CAS: 580-72-3; (3R,4R)-3,4-Bis(4-Hydroxy-3-Methoxybenzyl)Dihydrofuran-2(3H)-One
该化合物是自然产生的离子体,存在于各种植物来源,包括麻痹籽和芝麻籽种子中,被确认为作为甲状腺素的前体,如二甲醇和甲状腺素,具有植物性能和抗氧化性特性; Matailsinol 因其潜在生物活性效应,包括调制激素代谢和细胞氧化性压力,对研究感兴趣;其化学稳定性和生物利用率使其成为营养,药理学和预防健康研究的宝贵化合物;甲状腺素的分析标准用于HPLC和LC-MS的复杂基质精确量化应用;该化合物通常以高纯度形式供应实验室和调查用途.
- 英文名称(3R,4R)-3,4-Bis(4-Hydroxy-3-Methoxybenzyl)Dihydrofuran-2(3H)-One
- 中文名称(αR,βR)-α,β-双(4-羟基-3-甲氧苯基)丁内酯
- IUPAC名称(3R,4R)-3,4-bis(4-hydroxy-3-methoxybenzyl)dihydrofuran-2(3H)-one
- 其它别名Matairesinol, >=85% (Hplc); Dihydro-3,4-Bis[(4-Hydroxy-3-Methoxyphenyl)Methyl]-(3R,4R)-2(3H)-Furanone; (-)-Matairesinol; Unii-Xlw63P8Wua; 2
- CAS编号580-72-3
- MFCD编号:MFCD00792569
- FDA UNII编号:XLW63P8WUA
- 分子式:C20H22O6分子量:358.39
- 产品CID: 1555662
- 产品分类天然产物 → 木脂素
物理性质
- 熔点119～120°C
- 沸点593.0±45.0 °C at 760 mmHg
- 闪点212.3±22.2 °C
- 密度1.3±0.1 g/cm3
- pKa:10.02±0.20(预测)
- PSA:85.22
- LogP:1.7
- 折射率1.605
- 蒸汽压0.0±1.7 mmHg at 25°C
- 溶解性Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly)
- 外观形态粉末
- 储存条件2-8°C
- 产品应用该化合物用作分析标准;它在一个小鼠外皮皮炎模型中表现出抗过敏效应;MATAIRESINOL的时事应用扭转了在DFE引起的NC/NGA小鼠耳中IL-4和IFN-GNMRNA表达方式的变化.
MSDS等安全信息
上下游产品
matairesinol 4'-O-β-gentiobioside (3R,4R)-3,4-bis(4-benzyloxy-3-methoxybenzyl)dihydrofuran-2(3H)-one ethyl acetate RS)-3c-hydroxymethyl-3r,4ξ-divanillyl-dihydro-furan-2-one(3RS)-3c-hydroxymethyl-3r,4ξ-divanillyl-dihydro-furan-2-one3-methoxy-4-hydroxybenzoic acid vanillin dimethylmatairesinol (-)-(2R,3R)-2-(3',4'-dihydroxybenzyl)-3-(3'',4''-dihydroxybenzyl)butyrolactone合成工艺路线路线简述
📜3-(4-羟基-3-甲氧基苯基)丙酸置于2,6-二甲基吡啶,Sodium Periodate,四氧化锇,锂硼氢,正丁基锂,Palladium 10% On Activated Carbon,水,氢气,Sodium Hexamethyldisilazane,双(三甲基硅烷基)氨基钾,Potassium Carbonate,三乙胺,Potassium Hydroxide体系中,用 四氢呋喃,1,4-二氧六环,甲醇,乙醚,正己烷,水,乙酸乙酯,丙酮,苯 作为反应溶剂,-78.0~70.0 °C,101.33 Kpa 条件下,反应 30.42H,反应生成 外消旋马台树脂醇
参考文献:手性β-苄基-γ-丁内酯的获取及其在对映体纯(+)-异豆香脂醇,(-)-异豆香脂醇和(-)-肠内酯的合成中的应用
标题:手性β-苄基-γ-丁内酯的获取及其在对映体纯(+)-异豆香脂醇,(-)-异豆香脂醇和(-)-肠内酯的合成中的应用
摘要:通过高立体选择性会聚合成法合成了癸二异胡香脂树脂醇对映体和对映体纯(-)-内酯.evans非对映选择性烷基化,然后是新形成的旋光性β-苄基-γ-丁内酯的底物诱导的非对映选择性α-烷基化,形成了目标骨架的β-β'键.癸二异戊二烯树脂醇的(s,S)-和(r,R)-对映异构体和(-)-对内酯的总产率分别为12-14%(11步)和20%(7步). 全合成-天然产物-内酯-不对称-非对映选择性烷基化
DOI:10.1055/s-0030-1259982
海关参考信息
- 2902600000-乙苯
2905121000-正丙醇
2907210001-间苯二酚
2909110000-乙醚 - 💡 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-2018105546-A1
优先权日:2011-06-14
标题:Methods for Chemical Synthesis of Biologically Active Compounds Using Supramolecular Protective Groups and Novel Compounds Obtainable Thereby
专利号:US-2014243280-A1
优先权日:2011-06-14
标题:Methods for chemical synthesis of biologically active compounds using supramolecular protective groups and novel compounds obtainable Thereby
专利号:WO-2004069774-A2
优先权日:2003-02-04
标题 :Synthesis of 13c-labelled estrogen analogues
专利号:EP-2721046-A1
优先权日:2011-06-14
标题:Methods for chemical synthesis of biologically active compounds using supramolecular protective groups and novel compounds obtainable thereby
专利号:WO-2012173477-A1
优先权日:2011-06-14
标题 :Methods for chemical synthesis of biologically active compounds using supramolecular protective groups and novel compounds obtainable thereby
专利号:EP-2721046-B1
优先权日:2011-06-14
标题 :Methods for chemical synthesis of biologically active compounds using supramolecular protective groups and novel compounds obtainable thereby
发明人：HERRMANN ANDREAS; BASTIAN ANDREAS ALEXANDER; MARCOZZI ALESSIO
权利人:UNIV GRONINGEN
供应商参考报价(招募中)
品牌试剂参考报价(招募中)
📌 第三方产品分析报告
主要参考文献
1: Mahajan M, Suryavanshi S, Bhowmick S, Alasmary FA, Almutairi TM, Islam MA, Kaul-Ghanekar R. Matairesinol, an active constituent of HC9 polyherbal formulation, exhibits HDAC8 inhibitory and anticancer activity. Biophys Chem. 2021 Jun;273:106588. doi: 10.1016/j.bpc.2021.106588. Epub 2021 Apr 2.
345:577286. doi: 10.1016/j.jneuroim.2020.577286. Epub 2020 Jun 6. 42(10):2850-2860. doi: 10.1007/s11064-017-2301-1. Epub 2017 May 17.
14:35. doi: 10.1186/1472-6882-14-35.
合成参考文献
摘要:S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198
参考文献:10.2460/ajvr.2004.65.592
摘要:Cerundolo R, Court MH, Hao Q, Michel KE. Identification and concentration of soy phytoestrogens in commercial dog foods. Am J Vet Res. 2004 May;65(5):592–6. doi: 10.2460/ajvr.2004.65.592.
参考文献:10.1016/j.anaerobe.2005.11.002
摘要:Clavel T, Borrmann D, Braune A, Doré J, Blaut M. Occurrence and activity of human intestinal bacteria involved in the conversion of dietary lignans. Anaerobe. 2006 Jun;12(3):140–7. doi: 10.1016/j.anaerobe.2005.11.002.
参考文献:10.1271/bbb.100781
摘要:YAMAWAKI M, NISHI K, NISHIMOTO S, YAMAUCHI S, AKIYAMA K, KISHIDA T, MARUYAMA M, NISHIWAKI H, SUGAHARA T. Immunomodulatory Effect of (−)-Matairesinolin Vivoandex Vivo. Bioscience, Biotechnology, and Biochemistry. 2011 May 23;75(5):859–63. doi: 10.1271/bbb.100781.
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