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(−)-Epicatechin - ≥90% (HPLC), high purity , CAS No.490-46-0, Agonist of TAS2R39

Moligand™
≥90%(HPLC)

CAS#: 490-46-0
Formula: C₁₅H₁₄O₆
Molecular Weight: 290.27
Beilstein Registry Number: 92760
EC Number: 207-710-1
PubChem CID: 72276

Item Number

E432751

Grouped product items
SKU	Size	Availability	Price	Qty
E432751-1g	1g	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$422.90
E432751-5g	5g	Available within 8-12 weeks(?) Production requires sourcing of materials. We appreciate your patience and understanding.	$1,918.90

Basic Description

Synonyms	(-)-Epicatechin\|Epicatechin\|490-46-0\|L-Epicatechin\|(-)-Epicatechol\|Epicatechol\|l-Acacatechin\|epi-Catechin\|epi-Catechol\|(2R,3R)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol\|l-Epicatechol\|(-)epicatechin\|(2R,3R)-(-)-Epicatechin\|(2R,3R)-2-(3,4-dihydroxyphenyl)-
Specifications & Purity	Moligand™, ≥90%(HPLC)
Biochemical and Physiological Mechanisms	Epicatechin enhances the skeletal muscle structure in heart failure patients and minimizes cardiometabolic risks. It can be used for treating sarcopenia. Epicatechin reduces myostatin and β-galactosidase and increases the level of markers of muscle growth
Grade	Moligand™
Action Type	AGONIST
Mechanism of action	Agonist of TAS2R39
Product Description	Gene Information human ... BACE1(23621), CYP1A2(1544) (−)-Epicatechin (EC) belongs to the group of flavanols and is abundantly present in cacao and cacao products. The chemical structure of EC includes an oxygenated heterocycle with a 4-hydroxyl group linked with two aromatic rings. Application (−)-Epicatechin (EC) has been used: as an antioxidant to downregulate nicotinamide adenine dinucleotide phosphate hydrogen (NADPH) oxidase and improve insulin sensitivity in in vivo (high fat-fed mice) and in vitro (HepG2 cells) studies to study its effect on blood pressure, nitric oxide synthase (NOS) activity and anxiety-like behavior on borderline hypertensive rat (BHR) models to test its effect on neuronal survival in the hippocampus of middle-aged rats on swimming training, under oxidative stress to study its antioxidant activity in dark chocolate as a characteristic compound in polyphenols analysis

Names and Identifiers

IUPAC Name	(2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
INCHI	InChI=1S/C15H14O6/c16-8-4-11(18)9-6-13(20)15(21-14(9)5-8)7-1-2-10(17)12(19)3-7/h1-5,13,15-20H,6H2/t13-,15-/m1/s1
InChi Key	PFTAWBLQPZVEMU-UKRRQHHQSA-N
Canonical SMILES	C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O
Isomeric SMILES	C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)O)O)O
WGK Germany	3
RTECS	KB3745000
Alternate CAS	490-46-0,17334-50-8
PubChem CID	72276
MeSH Entry Terms	(+)-Catechin;(+)-Cyanidanol;(+)-Cyanidanol-3;(-)-Epicatechin;(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol;2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-cis)-;3,3',4',5,7-Flavanpentol;Catechin;Catechinic Acid;Catechuic Acid;
Molecular Weight	290.27
Beilstein	92760

Certificates

Certificate of Analysis(COA)

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Chemical and Physical Properties

Specific Rotation[α]	-62° (C=0.1,MeOH)
Melt Point(°C)	240°C

Safety and Hazards(GHS)

Pictogram(s)	GHS07
Signal	Warning
Hazard Statements	H315:Causes skin irritation H319:Causes serious eye irritation H335:May cause respiratory irritation
Precautionary Statements	P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present and easy to do - continue rinsing. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P271:Use only outdoors or in a well-ventilated area. P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing. P403+P233:Store in a well-ventilated place. Keep container tightly closed. P362+P364:Take off contaminated clothing and wash it before reuse. P264+P265:Wash hands [and …] thoroughly after handling. Do not touch eyes. P337+P317:If eye irritation persists: Get medical help. P332+P317:If skin irritation occurs: Get medical help. P319:Get medical help if you feel unwell.
WGK Germany	3
RTECS	KB3745000

References

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61. Sansa Dutta,Amit Basak,Swagata Dasgupta. (2010-08-10) Synthesis and ribonuclease A inhibition activity of resorcinol and phloroglucinol derivatives of catechin and epicatechin: Importance of hydroxyl groups.. Bioorganic & medicinal chemistry, 18 ((17)): (6538-6546). [PMID:20692173]
62. Cornelia Braicu,Claudia D Gherman,Alexandru Irimie,Ioana Berindan-Neagoe. (2013-05-08) Epigallocatechin-3-Gallate (EGCG) inhibits cell proliferation and migratory behaviour of triple negative breast cancer cells.. Journal of nanoscience and nanotechnology, 13 ((1)): (632-637). [PMID:23646788]
63. Takahiro Kochi,Masahito Shimizu,Daishi Terakura,Atsushi Baba,Tomohiko Ohno,Masaya Kubota,Yohei Shirakami,Hisashi Tsurumi,Takuji Tanaka,Hisataka Moriwaki. (2013-08-29) Non-alcoholic steatohepatitis and preneoplastic lesions develop in the liver of obese and hypertensive rats: suppressing effects of EGCG on the development of liver lesions.. Cancer letters, 342 ((1)): (60-69). [PMID:23981577]
64. Job D F Inacio,Marilene M Canto-Cavalheiro,Elmo E Almeida-Amaral. (2013-10-11) In vitro and in vivo effects of (-)-epigallocatechin 3-O-gallate on Leishmania amazonensis.. Journal of natural products, 76 ((10)): (1993-1996). [PMID:24106750]
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(−)-Epicatechin - ≥90% (HPLC), high purity , CAS No.490-46-0, Agonist of TAS2R39

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