CAS: 80225-53-2; (4Br,8As,9S,10S)-3,4,10-Trihydroxy-2-Isopropyl-8,8-Dimethyl-6,7,8,8A,9,10-Hexahydro-5H-9,4B-(Epoxymethano)Phenanthren-12-One

该化合物是天然化合物,主要来自迷迭香(罗斯马林斯外皮),被归类为单体动物,以其独特的芳香特性著称,有助于玫瑰香味的独特气味;Rosmanol展示了各种生物活动,包括抗氧化剂,抗微生物和抗炎效应,使其对食品保存和可能的治疗应用都感兴趣;该化合物通常见于基本油类,并研究其潜在的健康惠益,包括其在增强认知功能方面的作用及其对氧化性压力的防护作用;就物理特性而言,罗曼纽素一般不具有色性,对浅色黄色液体和香草芳香味无色;其溶性特征允许其用于各种配方,包括化妆品和香味.总体而言,玫瑰素因其功能特性不同,在烹饪和制药业都是一种有价值的化合物.

结构式图片

物理性质

MSDS等安全信息

上下游产品

CAS号5957-80-2 鼠尾草酚 | CAS号380429-82-3 carnosic acid q... | CAS号3650-09-7 鼠尾草酸

合成工艺路线路线简述

  • 合成目标产物 Rosmanol 主要起始原料 Carnosol
  • 5957-80-2 = 80225-53-2
    反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Acetone,Water; Rt
    标题:Inhibition Of Squalene Synthase Of Rat Liver By Abietane Diterpenes Derivatives
    作者:Macias-Alonso,Mariana; Et Al
    参考文献:Natural Product Research 日期:2021 卷标:35(17) 页码:2972-2976]

    5957-80-2 = 80225-53-2
    反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Acetone,Water
    标题:Semisynthesis Of Rosmanol And Its Derivatives. Easy Access To Abietatriene Diterpenes Isolated From The Genus Salvia With Biological Activities
    作者:Marrero,Joaquin G.; Et Al
    参考文献:Journal Of Natural Products 日期:2002 卷标:65(7) 页码:986-989]

    5957-80-2 = 80225-53-2
    反应条件:1.1 Reagents: Sodium Bicarbonate Solvents: Acetone,Water; 6.5 H,Rt
    标题:Biomimetic Syntheses Of C23 Terpenoids: Structural Revision Of Salyunnanin A And Confirmation Of Hassanane
    作者:Zhang,Xun; Et Al
    参考文献:Organic Chemistry Frontiers 日期:2018 卷标:5(23) 页码:3469-3475]

    3650-09-7 = 80225-53-2
    反应条件:1.1 Reagents: Hydrochloric Acid,Hydrogen Peroxide Catalysts: Iron Chloride (Fecl3) Solvents: Acetic Acid,Water; 15 °C; 4 H,15 °C2.1 Reagents: Sodium Bicarbonate Solvents: Acetone,Water; 6.5 H,Rt
    标题:Biomimetic Syntheses Of C23 Terpenoids: Structural Revision Of Salyunnanin A And Confirmation Of Hassanane
    作者:Zhang,Xun; Et Al
    参考文献:Organic Chemistry Frontiers 日期:2018 卷标:5(23) 页码:3469-3475
📜鼠尾草酸置于氧气,碳酸氢钠体系中,用 丙酮 作为反应溶剂,20.0 °C,10.0 Kpa 条件下,反应 10.5H,反应生成 迷迭香酚
参考文献:香豆酚及其衍生物的半合成.容易获得从鼠尾草属中分离出来的松香三萜二烯,具有生物活性.
标题:香豆酚及其衍生物的半合成.容易获得从鼠尾草属中分离出来的松香三萜二烯,具有生物活性.
摘要:已知的二萜rosmanol(3),Rosmaquinone(4),7-甲氧基rosmanol(5),7-Ethoxyrosmanol(6),Galdosol(7)和epirosmanol(8)是由鼠李糖酚(2),丹参物种中存在丰富的天然产物.这些半合成二萜的物理和光谱数据与真实的天然样品的数据相同,文献报道的数据也相同.这些松果二萜具有非常有趣的生物学活性,并以少量存在于丹参中.因此,本文所述的半合成方法代表了一种获得这些化合物的有效替代方法.此外,通过与ph3P / Nbs在ch2Cl2中反应,从16-羟基香茅醇(9)获得了已知的二萜16-羟基香豆酚(10)和新的芳族二萜11.
DOI:10.1021/np010565O

海关参考信息

专利信息


专利号:US-8257754-B2
优先权日:2002-10-21
标 题:Synergistic compositions that treat or inhibit pathological conditions associated with inflammatory response
发明人：TRIPP MATTHEW L; BABISH JOHN G; BLAND JEFFREY S; DARLAND GARY K; LERMAN ROBERT; LUKACZER DANIEL O; LISKA DEANN J; HOWELL TERRENCE M
权利人:TRIPP MATTHEW L; BABISH JOHN G; BLAND JEFFREY S; DARLAND GARY K; LERMAN ROBERT; LUKACZER DANIEL O; LISKA DEANN J; HOWELL TERRENCE M; METAPROTEOMICS LLC
摘要:A natural formulation of compounds that would to modulate inflammation is disclosed. The formulation would also inhibit expression of COX-2, inhibit synthesis of prostaglandins selectively in target cells, and inhibit inflammatory response selectively in target cells. The compositions containing at least one fraction isolated or derived from hops. Other embodiments relate to combinations of components, including at least one fraction isolated or derived from hops, tryptanthrin and conjugates thereof, rosemary, an extract or compound derived from rosemary, a triterpene species, or a diterpene lactone or derivatives or conjugates thereof.

专利号:US-8486457-B2
优先权日:2002-10-21
标 题:Compositions that treat or inhibit pathological conditions associated with inflammatory response
发明人：TRIPP MATTHEW L; BABISH JOHN G; BLAND JEFFREY S; DARLAND GARY; LERMAN ROBERT; LUKACZER DANIEL O; LISKA DEANN J; HOWELL TERRENCE
权利人:TRIPP MATTHEW L; BABISH JOHN G; BLAND JEFFREY S; DARLAND GARY; LERMAN ROBERT; LUKACZER DANIEL O; LISKA DEANN J; HOWELL TERRENCE; METAPROTEOMICS LLC
摘要:A natural formulation of compounds that would to modulate inflammation is disclosed. The formulation would also inhibit expression of COX-2, inhibit synthesis of prostaglandins selectively in target cells, and inhibit inflammatory response selectively in target cells. The compositions containing at least one fraction isolated or derived from hops. Other embodiments relate to combinations of components, including at least one fraction isolated or derived from hops, tryptanthrin and conjugates thereof, rosemary, an extract or compound derived from rosemary, a triterpene species, or a diterpene lactone or derivatives or conjugates thereof.

专利号:US-8557306-B2
优先权日:2001-06-20
标 题 :Compositions that treat or inhibit pathological conditions associated with inflammatory response
发明人：TRIPP MATTHEW L; BABISH JOHN G; BLAND JEFFREY S; DARLAND GARY K; LERMAN ROBERT; LUKACZER DANIEL O; LISKA DEANN J; HOWELL TERRENCE
权利人:TRIPP MATTHEW L; BABISH JOHN G; BLAND JEFFREY S; DARLAND GARY K; LERMAN ROBERT; LUKACZER DANIEL O; LISKA DEANN J; HOWELL TERRENCE; METAPROTEOMICS LLC
摘要:A natural formulation of compounds that would to modulate inflammation is disclosed. The formulation would also inhibit expression of COX-2, inhibit synthesis of prostaglandins selectively in target cells, and inhibit inflammatory response selectively in target cells. The compositions containing at least one fraction isolated or derived from hops. Other embodiments relate to combinations of components, including at least one fraction isolated or derived from hops, tryptanthrin and conjugates thereof, rosemary, an extract or compound derived from rosemary, a triterpene species, or a diterpene lactone or derivatives or conjugates thereof.

专利号:US-7431948-B2
优先权日:2001-06-20
标 题:Compositions that treat or inhibit pathological conditions associated with inflammatory response
发明人：TRIPP MATTHEW L; BABISH JOHN G; BLAND JEFFREY S; DARLAND GARY K; LERMAN ROBERT; LUKACZER DANIEL O; LISKA DEANN J; HOWELL TERRENCE
权利人:METAPROTEOMICS LLC
摘要:A natural formulation of compounds that would to modulate inflammation is disclosed. The formulation would also inhibit expression of COX-2, inhibit synthesis of prostaglandins selectively in target cells, and inhibit inflammatory response selectively in target cells. The compositions containing at least one fraction isolated or derived from hops. Other embodiments relate to combinations of components, including at least one fraction isolated or derived from hops, tryptanthrin and conjugates thereof, rosemary, an extract or compound derived from rosemary, a triterpene species, or a diterpene lactone or derivatives or conjugates thereof.

专利号:CN-114591277-A
优先权日:2022-02-28
标题 :A kind of benzene ring fused 5/6/7/6 tetracyclic compound and its synthesis method

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主要参考文献


1: Wu M, Qi H, Li J, Velu P, Han X. Rosmanol Alleviates Myocardial Ischemia- Reperfusion Injury by Enhancing the Myocardial miR-126/VEGF/PI3K/AKT Signaling in STZ-Induced Diabetic Rats. Comb Chem High Throughput Screen. 2024 Aug 26. doi: 10.2174/0113862073285839240808113152. Epub ahead of print.
151:107669. doi: 10.1016/j.bioorg.2024.107669. Epub 2024 Jul 23. 17(7):862. doi: 10.3390/ph17070862.
4: Athanasiadis V, Chatzimitakos T, Mantiniotou M, Kalompatsios D, Kotsou K, Makrygiannis I, Bozinou E, Lalas SI. Optimization of Four Different Rosemary Extraction Techniques Using Plackett-Burman Design and Comparison of Their Antioxidant Compounds. Int J Mol Sci. 2024 Jul 14;25(14):7708. doi: 10.3390/ijms25147708.

合成参考文献


参考文献:10.1007/s11130-011-0233-5
摘要:Doolaege EH, Raes K, De Vos F, Verhé R, De Smet S. Absorption, distribution and elimination of carnosic acid, a natural antioxidant from Rosmarinus officinalis, in rats. Plant Foods Hum Nutr. 2011 Jun;66(2):196–202. doi: 10.1007/s11130-011-0233-5.
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