Cas no 490-46-0 ((-)-Epicatechin)

(-)-Epicatechin is a naturally occurring flavonoid compound exhibiting antioxidant properties and potential health benefits. It has been shown to scavenge free radicals, modulate cellular signaling pathways, and influence gene expression, contributing to its purported therapeutic applications in cardiovascular disease prevention and neuroprotection.
(-)-Epicatechin structure
(-)-Epicatechin structure
Product Name:(-)-Epicatechin
CAS No:490-46-0
MF:C15H14O6
MW:290.2681
MDL:MFCD00075648
CID:37736
PubChem ID:24894538
Update Time:2025-10-21

(-)-Epicatechin Chemical and Physical Properties

Names and Identifiers

    • (2R,3R)-2-(3,4-Dihydroxyphenyl)chroman-3,5,7-triol
    • (-)-EPICATECHIN
    • (+)-EPICATECHIN
    • EPICATECHIN
    • EPICATECHIN, (-)-
    • EPICATECHIN, (+)-
    • CIS-2-[3,4-DIHYDROXYPHENYL]-3,4-DIHYDRO-2H-1-BENZOPYRAN-3,5,7-TRIOL
    • (-)-CIS-3,3',4',5,7-PENTAHYDROXYFLAVANE
    • CIS-3,3',4',5,7-PENTAHYDROXYFLAVANE
    • Epicatechin (EC)
    • (-)Epicatechin
    • (-)-EPICATECHIN CRYSTALLINE
    • (-)-Epicatechin, froM green tea
    • (?)-Epicatechin
    • (?)-Epicatechin
    • EPICATECHIN, (-)-(P) (AHP Verified)(REQUEST QUOTE)
    • EPICATECHIN, (-)-(RG)
    • L-Epicatechin
    • (-)-Epicatechin (EC)
    • (-)-Epicatechol
    • (?)-cis-3,3',4',5,7-Pentahydroxyflavane
    • (?)-Epicatechin,from green tea
    • (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol
    • epi-Catechin
    • 2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
    • (-)-Epicatechin;EC
    • l-Acacatechin
    • Epicatechol
    • l-Epicatechol
    • (2R,3R)-(-)-Epicatechin
    • epi-Catechol
    • Epicatechol, (-)-
    • 34PHS7TU43
    • PFTAWBLQPZVEMU-UKRRQHHQSA-N
    • (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol
    • (-)-(2R:3R)-5,7,3',4'-Tetrahydroxyflavan-3-ol
    • (-)-cis-Epicatechin
    • SCHEMBL12037486
    • Procyanidin trimer EEC
    • DTXSID001341556
    • (2R,3S)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol
    • ConMedNP.1817
    • ConMedNP.1816
    • ConMedNP.1815
    • ConMedNP.1814
    • (2S,3S)-3,3',4',5,7-pentahydroxyflavan
    • (+)-Catechol
    • (+)-(2R,3S)-5,7,3',4'-Tetrahydroxyflavan-3-ol
    • Dexcyanidanol
    • catechin L-form
    • SMR001233344
    • EC
    • (2R-trans)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-Benzopyran-3,5,7-triol
    • L-Catechin
    • MLS002154016
    • (-)-Catechin
    • (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1H-benzopyran-3,5,7-triol
    • Cianidanol
    • D-Catechol
    • Cyanidanol
    • Dataset-S1.4
    • Dataset-S1.5
    • D-Catechin
    • Catechin Ent-catechin
    • Teafuran 30A
    • MLSMR
    • (+)-3',4',5,7-Tetrahydroxy-2,3-trans-flavan-3-ol
    • (+)-Cyanidan-3-ol
    • ent-Catechin
    • Catechin
    • (-)-epi-catechin
    • (2R,3S)-Catechin
    • (2R,3S)-(+)-Catechin
    • Catechin-(+,-) hydrate
    • catechuic acid
    • (+)-Catechin
    • (+)-Cyanidanol
    • ent-Epicatechin
    • (2S,3S)-3',4',5,7-tetrahydroxyflavan-3-ol
    • Epicatechin (EC),98%
    • 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R-cis)-
    • (-)-Epicatechin, analytical standard
    • KBio2_003207
    • UNII-34PHS7TU43
    • EINECS 207-710-1
    • 28E
    • BDBM23417
    • AKOS015895981
    • O10053
    • DivK1c_006363
    • Spectrum_000159
    • Tox21_110101
    • Q-200001
    • C15H14O6
    • SMR000156230
    • Spectrum5_000929
    • CAS-154-23-4
    • NSC81161
    • Prestwick_203
    • KBio2_000639
    • NS00093637
    • alpha-catechin
    • KBioGR_001538
    • NCGC00017331-08
    • C09727
    • (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
    • L-Epicatechin ,(S)
    • DTXCID2025133
    • 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-, (2R,3R)-
    • HY-N0001
    • Lopac-C-1251
    • NSC 81161
    • NCGC00016415-04
    • SPECTRUM210206
    • NSC-81161
    • SDCCGMLS-0066927.P001
    • SCHEMBL19412
    • 1ST000539
    • 2-(3,4-Dihydroxyphenyl)-2,3,4-trihydro-3,5,7-trihydroxychromene
    • NCGC00015215-02
    • SMP1_000115
    • AC-14586
    • (2R,3R)-2-(3,4-Dihydroxyphenyl)-3,5,7-chromanetriol
    • DS-3358
    • LMPK12020003
    • BCBcMAP01_000224
    • NCGC00016415-01
    • Spectrum2_000675
    • MLS001304012
    • KBio2_005775
    • Spectrum4_000949
    • Tox21_110101_1
    • 490-46-0
    • KUC104404N
    • 2H-1-Benzopyran-3,5,7-triol, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-,(2R,3R)-
    • NCGC00015215-01
    • SpecPlus_000267
    • (-)-Epicatechin 1000 microg/mL in Acetone
    • (2R-cis)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
    • Q23050136
    • CHEBI:90
    • s4723
    • HMS1923M05
    • KBio3_001126
    • BP-30203
    • (-)-Epicatechin 1000 microg/mL in Acetonitrile
    • .alpha. Catechin
    • DB12039
    • CAS-490-46-0
    • ACon1_001106
    • L(-)-Epicatechin
    • GTPL12497
    • DTXSID4045133
    • (-)-epi catechin
    • NCGC00016415-02
    • Epicatechin, primary pharmaceutical reference standard
    • (-)-Epicatechin, >=98% (HPLC), from green tea
    • (-)-EPICATECHIN (CONSTITUENT OF MARITIME PINE) [DSC]
    • Oprea1_209947
    • 2,3-cis-epicatechin
    • CHEMBL583912
    • CAS-7295-85-4
    • SPBio_000769
    • BSPBio_001626
    • (-)-EPICATECHIN(EG) (CONSTITUENT OF POWDERED DECAFFEINATED GREEN TEA EXTRACT)
    • (-)-EPICATECHIN (CONSTITUENT OF MARITIME PINE)
    • KSC-10-144
    • (-)-Epicatechin, >=90% (HPLC)
    • L-EPICATECHIN [WHO-DD]
    • CF3BA0C2-DE1B-44AB-A4D3-800F017221BA
    • E1226
    • Spectrum3_000243
    • (2R,3R)-2-(3,4-dihydroxyphenyl)chromane-3,5,7-triol
    • KBio1_001307
    • 3,3',4',5,7-Pentahydroxyflavane
    • (-)-EPICATECHIN (USP-RS)
    • Epicatechin-(-)
    • CCG-38571
    • NCGC00016415-03
    • CS-3760
    • MLS001304152
    • (-)-EPICATECHIN (CONSTITUENT OF GRAPE SEEDS OLIGOMERIC PROANTHOCYANIDINS)
    • CCRIS 7097
    • cid_72276
    • KBioSS_000639
    • (-)-EPICATECHIN [USP-RS]
    • (-)-Epicatechin
    • MDL： MFCD00075648
    • 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
    • SMILES： O1C2=C([H])C(=C([H])C(=C2C([H])([H])[C@]([H])([C@@]1([H])C1C([H])=C([H])C(=C(C=1[H])O[H])O[H])O[H])O[H])O[H]
    • BRN： 92760

Computed Properties

  • Exact Mass: 290.07900
  • Monoisotopic Mass: 290.079
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 5
  • Hydrogen Bond Acceptor Count: 6
  • Heavy Atom Count: 21
  • Rotatable Bond Count: 1
  • Complexity: 364
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 2
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Molecular Weight: 290.27
  • Surface Charge: 0
  • Tautomer Count: 90
  • XLogP3: 0.4
  • Topological Polar Surface Area: 110

Experimental Properties

  • Color/Form: Powder
  • Density: 1.5930
  • Melting Point: 240?°C (dec.) (lit.)
  • Boiling Point: 630.4°C at 760 mmHg
  • Flash Point: 335°C
  • Refractive Index: 1.741
  • Solubility: 6.311e+004 mg/L @ 25 °C (est)
  • Water Partition Coefficient: Soluble in water or alcohol
  • PSA: 110.38000
  • LogP: 1.54610
  • Solubility: Not determined
  • Merck: 13,1912
  • λmax: 280(MeOH)(lit.)
  • Specific Rotation: -55～-65゜(D/20℃)(c=1,CH3OH)

(-)-Epicatechin Security Information

  • Symbol: GHS02 GHS07
  • Prompt：warning
  • Signal Word：Warning
  • Hazard Statement： H226,H315,H319,H335
  • Warning Statement： P261,P305+P351+P338
  • Hazardous Material transportation number：NONH for all modes of transport
  • WGK Germany：3
  • Hazard Category Code： 36/37/38
  • Safety Instruction： S26-S36
  • FLUKA BRAND F CODES：10-23
  • RTECS：KB3745000
  • Hazardous Material Identification： Xi
  • Safety Term：S26;S36
  • Risk Phrases：R36/37/38
  • Storage Condition：Powder -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month

(-)-Epicatechin Customs Data

  • HS CODE：29329990

(-)-Epicatechin Pricemore >>

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(-)-Epicatechin Production Method

(-)-Epicatechin Suppliers

Tiancheng Chemical (Jiangsu) Co., Ltd
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(CAS:490-46-0)L-Epicatechin
Order Number:LE10002;LE6541;LE2456283
Stock Status:in Stock
Quantity:25KG,200KG,1000KG
Purity:99%
Pricing Information Last Updated:Friday, 20 June 2025 12:02
Price ($):discuss personally
Amadis Chemical Company Limited
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(CAS:490-46-0)(-)-Epicatechin
Order Number:A871843
Stock Status:in Stock
Quantity:100g
Purity:99%
Pricing Information Last Updated:Friday, 30 August 2024 09:31
Price ($):545.0
Suzhou Senfeida Chemical Co., Ltd
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(CAS:490-46-0)L-Epicatechin
Order Number:sfd1508
Stock Status:in Stock
Quantity:200kg
Purity:99.9%
Pricing Information Last Updated:Friday, 19 July 2024 14:32
Price ($):discuss personally
Hubei Cuiyuan Biotechnology Co.,Ltd
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(CAS:490-46-0)Epicatechin
Order Number:CRN0059
Stock Status:in stock
Quantity:5mg/20mg/50mg
Purity:≥98%
Pricing Information Last Updated:Friday, 14 March 2025 10:55
Price ($):

(-)-Epicatechin Spectrogram

1H NMR 300 MHz DMSO
1H NMR
13C NMR
13C NMR

(-)-Epicatechin Related Literature

Related Categories

Additional information on (-)-Epicatechin

Introduction to (-)-Epicatechin (CAS No. 490-46-0)

Epicatechin, a naturally occurring flavonoid, is a derivative of catechin and is widely recognized for its significant biological activities. With the chemical formula C15H10O6, the compound is characterized by its molecular weight of 290.24 g/mol. Its CAS number, 490-46-0, uniquely identifies it in chemical databases and literature, facilitating precise referencing in scientific discussions and industrial applications.

The (-)-Epicatechin enantiomer is particularly studied for its potent antioxidant properties, which are attributed to its ability to scavenge free radicals and inhibit oxidative stress. This property has made it a subject of extensive research in the fields of pharmacology, nutrition, and dermatology. The structural configuration of (-)-Epicatechin, with its stereocenter at the C-2 position, contributes to its unique interaction with biological targets, distinguishing it from its epimer (+)-epicatechin.

Recent advancements in metabolomics and systems biology have highlighted the role of (-)-Epicatechin in modulating cellular signaling pathways. Studies have demonstrated its ability to activate the AMP-activated protein kinase (AMPK) pathway, which is crucial for energy homeostasis and metabolic regulation. This mechanism has been linked to improved insulin sensitivity and reduced risk of type 2 diabetes, making (-)-Epicatechin a promising candidate for therapeutic intervention.

In addition to its metabolic effects, (-)-Epicatechin has shown significant potential in neuroprotection. Preclinical studies have indicated that it can cross the blood-brain barrier and exert protective effects against neurodegenerative diseases such as Alzheimer's and Parkinson's. The compound's ability to inhibit beta-amyloid aggregation and enhance acetylcholinesterase activity has been particularly noted in these investigations. These findings align with growing evidence supporting the cognitive benefits of flavonoids in aging populations.

The cardiovascular benefits of (-)-Epicatechin are another area of active research. Epidemiological studies have associated consumption of foods rich in flavonoids, such as cocoa and green tea, with reduced risk of cardiovascular diseases. Mechanistically, (-)-Epicatechin has been shown to improve endothelial function by upregulating nitric oxide synthase (NOS) expression and enhancing vasodilation. Furthermore, its anti-inflammatory properties contribute to reducing atherosclerosis progression by modulating lipid profiles and inhibiting pro-inflammatory cytokine production.

Anticancer properties have also been explored in relation to (-)-Epicatechin. Research suggests that it can induce apoptosis in various cancer cell lines by activating caspase-dependent pathways. Its ability to disrupt mitochondrial function and impair DNA replication further underscores its potential as an anticancer agent. While clinical trials are still ongoing, these preclinical findings have generated considerable interest in developing (-)-Epicatechin-based formulations for cancer therapy.

The role of (-)-Epicatechin in skin health is another emerging field of study. Topical application of this compound has been shown to protect against UV-induced oxidative damage by neutralizing reactive oxygen species (ROS). Moreover, its anti-inflammatory effects help in managing skin conditions such as eczema and psoriasis. These properties make (-)-Epicatechin a valuable ingredient in cosmetic formulations aimed at promoting skin vitality and preventing photodamage.

The bioavailability of (-)-Epicatechin remains a critical consideration in its therapeutic application. While dietary intake through natural sources like dark chocolate and red wine is common, bioavailability can be limited due to rapid metabolism by gut microbiota and conjugation with glucuronic acid. Recent research has focused on enhancing bioavailability through novel delivery systems such as nanoencapsulation or prodrugs. These innovations aim to ensure higher plasma levels of (-)-Epicatechin, thereby maximizing its biological effects.

In conclusion, (-)-Epicatechin (CAS No. 490-46-0) represents a multifaceted compound with extensive therapeutic potential across multiple disease domains. Its antioxidant, anti-inflammatory, metabolic regulatory, neuroprotective, cardiovascular protective, anticancer, and dermatological benefits underscore its significance as a natural product with broad applications in healthcare. Continued research efforts are expected to further elucidate its mechanisms of action and optimize delivery strategies for clinical translation.

490-46-0 ((-)-Epicatechin) Related Products

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Tiancheng Chemical (Jiangsu) Co., Ltd
(CAS:490-46-0)L-Epicatechin
LE10002;LE6541;LE2456283
Purity:99%/99%/99%
Quantity:25KG,200KG,1000KG/25KG,200KG,1000KG/25KG,200KG,1000KG
Price ($):Inquiry/Inquiry/Inquiry
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Amadis Chemical Company Limited
(CAS:490-46-0)(-)-Epicatechin
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Email