Procyanidin B1 - ≥98% , CAS No.20315-25-7

CAS: 20315-25-7 Cat. No.: P664537 Molecular Weight: 578.52 EC Number: 877-155-3 PubChem CID: 11250133

GRADE & PURITY ≥98%

Synonyms

(-)-Epicatechin (4β-8)-(+)-catechin | cis,trans′′-4,8′′-Bi-(3,3′,4′,5,7-Pentahydroxyflavane)

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Procyanidin B1, isolated from commonly eaten fruits, binds to the TLR4/MD-2 complex and has anti-inflammatory activity.
Proanthocyanidin B1 is a phenolic compound found in fruits. It is widely used as an indicator for the adulteration of fruit juices. It has strong antioxidant properties

Specifications

Synonyms

(-)-Epicatechin (4β-8)-(+)-catechin | cis, trans′′-4, 8′′-Bi-(3, 3′, 4′, 5, 7-Pentahydroxyflavane)

Specifications & Purity

≥98%

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: C1C(C(OC2=C1C(=CC(=C2C3C(C(OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• IUPAC Name: (2R,3S)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-4-yl]-3,4-dihydro-2H-chromene-3,5,7-triol
• InChIKey: XFZJEEAOWLFHDH-UKWJTHFESA-N
• INCHI: 1S/C30H26O12/c31-13-7-20(37)24-23(8-13)41-29(12-2-4-16(33)19(36)6-12)27(40)26(24)25-21(38)10-17(34)14-9-22(39)28(42-30(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,22,26-29,31-40H,9H2/t22-,26+,27+,28+,29+/m0/s1
• Isomeric SMILES: C1[C@@H]([C@H](OC2=C1C(=CC(=C2[C@@H]3[C@H]([C@H](OC4=CC(=CC(=C34)O)O)C5=CC(=C(C=C5)O)O)O)O)O)C6=CC(=C(C=C6)O)O)O
• PubChem CID: 11250133
• Molecular Weight: 578.52

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Flavonoids
      • Subclass Biflavonoids and polyflavonoids

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Flavonoids
• Subclass: Biflavonoids and polyflavonoids
• Intermediate Tree Nodes: Not available
• Direct Parent: Biflavonoids and polyflavonoids
• Alternative Parents: B-type proanthocyanidins Catechins 3'-hydroxyflavonoids 3-hydroxyflavonoids 4'-hydroxyflavonoids 5-hydroxyflavonoids 7-hydroxyflavonoids 1-benzopyrans Catechols 1-hydroxy-4-unsubstituted benzenoids 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Benzene and substituted derivatives Secondary alcohols Oxacyclic compounds Polyols Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: B-type proanthocyanidin - Bi- and polyflavonoid skeleton - Proanthocyanidin - Catechin - Flavan-3-ol - Hydroxyflavonoid - 3'-hydroxyflavonoid - 7-hydroxyflavonoid - 5-hydroxyflavonoid - 4'-hydroxyflavonoid - 3-hydroxyflavonoid - Flavan - Chromane - 1-benzopyran - Benzopyran - Catechol - Phenol - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - 1-hydroxy-4-unsubstituted benzenoid - Benzenoid - Monocyclic benzene moiety - Secondary alcohol - Polyol - Organoheterocyclic compound - Oxacycle - Ether - Hydrocarbon derivative - Alcohol - Organic oxygen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.
• External Descriptors: Proanthocyanidins

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

MT4 (17854 Activities)

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SNCA Tchem Alpha-synuclein (10960 Activities)

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Associated Targets(non-human)

Salmonella paratyphi (588 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Enterobacter cloacae (7976 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Mycolicibacterium fortuitum (1335 Activities)

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Candida albicans (78123 Activities)

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Human immunodeficiency virus (3636 Activities)

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HT-22 (3261 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Air Sensitive； light sensitive
• Molecular Weight: 578.500 g/mol
• XLogP3: 2.400
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 3
• Exact Mass: 578.142 Da
• Monoisotopic Mass: 578.142 Da
• Topological Polar Surface Area: 221.000 Ų
• Heavy Atom Count: 42
• Formal Charge: 0
• Complexity: 925.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Lei He, Qian Hu, Jiukai Zhang, Ranran Xing, Yongsheng Zhao, Ning Yu, Ying Chen.  (2023)  An integrated untargeted metabolomic approach reveals the quality characteristics of black soybeans from different geographical origins in China.  FOOD RESEARCH INTERNATIONAL,      [PMID:37254343] [10.1016/j.foodres.2023.112908]

2. Lei He, Qian Hu, Liyang Wei, Xuliyang Ge, Ning Yu, Ying Chen.  (2023)  Unravelling dynamic changes in non-volatile and volatile metabolites of pulses during soaking: An integrated metabolomics approach.  FOOD CHEMISTRY,      [PMID:37141754] [10.1016/j.foodchem.2023.136231]

3. Ming-Jun Tan, Ying Li, Si-Qi Zhao, Fu-Hao Yue, Die-Jia Cai, Jin-Tao Wu, Xin-An Zeng, Jian Li, Zhong Han.  (2024)  Synergistic ultrasound pulsed electric field extraction of litchi peel polyphenols and determination of their properties.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:38246440] [10.1016/j.ijbiomac.2024.129613]

4. Qi-Yuan Feng, Jiang-Tao Zhong, Hai-Ming Sun, Zheng Luo, Yu-Chen Jiang, Jian Song.  (2025)  Dietary procyanidin B1 attenuates fibrogenesis and inflammation in hepatic fibrosis: research on the possible health benefits of procyanidin B1.  Food & Function,      [PMID:40493038] [10.1039/D5FO01415H]

5. Yang Liu, Jingzhong Zheng, Xin Zheng, Dan Zhou, Hang Ma, Xue Zhou, Fahuan Ge.  (2025)  A Proanthocyanidins-Rich Cili (Rosa roxburghii) Fruit Extract Protects CCl4-Induced Mouse Hepatic Fibrosis via Modulation of Ferroptosis and Gut Microbiota.  Nutrients,  17  (21): (3463).  [PMID:41228535] [10.3390/nu17213463]