Bergenin - analytical standard, ≥98% , CAS No.477-90-7

CAS: 477-90-7 Cat. No.: B111464 Molecular Weight: 328.28 EC Number: 803-760-9

GRADE & PURITY Analytical standard, ≥98%

Synonyms

B4349 | EN300-19651064 | YWJXCIXBAKGUKZ-HJJNZUOJSA-N | A827340 | (2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydropyrano[3,2-c]isochromen-6(2H)-one | CCG-208553 | Pyrano[3,2-c][2]benzopyran-6(2H)-one,3,4,4a,10b-te

Storage

Store at 2-8°C

Shipped In

Wet ice

Specifications

Synonyms

B4349 | EN300-19651064 | YWJXCIXBAKGUKZ-HJJNZUOJSA-N | A827340 | (2R, 3S, 4S, 4aR, 10bS)-3, 4, 8, 10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3, 4, 4a, 10b-tetrahydropyrano[3, 2-c]isochromen-6(2H)-one | CCG-208553 | Pyrano[3, 2-c][2]benzopyran-6(2H)-one, 3, 4, 4a, 10b-te

Specifications & Purity

analytical standard, ≥98%

Storage

Store at 2-8°C

Shipped In

Wet ice

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

Grade

Analytical standard

Purity

≥98%

Names and Identifiers

• Canonical Smiles: COC1=C(C=C2C(=C1O)C3C(C(C(C(O3)CO)O)O)OC2=O)O
• IUPAC Name: (2R,3S,4S,4aR,10bS)-3,4,8,10-tetrahydroxy-2-(hydroxymethyl)-9-methoxy-3,4,4a,10b-tetrahydro-2H-pyrano[3,2-c]isochromen-6-one
• InChIKey: YWJXCIXBAKGUKZ-HJJNZUOJSA-N
• INCHI: 1S/C14H16O9/c1-21-11-5(16)2-4-7(9(11)18)12-13(23-14(4)20)10(19)8(17)6(3-15)22-12/h2,6,8,10,12-13,15-19H,3H2,1H3/t6-,8-,10+,12+,13-/m1/s1
• Isomeric SMILES: COC1=C(C=C2C(=C1O)[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)OC2=O)O
• Molecular Weight: 328.28
• Reaxy-Rn: 1354737
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1354737&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives
        • Level5 Hydroxybenzoic acid derivatives
          • Level6 Gallic acid and derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Hydroxybenzoic acid derivatives
• Direct Parent: Gallic acid and derivatives
• Alternative Parents: 2-benzopyrans Anisoles 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids Alkyl aryl ethers Oxanes Monosaccharides Secondary alcohols Carboxylic acid esters Lactones Dialkyl ethers Oxacyclic compounds Polyols Monocarboxylic acids and derivatives Primary alcohols Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Gallic acid or derivatives - Benzopyran - Isochromane - 2-benzopyran - Anisole - 1-hydroxy-4-unsubstituted benzenoid - 1-hydroxy-2-unsubstituted benzenoid - Alkyl aryl ether - Monosaccharide - Oxane - Secondary alcohol - Carboxylic acid ester - Lactone - Polyol - Oxacycle - Carboxylic acid derivative - Dialkyl ether - Ether - Organoheterocyclic compound - Monocarboxylic acid or derivatives - Organic oxygen compound - Hydrocarbon derivative - Primary alcohol - Organooxygen compound - Organic oxide - Alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as gallic acid and derivatives. These are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.
• External Descriptors: trihydroxybenzoic acid

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)

IL6 Tclin Interleukin-6 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TYR Tclin Tyrosinase (717 Activities)

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ACHE Tclin Acetylcholinesterase (18204 Activities)

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XDH Tclin Xanthine dehydrogenase (1038 Activities)

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TNF Tclin TNF-alpha (1897 Activities)

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ALB Tchem Serum albumin (2651 Activities)

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BGC-823 (3035 Activities)

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C8166 (1658 Activities)

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MCF7 (126967 Activities)

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PC-3 (62116 Activities)

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SGC-7901 (2773 Activities)

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THP-1 (11052 Activities)

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A549 (127892 Activities)

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HepG2 (196354 Activities)

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GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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IL6 Tclin Interleukin-6 (43 Activities)

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IKBKB Tchem Inhibitor of NF-kappa-B kinase (IKK) (78 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Escherichia coli (133304 Activities)

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Bacillus subtilis (32866 Activities)

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Plasmodium falciparum (966862 Activities)

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Mus musculus (284745 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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RAW264.7 (28094 Activities)

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J774.2 (197 Activities)

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NIH3T3 (5395 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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BCHE Cholinesterase (8742 Activities)

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Plasma (328 Activities)

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Chikungunya virus (1339 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: heat sensitive
• Melt Point(°C): 238°C
• Molecular Weight: 328.270 g/mol
• XLogP3: -1.000
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 328.079 Da
• Monoisotopic Mass: 328.079 Da
• Topological Polar Surface Area: 146.000 Ų
• Heavy Atom Count: 23
• Formal Charge: 0
• Complexity: 458.000
• 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. Huang Dan, Sun Chaoqun, Chen Min, Bai Shuyou, Zhao Xuanna, Wang Weiming, Geng Kang, Huang Wenbo, Zhao Tingting, Wu Bin, Zhang Guilin, Wu Dong, Xu Youhua.  (2022)  Bergenin ameliorates airway inflammation and remodeling in asthma by activating SIRT1 in macrophages to regulate the NF-κB pathway.  Frontiers in Pharmacology,      [PMID:36313381] [10.3389/fphar.2022.994878]

2. Min Chen, Cuifen Chen, Yun Gao, Dongming Li, Dan Huang, Ziyu Chen, Xuanna Zhao, Qiu Huang, Dong Wu, Tianwen Lai, Guomei Su, Bin Wu, Beixian Zhou.  (2020)  Bergenin-activated SIRT1 inhibits TNF-α-induced proinflammatory response by blocking the NF-κB signaling pathway.  PULMONARY PHARMACOLOGY & THERAPEUTICS,      [PMID:32615160] [10.1016/j.pupt.2020.101921]

3. Yinggui Zhu, Lili Zou, Qin Dong, Derong Jiang.  (2015)  Determination of bergenin based on the electrochemiluminescence quenching of tris(2,2′-bipyridine)-ruthenium(II).  LUMINESCENCE,  30  (8): (1269-1273).  [PMID:25808319] [10.1002/bio.2891]

4. Yanrong Zhu, Lichen Yao, Yilei Guo, Jing Zhang, Yufeng Xia, Zhifeng Wei, Yue Dai.  (2024)  Bergenin attenuates triptolide-caused premature ovarian failure in mice based on the antioxidant activity.  REPRODUCTIVE TOXICOLOGY,      [PMID:38735593] [10.1016/j.reprotox.2024.108608]

5. Yu-Zhen Zhang, Yi-Le Li, Zhi Jin, Mao-Fang He, Yi-Mei Tang, Jian Zhang, Bo Zhang.  (2024)  Fabrication of molecularly imprinted polymers based on magnetic covalent organic framework for highly selective and sensitive analysis of genistein in F. Philippinensis.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2024.110013]

6. Yao Sun, Shihao Cai, Hongting Liu, Conglu Zhao, Xiang Xu, Xiaoting Wang, Jia Zhang, Chaoyue Zheng, Keran Li, Shouchun Peng, Honggang Zhou, Aiguo Xu, Xiaoting Gu, Xiaoyu Ai, Cheng Yang.  (2025)  Bergenin and vitexin delivery platform using mouse lung fibroblasts-derived exosomes for bleomycin-induced pulmonary fibrosis therapy.  INTERNATIONAL JOURNAL OF PHARMACEUTICS,      [PMID:40456424] [10.1016/j.ijpharm.2025.125750]