20315-25-7
Procyanidin B1
CAS: 20315-25-7
Molecular Formula: C30H26O12
20315-25-7 - Names and Identifiers
20315-25-7 - Physico-chemical Properties
| Molecular Formula | C30H26O12 |
| Molar Mass | 578.528 |
| Density | 1.705±0.06 g/cm3(Predicted) |
| Melting Point | 231～232℃ |
| Boling Point | 955.3±65.0 °C(Predicted) |
| Specific Rotation(α) | +110.9 (c, 2 in Me2CO) |
| Solubility | Soluble in hot methanol, DMSO and other solvents, insoluble in petroleum ether. |
| Appearance | morphology neat |
| pKa | 9.29±0.60(Predicted) |
| Storage Condition | Inert atmosphere,2-8°C |
| MDL | MFCD01861512 |
| Physical and Chemical Properties | Chemical properties of light yellow powder, soluble in methanol, ethanol, DMSO and other organic solvents, derived from grape seeds. |
| Use | Use 1. Proanthocyanidin B1 is a type B proanthocyanidin, which exists in Ceylon cinnamon and has anti-inflammatory, antioxidant, anti-tumor and cardiovascular protective effects. 2, for content determination/identification/pharmacological experiments. Pharmacological effects: antioxidant activity, tumor inhibition. |
20315-25-7 - Risk and Safety
| Safety Description | 24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 3 |
| FLUKA BRAND F CODES | 10-23 |
| HS Code | 29329990 |
20315-25-7 - Upstream Downstream Industry
20315-25-7 - Reference
| Reference Show more | 1. Li Min, Guo Qing, Zhang Xiao. Simultaneous determination of six polyphenols in Fagopyrum dibotrys tablets by HPLC [J]. Journal of Pharmaceutical Analysis 2015(04):644-648. 2. Chen Xiaojing, He Jie, Yang Jianyun et al. Simultaneous determination of catechin gallate and epicatechin in grape seed extract by RP-HPLC method [J]. Journal of Pharmaceutical Analysis, 2015 035(004):723-727. 3. Yang daixiao, Chen Xiaojing, Hu Qiuju, etc. Determination of five polyphenols in grape seed extract by liquid chromatography-mass spectrometry [J]. Journal of Pharmaceutical Analysis, 2016(8):1330-1337. 4. Zhou Ting, Lei Runmei, Zhao Xiaodan, etc. Inhibitory effect of proanthocyanidins extracted from peanut red skin on acrylamide [J]. Modern food science and technology, 2016(10):66-71. 5. Mao Xue, Liu Yumei. Comparison of different analysis methods and content analysis of proanthocyanidins in grape branches [J]. Food Science, 2016, 37(12):169-175. 6. Ma You-chuan, Bi Jin-feng, Yi Jian-yong, Du Xi-Qian, Feng Shu-Han, Li Subin. Effect of pre-freezing on vacuum freeze-drying characteristics and quality of apple slices [J]. Journal of Agricultural Engineering, 2020,36(18):241-250. 7. Wang, Mengting, et al. "(Nelumbo nucifera Gaertn.) leaf against pancreatic α-amylase." International journal of biological macromolecules 120 (2018): 2589-2596.https://doi.org/10.1016/j.ijbiomac.20 8. Yang, Jing, et al. "Determination of active compounds in raspberry leaf extracts and the effects of extract intake on mice." Food Science and Technology 40 (2019): 124-131.https://doi.org/10.1590/fst.35518 9. Yang, Jing, et al." Determination of active compounds in raspberry leaf extracts and the effects of extract intake on mice." Food Science and Technology 40 (2019): 124-131.https://doi.org/10.1590/fst.35518 10. Yang, Jing, et al. "Comparisons of the active components in four unripe raspberry extracts and their activites." Food Science and Technology 39 (2019): 632-639.https://doi.org/10.1590/fst.27418 11. [IF=6.953] Mengting Wang et al."Inhibitory kinetics and mechanism of flavonoids from lotus (Nelumbo nucifera Gaertn.) leaf against pancreatic α-amylase."Int J Biol Macromol. 2018 Dec;120:2589 12. [IF=5.396] Jiachan Zhang et al."Understanding the role of extracts from sea buckthorn seed residues in anti-melanogenesis properties on B16F10 melanoma cells."Food Funct. 2018 Oct;9(10):5402-5416 13. [IF=5.279] Zhen-zhen Ge et al."Metabolites and Changes in Antioxidant Activity of A- Type and B- Type Proanthocyanidin Dimers after Incubation with Rat Intestinal Microbiota."J Agr Food Chem. 2015;63(41):8991-8998 14. [IF=7.514] Li Zhao et al."Synergistic inhibitory effects of procyanidin B2 and catechin on acrylamide in food matrix."Food Chem. 2019 Oct;296:94 15. [IF=7.514] Balarabe B. Ismail et al."High-intensity ultrasound processing of baobab fruit pulp: Effect on quality, bioactive compounds, and inhibitory potential on the activity of α-amylase and α-glucosidase."Food Chem. 2021 Nov;361:130144 16. [IF=6.513] Balarabe B. Ismail et al."Ultrasound-assisted adsorption/desorption for the enrichment and purification of flavonoids from baobab (Adansonia digitata) fruit pulp."Ultrason Sonochem. 2020 Jul;65:104980 17. [IF=4.952] Ting Zhao et al."The antioxidant property and α-amylase inhibition activity of young apple polyphenols are related with apple varieties."Lwt Food Sci Technol. 2019 Aug;111:252 18. [IF=4.952] Si Tan et al."The effects of drying methods on chemical profiles and antioxidant activities of two cultivars of Psidium guajava fruits."Lwt Food Sci Technol. 2020 Jan;118:108723 19. [IF=4.952] Yuxin Hao et al."Stability and mechanism of phenolic compounds from raspberry extract under in vitro gastrointestinal digestion."Lwt Food Sci Technol. 2021 Mar;139:110552 20. [IF=4.24] Nana Li et al."Characterization of phenolic compounds and anti-acetylcholinase activity of coconut shells."Food Biosci. 2021 Aug;42:101204 21. [IF=3.463] Jing Yang et al."Evaluation of physicochemical properties in three raspberries (Rubus idaeus) at five ripening stages in northern China."Sci Hortic-Amsterdam. 2020 Mar;263:109146 22. [IF=2.72] Meiling Han et al."Phenolic compounds present in fruit extracts of Malus spp. show antioxidative and pro-apoptotic effects on human gastric cancer cell lines."J Food Biochem. 2019 Nov;43(11):e13028 23. [IF=1.296] Han Meiling et al."Analysis of flavonoids and anthocyanin biosynthesis-related genes expression reveals the mechanism of petal color fading of Malus hupehensis (Rosaceae)."Braz J Bot. 2020 Mar;43(1):81-89 24. [IF=1.296] Shen Ting et al."Pigment profile and gene analysis revealed the reasons of petal color difference of crabapples."Braz J Bot. 2021 Jun;44(2):287-296 25. [IF=4.451] Suwen Liu et al."Castanea mollissima shell polyphenols regulate JAK2 and PPARγ expression to suppress inflammation and lipid accumulation by inhibiting M1 macrophages polarization."J Funct Foods. 2022 May;92:105046 26. [IF=7.514] YueTong Yu et al."Identification and Quantification of Oligomeric Proanthocyanidins, Alkaloids, and Flavonoids in Lotus Seeds: A Potentially Rich Source of Bioactive Compounds."Food Chem. 2022 Jan;:132124 27. [IF=7.514] Jie Meng et al."Conduction of a chemical structure-guided metabolic phenotype analysis method targeting phenylpropane pathway via LC-MS: Ginkgo biloba and soybean as examples."FOOD CHEMISTRY. 2022 Oct;390:133155 |
20315-25-7 - Uses and synthesis methods
biological activity
Procyanidin B1 is a polyphenol flavonoid substance, which exists in common fruits and can bind to TLR4/MD-2 complex and has anti-inflammatory activity.
in vitro study
Procyanidin B1 is a polyphenolic flavonoid isolated from fruits and fruit juices, binds to TLR4/MD-2 complex, and has anti-inflammatory activity. Procyanidin B1 causes cellular toxicity at concentrations >100 μg/mL. Procyanidin B1 (100 μg/mL) inhibits LPS-induced TNF-α production, and expression of MD-2, TRAF6, NF-κ B mRNA, phosphorylated p38 MAPK and NF-κ B protein in THP1 cells. Procyanidin B1 (50-100 µM) protects against Aβ oligomer-induced neuronal death. Procyanidin B1 potently inhibits the activation of caspase-3 at 100 µM, caspase-8 at concentrations of 30, 50, and 100 µM and caspase-9 at concentrations of 10, 30, 50, and 100 µM. Procyanidin B1 (10, 20, 30 μM) significantly and dose-dependently induces expression of ACO and CPT1, with no obvious effect on mRNA expression of PPARα.
Last Update：2024-04-10 22:29:15
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View History
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Raw Materials for 20315-25-7
[4,8'-Bi-2H-1-benzopyran]-3,3'-diol, 2,2'-bis[3,4-bis(phenylmethoxy)phenyl]-3,3',4,4'-tetrahydro-5,5',7,7'-tetrakis(phenylmethoxy)-, (2R,2'R,3R,3'S,4R)-
[4,8':4',8''-Ter-2H-1-benzopyran]-3,3',3'',5,5',5'',7,7',7''-nonol, 2,2',2''-tris(3,4-dihydroxyphenyl)-3,3',3'',4,4',4''-hexahydro-, (2R,2'R,2''R,3R,3'S,3''S,4R,4'R)-
Benzoic acid, 3,4,5-trihydroxy-, (2R,2'R,3R,3'S,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-3',5,5',7,7'-pentahydroxy[4,8'-bi-2H-1-benzopyran]-3-yl ester
5,7,3'',4''-Tetra-O-benzylepicatechin
PROCYANIDIN B7
[4,8':4',8''-Ter-2H-1-benzopyran]-3,3',3'',5,5',5'',7,7',7''-nonol, 2,2',2''-tris(3,4-dihydroxyphenyl)-3,3',3'',4,4',4''-hexahydro-, (2R,2'R,2''R,3R,3'S,3''S,4R,4'R)-
Benzoic acid, 3,4,5-trihydroxy-, (2R,2'R,3R,3'S,4R)-2,2'-bis(3,4-dihydroxyphenyl)-3,3',4,4'-tetrahydro-3',5,5',7,7'-pentahydroxy[4,8'-bi-2H-1-benzopyran]-3-yl ester
5,7,3'',4''-Tetra-O-benzylepicatechin
PROCYANIDIN B7