CAS: 80651-76-9; (5Ar,10As)-2-((1S,2R,3S)-2-(2,4-Dihydroxybenzoyl)-2',4'-Dihydroxy-5-Methyl-1,2,3,6-Tetrahydro-[1,1'-Biphenyl]-3-yl)-1,3,8,10A-Tetrahydroxy-5A-(3-Methylbut-2-En-1-yl)-5A,10A-Dihydro-11H-Benzofuro[3,2-B]Chromen-11-One

该化合物是一种天然化合物,主要来源于植物物种* Morus alba* 的根部,通称为白,该化合物属于氟芳素类,其特点是复杂的多酚结构,有助于生物活动.Sanggenon C具有各种药理特性,包括抗氧化剂,抗炎和潜在的抗癌影响,因此对医药化学和自然产品研究感兴趣.其行动机制可能涉及信号路径的调节和特定酶的抑制.此外,Sanggenon C的溶性性和稳定性可能因溶剂和环境条件而不同,而这些条件是其在治疗环境中应用的重要因素.随着研究的继续进行,正在探讨其生物活动的各个方面和对健康和医学的潜在应用,强调天然化合物在药物发现和开发中的重要性.

英文名称(5Ar,10As)-2-((1S,2R,3S)-2-(2,4-Dihydroxybenzoyl)-2',4'-Dihydroxy-5-Methyl-1,2,3,6-Tetrahydro-[1,1'-Biphenyl]-3-yl)-1,3,8,10A-Tetrahydroxy-5A-(3-Methylbut-2-En-1-yl)-5A,10A-Dihydro-11H-Benzofuro[3,2-B]Chromen-11-One
中文名称桑根酮C
IUPAC名称2-((1S,2R,3S)-2-(2,4-dihydroxybenzoyl)-2',4'-dihydroxy-5-methyl-1,2,3,6-tetrahydro-[1,1'-biphenyl]-3-yl)-1,3,8,10a-tetrahydroxy-5a-(3-methylbut-2-en-1-yl)-5a,10a-dihydro-11H-benzofuro[3,2-b]chromen-11-one
其它别名Sanggenone; Sanggenon C; (5Ar,10As)-2-[6β-(2,4-Dihydroxybenzoyl)-5α-(2,4-Dihydroxyphenyl)-3-Methyl-2-Cyclohexene-1β-Yl]-5A,10A-Dihydro-1,3,8,10A-Tetrahydroxy-5A-(3-Methyl-2-Butenyl)-11H-Benzofuro[3,2-B][1]Benzopyran-11-One; 2-[(1S)-6β-(2,4-Dihydroxybenzoyl)-5α-(2,4-Dihydroxyphenyl)-3-Methyl-2-Cyclohexene-1β-Yl]-5A,10A-Dihydro-1,3,8,10Aβ-Tetrahydroxy-5Aβ-(3-Methyl-2-Butenyl)-11H-Benzofuro[3,2-B][1]Benzopyran-11-One; Sanggenone C; (5Ar,10As)-2-[(1S,5S,6R)-6-(2,4-Dihydroxybenzoyl)-5-(2,4-Dihydroxyphenyl)-3-Methyl-2-Cyclohexen-1-Yl]-5A,10A-Dihydro-1,3,8,10A-Tetrahydroxy-5A-(3-Methyl-2-Buten-1-yl)-11H-Benzofuro[3,2-B][1]Benzopyran-11-One; 11H-Benzofuro[3,2-B][1]Benzopyran-11-One, 2-[(1S,5S,6R)-6-(2,4-Dihydroxybenzoyl)-5-(2,4-Dihydroxyphenyl)-3-Methyl-2-Cyclohexen-1-Yl]-5A,10A-Dihydro-1,3,8,10A-Tetrahydroxy-5A-(3-Methyl-2-Buten-1-yl)-, (5Ar,10As)-; (5Ar,10As)-2-((1S,2R,3S)-2-(2,4-Dihydroxybenzoyl)-2',4'-Dihydroxy-5-Methyl-1,2,3,6-Tetrahydro-[1,1'-Biphenyl]-3-yl)-1,3,8,10A-Tetrahydroxy-5A-(3-Methylbut-2-En-1-yl)-5A,10A-Dihydro-11H-Benzofuro[3,2-B]Chromen-11-One
CAS编号80651-76-9
MFCD编号:MFCD32004761
分子式:C40H36O12分子量:708.72
产品CID: 1801548
产品分类生物化工 → 提取物

相似结构搜索
产品信息参考;;
InChIKey: XETHJOZXBVWLLM-XKZYWWHCNA-N
XETHJOZXBVWLLM-HUKCQOFTSA-N
计算化学: 氢键受体数12.0氢键供体数8.0可旋转键数6.0

物理性质

熔点> 240°C (分解)
沸点999.3±65.0 °C at 760 mmHg
闪点312.7±27.8 °C
密度1.5±0.1 g/cm3
pKa:6.61±0.60(预测)
PSA:214.44
LogP:7.94
折射率1.727
蒸汽压0.0±0.3 mmHg at 25°C
溶解性Acetone (Slightly), Methanol (Slightly)
外观形态黄色固体
储存条件防潮, -20°C 冰箱, 在惰性气其中
产品应用该化合物是一种天然的先发制人叶片,抑制了肿瘤细胞蛋白质活性和细胞活性.

MSDS等安全信息

合成工艺路线路线简述

📜[4-[3-(2,4-Diacetyloxyphenyl)Prop-2-Enoyl]-3-Hydroxyphenyl] Acetate,(3R,11R)-7,11,20-Tris[[tert-Butyl(Dimethyl)Silyl]Oxy]-16,16-Dimethyl-3-(3-Methylbut-2-Enyl)-2,10,15-Trioxapentacyclo[11.8.0.03,11.04,9.014,19]Henicosa-1(21),4(9),5,7,13,17,19-Heptaen-12-One置于三苯基硼酸酯,(S)-3,3'-二溴-1,1'-联-2-萘酚体系中,化学反应 50.0H,以98%的收率获得产物
参考文献:黄酮类 Diels-Alder 天然产物 Sanggenons C 和 O 的不对称合成
标题:黄酮类 Diels-Alder 天然产物 Sanggenons C 和 O 的不对称合成
摘要:金属催化的双烯丙氧基黄酮双克莱森重排已被用于合成天然产物桑格农 A 和桑格酚 F 的氢苯并呋喃 [3,2-B] 色烯酮核心结构.此外,催化,对映选择性 [2'-羟基查尔酮的 4+2] 环加成已使用 B(Oph)3/binol 复合物完成.黄酮类 Diels-Alder 天然产物 Sanggenons C 和 O 的不对称合成已通过涉及 [4+2] 环加成的外消旋混合物(立体发散 Rrm)的立体发散反应实现.
DOI:10.1021/jacs.5B12778

海关参考信息

2901210000-乙烯
2901220000-丙烯
2902600000-乙苯
2902700000-异丙基苯
💡 提示：海关信息按照顺序优先匹配，如需确认的海关信息，请参考相关资料。
详情请参考：📖 海关编码查询和海关进出口税则

专利信息

专利号:US-2007232495-A1
优先权日:2006-03-24
标题:Compositions and methods to add value to plant products, increasing the commercial quality, resistance to external factors and polyphenol content thereof
发明人：NAPPA ALVARO O; LORENZINI FELIPE C; SANHUEZA ANDRES L
权利人:NAPPA ALVARO O; LORENZINI FELIPE C; SANHUEZA ANDRES L
摘要:The invention is related to compositions and methods that naturally protect plant tissues against ultraviolet radiation and temperature, thus giving protection against sunburn to plants, plant parts, fruits and/or flowers during their development. The invention is also related to compositions and methods to naturally improve the color of plants, plant parts, fruits and/or flowers by inducing the natural synthesis of flavonoids and anthocyanins present in plants. Likewise, the present invention is directed to improving the nutritional value of plants, plant parts, fruits and/or flowers by increasing the normal levels of polyphenolic compounds, especially flavonoids, present therein. Additionally, the present invention is related to compositions and methods that give more resistance to plants, plant parts, fruits and/or flowers against pathogens as bacteria and fungi. Finally, the present invention is related to plants, plant parts, fruits, flowers and/or propagating material treated with the compositions described in the present document.

其他信息查阅

供应商参考报价(招募中)

品牌试剂参考报价(招募中)

实用工具

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主要参考文献

1: Huang H, Liu N, Zhao K, Zhu C, Lu X, Li S, Lian W, Zhou P, Dong X, Zhao C, Guo H, Zhang C, Yang C, Wen G, Lu L, Li X, Guan L, Liu C, Wang X, Dou QP, Liu J. Sanggenon C decreases tumor cell viability associated with proteasome inhibition. Front Biosci (Elite Ed). 2011 Jun 1;3:1315-25.
2: Dat NT, Binh PT, Quynh le TP, Huong HT, Minh CV. Sanggenon C and O inhibit NO production, iNOS expression and NF-κB activation in LPS-induced RAW264.7 cells. Immunopharmacol Immunotoxicol. 2012 Feb;34(1):84-8. doi: 10.3109/08923973.2011.580755. Epub 2011 May 26. doi: 10.1021/jacs.5b12778. Epub 2016 Jan 19.
4: Baburajeev CP, Dhananjaya Mohan C, Ananda H, Rangappa S, Fuchs JE, Jagadish S, Sivaraman Siveen K, Chinnathambi A, Ali Alharbi S, Zayed ME, Zhang J, Li F, Sethi G, Girish KS, Bender A, Basappa, Rangappa KS. Development of Novel Triazolo-Thiadiazoles from Heterogeneous "Green" Catalysis as Protein Tyrosine Phosphatase 1B Inhibitors. Sci Rep. 2015 Sep 21;5:14195. doi: 10.1038/srep14195.

合成参考文献

参考文献:10.3109/08923973.2011.580755
摘要:Dat NT, Xuan Binh PT, Phuong Quynh LT, Huong HT, Van Minh C. Sanggenon C and O inhibit NO production, iNOS expression and NF-κB activation in LPS-induced RAW264.7 cells. Immunopharmacology and Immunotoxicology. 2011 May 26;34(1):84–8. doi: 10.3109/08923973.2011.580755.