29329990 · 29329990

Safety & regulation

Safety data

wgk: 3
hs_code: 29329990

Chemistry & industry

Applications · 4 items

DescriptionTheaflavin-3,3''-digallate (TFDG) is a major polyphenol found in black tea with diverse biological activities. It has antioxidant activity, inhibiting the formation of superoxide radicals, singlet oxygen, hydrogen peroxide, and hydroxyl radicals in vitro (IC50s = 26.7, 0.83, 0.39, and 25.07 μmol/L, respectively). It also reduces hydroxyl radical-induced damage to plasmid DNA. TFDG (12.5-50 μM) prevents LPS-induced release of TNF-α, IL-1β, and IL-6, expression of JNK and p38, and nuclear translocation of NF-κB in RAW 264.7 cells. In vivo, TFDG reduces serum levels of TNF-α, IL-1β, and IL-6 and decreases pulmonary edema, pulmonary congestion, and thickening of the alveolar wall in a mouse model of LPS-induced acute lung injury. It also inhibits osteoclast formation, polarization, and osteoclastic bone resorption in vitro and reduces titanium particle-induced bone erosion and the number of mature osteoclasts in mice in a dose-dependent manner.

UsesTheaflavin 3,3′-digallate may be used as an analytical reference standard for the quantification of the analyte in tea samples using high-performance liquid chromatography with tandem mass spectrometric detection.

UsesTheaflavin 3,3''-Digallate has been found to be an inhibitor against human pancreatic α-Amylase.

General DescriptionTheaflavin 3,3′-digallate is a theaflavin derivative, exhibiting antioxidative, anti-inflammatory, and anti-tumor activities. It is also associated with many beneficial health effects, including the prevention of cancer and heart disease.