CAS: 29106-49-8; (2R,2'R,3R,3'R,4R)-2,2'-Bis(3,4-Dihydroxyphenyl)-[4,8'-Bichromane]-3,3',5,5',7,7'-Hexaol

该化合物是一种类氟化物,具体来说是一种丙烯菊酯,一种丙烯菊酯,一种丙烯菊酯和摇头丸的聚合物,通常存在于各种植物中,特别是水果,种子和树皮中,有助于某些食物的营养品味.Procyanidin B2以其抗氧化性特性而著称,它有助于消除自由基质,并可能促进各种健康惠益,包括心血管保护和防炎效应.该化合物呈现一种以多种氢氧基为特征的复杂结构,加强了其再活性和生物活动.它溶于有机溶剂中,在水中溶性有限.Procyanidin B2经常因其潜在的治疗用途,包括其在改善血管健康方面的作用及其对代谢性失调的影响而受到研究.此外,它对于食品工业具有作为自然防腐和口味强化剂的潜力,因此对它很感兴趣.

结构式图片

上下游产品

CAS号223387-28-8 5,7,3',4'-tetra... | CAS号442626-19-9 3',4',5,7-tetra... | CAS号87292-49-7 tetrabeuzyl-(-)... | CAS号20728-73-8 5,7,3',4'-四-O-苄基儿茶素 | CAS号87292-54-4 (2R)-2-[3,4-bis... | CAS号154-23-4 儿茶精; 儿茶素; (2R,3... | CAS号256236-25-6 (2R,3R)-2-[3,4-... | CAS号490-46-0 表儿茶素(EC) | CAS号79907-44-1 原花青素B2-3,3'-二-O... | CAS号490-46-0 表儿茶素(EC) | CAS号154-23-4 儿茶精; 儿茶素; (2R,3... | CAS号41743-41-3 原花青素A2

合成工艺路线路线简述

  • 合成目标产物 Procyanidin B2 主要起始原料 L-Epicatechin
  • (文献来源)合成步骤主要原料 L-Epicatechin
[(2R,3R,4R)-2-(3,4-二羟基苯基)-4-[(2R,3R)-2-(3,4-二羟基苯基)-5,7-二羟基-3-(3,4,5-三羟基苯甲酰基)氧基-色满-8-基]-5,7-二羟基-色满-3-基]3,4,5-三羟基苯甲酸酯置于单宁酶体系中,用 水 用作溶剂,化学反应 1.0H,反应生成原花青素 B2
参考文献:Stilbene Glycoside Gallates And Proanthocyanidins From Polygonum Multiflorum
标题:Stilbene Glycoside Gallates And Proanthocyanidins From Polygonum Multiflorum
摘要:Two New Stilbene Glycoside Gallates And Proanthocyanidins Were Isolated From P. Multiflorum. The Stilbenes Were 2"-And 3"-O-Monogalloyl Esters Of 2,3,5,4''-Tetrahydroxystilbene 2-O-.Beta.-D-Glucopyranoside.
Doi:10.1016/s0031-9422(00)95282-8

专利信息


专利号:US-9133176-B2
优先权日:2002-02-15
标题:Isolation, purification and synthesis of procyanidin B2 and uses thereof
发明人:CASTILLO GERARDO; NGUYEN BETH; CHOI PAULA; LARSEN LESLEY; LORIMER STEPHEN; SNOW ALAN
权利人:CASTILLO GERARDO; NGUYEN BETH; CHOI PAULA; LARSEN LESLEY; LORIMER STEPHEN; SNOW ALAN; PROTEOTECH INC
摘要:Methods for the synthesis, isolation, and purification of procyanidin B2 are disclosed. The synthetic methods utilize epicatechin as a starting material and produce procyanidin B2 in high yields. The isolation methods extract procyanidin B2 from a sample of bark powder from plant matter of the genus Uncaria . The isolated and/or synthesized procyanidin B2 is used to treat amyloid disease, such as Alzheimer's disease and Parkinson's disease as well as improve cognitive performance and increase learning and memory in Alzheimer's patients. Pharmaceutical compositions containing the synthesized and/or isolated procyanidin B2 are also disclosed.

专利号:US-7126014-B2
优先权日:2000-09-05
标题 :Synthesis of epecatechin-4α, 8-epicatechin and -catechin dimers and derivatives thereof
发明人:KOZIKOWSKI ALAN P; ROMANCZYK JR LEO J; TUECKMANTEL WERNER
权利人:MARS INC
摘要:Oligomeric procyanidins containing 4α-linked epicatechin units are rare in nature and have hitherto not been accessible through stereoselective synthesis. Provided herein is the preparation of the prototypical dimer, epicatechin-4α,8-epicatechin, by reaction of the protected 4-ketones with aryllithium reagents derived by halogen/metal exchange from the aryl bromides. Removal of the 4-hydroxyl group from the resulting tertiary benzylic alcohols is effected by tri-n-butyltin hydride and trifluoroacetic acid in a completely stereoselective manner, resulting in hydride delivery exclusively from the β face.

专利号:EP-1921076-A1
优先权日:2002-10-11
标题:systhesis of procyanidin B2
发明人:CASTILLO GERARDO M; NGUYEN BETH P; CHOI PAULA Y; LARSEN LESLEY; LORIMER STEPHEN D; SNOW ALAN D
权利人:PROTEOTECH INC
摘要:Methods for the synthesis of procyanidin B2 are disclosed. The synthetic methods utilize epicatechin as a starting material and produce procyanidin BZ in high yields.

专利号:US-2007036742-A1
优先权日:2005-08-09
标题 :Methods and compositions for modulating hair growth or regrowth
发明人:ROUFS JAMES B; DUVEL LANE A; FAST DAVID J; GLYNN KELLY M
权利人:ACCESS BUSINESS GROUP INT LLC
摘要:The present invention relates to compositions and methods for modulating hair growth or regrowth. The compositions of the present invention comprise extracts of one or more of the following: Boswellia serrata, Undaria pinnatifida, green tea (e.g., Camellia sinensis ), shiso, Pureraria mirifica, luteolin (e.g. Perilla ocymoides leaf extract), astilbin, vitamin E, amentoflavone, tetrahydropiperine, licochalcone, astaxanthin, red clover, Brassica juncea, unfermented green rooibos, enzyme CoQ10, salvia, ximenynic acid, hops oleoresin, apple, soy, saw palmetto, or ellagic extract, or any derivative thereof. In particular, the compositions and methods of the present invention can be used to stimulate or increase hair growth and/or prevent or slow the loss of hair by having one or more of the following functions: (a) inhibiting synthesis of DHT; (b) inhibiting proteasomal activity; (c) inhibiting IL-1 activity; (d) increasing vascularization; (e) increasing expression of vascular endothelial growth factor; (f) increasing expression of keratinocyte growth factor; (g) inhibiting inflammation; or (h) acting as an antibacterial.

专利号:US-2003100775-A1
优先权日:2000-09-05
标 题 :Synthesis of 4alpha-arylepicatechins

专利号:US-2007197804-A1
优先权日:2000-09-05
标题:Synthesis of 4alpha-arylepicatechins
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主要参考文献


1: Chen J, Zhong K, Jing Y, Liu S, Qin S, Peng F, Li D, Peng C. Procyanidin B2: A promising multi-functional food-derived pigment for human diseases. Food Chem. 2023 Sep 15;420:136101. doi: 10.1016/j.foodchem.2023.136101. Epub 2023 Apr 7. Erratum in: Food Chem. 2024 Feb 1;433:137359. 13(7):594. doi: 10.1038/s41419-022-05051-w.
3: Zou YP, Zhang QC, Zhang QY, Jiang LB, Li XL. Procyanidin B2 alleviates oxidative stress-induced nucleus pulposus cells apoptosis through upregulating Nrf2 via PI3K-Akt pathway. J Orthop Res. 2023 Jul;41(7):1555-1564. doi: 10.1002/jor.25492. Epub 2022 Dec 10.
177:106127. doi: 10.1016/j.phrs.2022.106127. Epub 2022 Feb 10. 14(9):1756. doi: 10.3390/nu14091756.

合成参考文献


参考文献:10.1021/np010414l
摘要:Lin L, Kuo Y, Chou C. Immunomodulatory Proanthocyanidins from Ecdysanthera utilis. J. Nat. Prod. 2002 Mar 14;65(4):505–8. doi: 10.1021/np010414l.
参考文献:10.1021/np030510h
摘要:Dumontet V, Hung NV, Adeline M, Riche C, Chiaroni A, Sévenet T, Guéritte F. Cytotoxic Flavonoids and α-Pyrones from Cryptocarya obovata. J. Nat. Prod. 2004 May 01;67(5):858–62. doi: 10.1021/np030510h.
参考文献:10.1007/s11356-021-15594-8
摘要:El Omari N, Bakha M, Imtara H, Guaouguaoua F, Balahbib A, Zengin G, Bouyahya A. Anticancer mechanisms of phytochemical compounds: focusing on epigenetic targets. Environmental Science and Pollution Research. 2021 Jul 26;28(35):47869–903. doi: 10.1007/s11356-021-15594-8.
参考文献:10.1007/s13197-021-05119-z
摘要:Acosta-Otálvaro E, Valencia-Gallego W, Mazo-Rivas JC, García-Viguera C. Cocoa extract with high content of flavan 3-ols, procyanidins and methylxanthines. Journal of Food Science and Technology. 2021 May 04;59(3):1152–61. doi: 10.1007/s13197-021-05119-z.
参考文献:10.1007/s13668-021-00388-8
摘要:Afsar B, Afsar RE, Ertuglu LA, Covic A, Kanbay M. Nutrition, Immunology, and Kidney: Looking Beyond the Horizons. Curr Nutr Rep. 2022 Mar;11(1):69–81. doi: 10.1007/s13668-021-00388-8.
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