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Details

Stereochemistry ABSOLUTE
Molecular Formula C15H14O9S
Molecular Weight 370.3329
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of EPICATECHIN-5-SULFATE

SMILES

c1cc(c(cc1[C@]2([H])[C@@]([H])(Cc3c(cc(cc3OS(=O)(=O)O)O)O2)O)O)O

InChI

InChIKey=MWSSRHFQMROXGK-IUODEOHRSA-N
InChI=1S/C15H14O9S/c16-8-4-13-9(14(5-8)24-25(20,21)22)6-12(19)15(23-13)7-1-2-10(17)11(18)3-7/h1-5,12,15-19H,6H2,(H,20,21,22)/t12-,15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C15H14O9S
Molecular Weight 370.3329
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Epicatechin-5-Sulfate is a metabolite of epicatechin. It is patented for inclusion in food formulations intended for weight loss, and treatment of diabetes.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Identification of O-methyl-(-)-epicatechin-O-sulphate metabolites by mass-spectrometry after O-methylation with trimethylsilyldiazomethane.
2012 Jul 6
Absorption, metabolism, distribution and excretion of (-)-epicatechin: A review of recent findings.
2018 Jun
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Epicatechin-5-Sulfate is patented for inclusion in food compositions intended to be used for weight loss, and treatment of diabetes. The patent suggests a concentration of at least 0.01 mg/g of the food product.
Route of Administration: Oral
Human hepatocellular carcinoma HepG2 and human cervix adenocarcinoma HeLa cells were grown in Ham's F-12 medium supplemented with 7% fetal bovine serum at 37 deg-C in a 5% CO2 atmosphere. Cells were incubated with 10 micro-M of epicatechin sulfate for 48 hours. Cells cultures were assayed for RNA content and content of nuclear extracts. Epicatechin sulfate was found to induce ApoAI transcription through Site B.
Substance Class Chemical
Created
by admin
on Sat Jun 26 07:46:38 UTC 2021
Edited
by admin
on Sat Jun 26 07:46:38 UTC 2021
Record UNII
8T66C0D002
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPICATECHIN-5-SULFATE
Common Name English
(-)-EPICATECHIN 5-SULFATE
Common Name English
2H-1-BENZOPYRAN-3,5,7-TRIOL, 2-(3,4-DIHYDROXYPHENYL)-3,4-DIHYDRO-, 5-(HYDROGEN SULFATE), (2R,3R)-
Common Name English
(2R,3R)-2-(3,4-DIHYDROXYPHENYL)-3,7-DIHYDROXYCHROMAN-5-YL HYDROGEN SULFATE
Systematic Name English
((2R,3R)-2-(3,4-DIHYDROXYPHENYL)-3,7-DIHYDROXY-3,4-DIHYDRO-2H-CHROMEN-5-YL) HYDROGEN SULFATE
Systematic Name English
EPICATECHIN 5-O-SULPHATE
Common Name English
Code System Code Type Description
FDA UNII
8T66C0D002
Created by admin on Sat Jun 26 07:46:38 UTC 2021 , Edited by admin on Sat Jun 26 07:46:38 UTC 2021
PRIMARY
PUBCHEM
71579119
Created by admin on Sat Jun 26 07:46:38 UTC 2021 , Edited by admin on Sat Jun 26 07:46:38 UTC 2021
PRIMARY
CAS
1194377-44-0
Created by admin on Sat Jun 26 07:46:38 UTC 2021 , Edited by admin on Sat Jun 26 07:46:38 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE LESS ACTIVE
FRAP (ferric reducing ability of plasma) assay; Unit: TEAC (Trolox equivalent antioxidant capacity)- mM-Trolox equivalent/mM; epicatechin was 1.34
IN-VITRO