ProcyanidinB2 - Moligand™, ≥90% , CAS No.29106-49-8

CAS: 29106-49-8 Cat. No.: P136147 Molecular Weight: 578.52 PubChem CID: 122738

GRADE & PURITY Moligand™, ≥90%

Synonyms

BDBM50553253 | P17914 | AKOS008901339 | Proanthocyanidin B2 | PROCYANIDIN B2, (+)- | (2R,2'R,3R,3'R,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-2H,2'H-4,8'-bichromene-3,3',5,5',7,7'-hexol | (4,8'-BI-2H-1-BENZOPYRAN)-3,3',5,5',7,7'-HEXOL, 2,2'-B

Storage

Store at 2-8°C,Argon charged

Shipped In

Wet ice

Overview

Procyanidin B2 exerts a potent and beneficial role in reducing granulosa cell apoptosis and inducing autophagy process,and exerts a variety of potent protective pharmacological effects on diabetic complications.

Specifications

Synonyms

BDBM50553253 | P17914 | AKOS008901339 | Proanthocyanidin B2 | PROCYANIDIN B2, (+)- | (2R, 2'R, 3R, 3'R, 4R)-2, 2'-bis(3, 4-dihydroxyphenyl)-3, 3', 4, 4'-tetrahydro-2H, 2'H-4, 8'-bichromene-3, 3', 5, 5', 7, 7'-hexol | (4, 8'-BI-2H-1-BENZOPYRAN)-3, 3', 5, 5', 7, 7'-HEXOL, 2, 2'-B

Specifications & Purity

Moligand™, ≥90%

Biochemical and Physiological Mechanisms

Procyanidin B2 exerts a potent and beneficial role in reducing granulosa cell apoptosis and inducing autophagy process, and exerts a variety of potent protective pharmacological effects on diabetic complications. In vitro: Procyanidin B2 treatment decrease

Storage

Store at 2-8°C, Argon charged

Shipped In

Wet ice

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

Grade

Moligand™

Purity

≥90%

Names and Identifiers

• Pubchem Sid: 504756878
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756878
• 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,3R)-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-NFJBMHMQSA-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-/m1/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: 122738
• 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)

F2 Tclin Thrombin (11687 Activities)

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APP Tclin Amyloid-beta A4 protein (8510 Activities)

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HCT-8 (3484 Activities)

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MT4 (17854 Activities)

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TE-671 (161 Activities)

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A549 (127892 Activities)

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KB (17409 Activities)

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PBMC (10003 Activities)

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LPO Tbio Lactoperoxidase (15 Activities)

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SNCA Tchem Alpha-synuclein (10960 Activities)

Discover Target: SNCA

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Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

Discover Target: pol

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Hdac6 Histone deacetylase 6 (222 Activities)

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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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Streptococcus pyogenes (16140 Activities)

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Mycolicibacterium fortuitum (1335 Activities)

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Candida albicans (78123 Activities)

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Human immunodeficiency virus 1 (70413 Activities)

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Human immunodeficiency virus (3636 Activities)

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Trpa1 Transient receptor potential cation channel subfamily A member 1 (1003 Activities)

Discover Target: Trpa1

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Potato virus X (11 Activities)

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Simplexvirus (54 Activities)

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Liver microsome (341 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Refractive Index: 1.8
• Boil Point(°C): 955.32° C
• Melt Point(°C): 197-198°C
• 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. Su Xuexia, Bai Cuihua, Wang Xianghe, Liu Huilin, Zhu Yongcong, Wei Leping, Cui Zixiao, Yao Lixian.  (2022)  Potassium Sulfate Spray Promotes Fruit Color Preference via Regulation of Pigment Profile in Litchi Pericarp.  Frontiers in Plant Science,      [PMID:35774808] [10.3389/fpls.2022.925609]

4. Yuting Fan, Qingyu He, Chao Gan, Zhen Wen, Jiang Yi.  (2022)  Investigation of binding interaction between bovine α-lactalbumin and procyanidin B2 by spectroscopic methods and molecular docking.  FOOD CHEMISTRY,      [PMID:35217463] [10.1016/j.foodchem.2022.132509]

5. Zhang Haipin, Song Huijia, Tian Xuemeng, Wang Yue, Hao Yi, Wang Wenting, Gao Ruixia, Yang Wan, Ke YuShen, Tang Yuhai.  (2021)  Magnetic imprinted nanoparticles with synergistic tailoring of covalent and non-covalent interactions for purification and detection of procyanidin B2.  MICROCHIMICA ACTA,  188  (1): (1-12).  [PMID:33403455] [10.1007/s00604-020-04693-x]

6. Taotao Dai, Jun Chen, David Julian McClements, Ti Li, Chengmei Liu.  (2019)  Investigation the interaction between procyanidin dimer and α-glucosidase: Spectroscopic analyses and molecular docking simulation.  INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES,      [PMID:30794902] [10.1016/j.ijbiomac.2019.02.105]

7. Qian Li, Chengmei Liu, Ti Li, David Julian McClements, Yinxin Fu, Jiyan Liu.  (2018)  Comparison of phytochemical profiles and antiproliferative activities of different proanthocyanidins fractions from Choerospondias axillaris fruit peels.  FOOD RESEARCH INTERNATIONAL,      [PMID:30195524] [10.1016/j.foodres.2018.07.006]

8. Jie Zheng, Yu-yan An, Xin-xin Feng, Liang-ju Wang.  (2017)  Rhizospheric application with 5-aminolevulinic acid improves coloration and quality in ‘Fuji’ apples.  SCIENTIA HORTICULTURAE,      [PMID:] [10.1016/j.scienta.2017.06.004]

9. Yi-Long Ma, Zi-Tong Wang, Dong-Mei Yang, Zhi Li, Qian-Lan Wu, Xin Guo, Ya-Fang Shang, Kiran Thakur, Zhao-Jun Wei.  (2024)  Effect of processing and simulated digestion on phenolics, antioxidant and hypoglycemic potential of winter jujube.  LWT-FOOD SCIENCE AND TECHNOLOGY,      [PMID:] [10.1016/j.lwt.2024.116944]

10. Jin Peng, Xu Huiting, Guo Yongjun, Liu Silin, Bai Cuihua, Cao Laixin, Yao Lixian.  (2025)  The Sprays of Nanoparticles of Zinc Oxide and Titanium Dioxide Enhance Fruit Coloration in Litchi.  JOURNAL OF PLANT GROWTH REGULATION,      [PMID:] [10.1007/s00344-025-11792-7]

11. Yu Chang, Bowei Zhang, Yuze Jia, Xiaolu Shi, Yingshuang Lu, Fan Wei, Yunhui Zhang, Huan Lv, Lu Dong, Yan Zhang, Xiangwei Tang, Shuo Wang.  (2025)  Effects of dietary polyphenols addition and oxygen concentration on digestion and absorption of fat in roast beef patties.  FOOD CHEMISTRY,      [PMID:40222130] [10.1016/j.foodchem.2025.144280]

12. Mengru Li, Wei Zhang, Yuan Huang, Xiaoying Zhang, Wuernisha Kadeer, Leihong Mao, Yuqian Jiang, Rong Tsao, Yao Tang.  (2025)  Unravelling the migration of bioactive and volatile compounds coupled with water sublimation from grapes to recovered water during dynamic freeze-drying.  FOOD CHEMISTRY,      [PMID:41075660] [10.1016/j.foodchem.2025.146536]

13. Jingjing Liu, Yan Zhang, Hongwei Yu, Weijia Li, Longfei Li, Yizhou Chen, Shikun Liu, Lixin Qiao, Jiale Kuang, Zetao Chen, Shuang Li, Qingjun Liu.  (2026)  In-vitro tongue-inspired hydrogel sensor for wine astringency evaluation.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2026.117425]

14. Xueqiang Deng, Zhiqiang Li, Xuan Yi, Dong Ruan, Xiang Chen, Jun Luo.  (2026)  Calcium-Polyphenol Functionalized Black Phosphorus Nanosheet System for Osteoporosis Therapy via Macrophage Reprogramming and Bone Microenvironment Remodeling.  Advanced Healthcare Materials,      [PMID:] [10.1002/adhm.202504217]

15. Wenli Tang, Daiwen Zhu, Qilong Zeng, Huan Zhong.  (2026)  Rice Cultivation Reshapes Mercury Accumulation in Soil-Plant Systems.  ENVIRONMENTAL SCIENCE & TECHNOLOGY,      [PMID:] [10.1021/acs.est.5c16234]

16. Danfei Liu, Yuyang Chen, Xiaoxuan Li, Wenxuan Zhou, Changfan Zhang.  (2026)  Multifunctional Indicator Films of Polyvinyl Alcohol/Guar Gum (Anthocyanins and Houttuynia Essential Oil Pickering Emulsion) Aided by Residual Networks for Monitoring Pork Freshness.  Journal of Future Foods,      [PMID:] [10.1016/j.jfutfo.2026.03.018]