CAS: 592-95-0; 4-Isothiocyanato-1-(Methylsulfinyl)But-1-Ene

该化合物是一种自然形成的化合物,被归类为异硫氰酸盐,主要产自西兰花和布鲁塞尔芽芽等十字架蔬菜,以其潜在的健康利益而著称,特别是其抗氧化剂和抗炎特性;该化合物的特点是其含有硫的功能组,该组有助于其生物活动;对硫磷进行了研究,以确定其在癌症预防中的作用,因为它可能诱发二阶段解毒酶,促进癌症细胞中的聚变;此外,该化合物具有抗微生物特性,并可能支持心血管健康;该化合物通常位于植物来源的低浓度中,其稳定性可能受到温度和pH等因素的影响.作为异硫氰酸化合物家族的成员,硫磷与硫磷等其他化合物具有结构相似性,但具有明显的生物影响.研究继续探索其行动机制和潜在治疗应用机制,使其成为营养科学和药理学的主体.

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CAS号51598-96-0 4-(METHYLTHIO)-... | CAS号28463-24-3 glucoraphenin

合成工艺路线路线简述

    📜4-(甲硫基)-3-丁烯基异硫氰酸酯置于双氧水体系中,用 甲醇 作为反应溶剂,化学反应生成 莱菔素
    参考文献:Cytotoxic And Antioxidant Activity Of 4-Methylthio-3-Butenyl Isothiocyanate From Raphanus Sativus L. (Kaiware Daikon) Sprouts
    标题:Cytotoxic And Antioxidant Activity Of 4-Methylthio-3-Butenyl Isothiocyanate From Raphanus Sativus L. (Kaiware Daikon) Sprouts
    摘要:There Is High Current Interest In The Chemopreventive Potential Of Brassica Vegetables (Cruciferae),Particularly Due To Their Content In Glucosinolates (Gl),Which Upon Myrosinase Hydrolysis,Release The Corresponding Isythiocyanates (Itc). Some Itcs,Such As Sulforaphane (Sfn) From Broccoli (Brassica Oleacea Italica),Have Been Found To Possess Anticancer Activity Through Induction Of Apoptosis In Selected Cell Lines,As Well As Indirect Antioxidant Activity Through Induction Of Phase 11 Detoxifying Enzymes. Japanese Daikon (Raphanus Sativus L.) Is Possibly The Vegetable With The Highest Per Capita Consumption Within The Brassicaceae Family. Thanks To A Recently Improved Gram Scale Production Process,It Was Possible To Prepare Sufficient Amounts Of The Gl Glucoraphasatin (Grh) As Well As The Corresponding Itc 4-Methylthio-3-Butenyl Isothiocyanate (Grh-Itc) From Its Sprouts. This Paper Reports A Study On The Cytotoxic And Apoptotic Activities Of Grh-Itc Compared With The Oxidized Counterpart 4-Methylsulfinyl-3-Butenyl Isothiocyanate (Gre-Itc) On Three Human Colon Carcinoma Cell Lines (Lovo,Hct-116,And Ht-29) Together With A Detailed Kinetic Investigation Of The Direct Antioxidant/radical Scavenging Ability Of Grh And Grh-Itc. Both Grh-Itc And Gre-Itc Reduced Cell Proliferation In A Dose-Dependent Manner And Induced Apoptosis In The Three Cancer Cell Lines. The Compounds Significantly (P < 0 05) Increased Bax And Decreased Bcl2 Protein Expression,As Well As Producing Caspase-9 And Parp-1 Cleavage After 3 Days Of Exposure In The Three Cancer Cell Lines. Grh-Itc Treatment Was Shown To Have No Toxicity With Regard To Normal Human Lymphocytes (-15 +/-5%) In Comparison With Sfn (Complete Growth Inhibition). Grh And Grh-Itc Were Able To Quench The 2,2-Diphenyl-1-Picrylhydrazyl Radical,With Second-Order Rate Constants Of 14.0 +/-2.8 And 43.1 +/-9.5 M-1 S(-1),Respectively (At 298 K In Methanol),Whereas The Corresponding Value Measured Here For The Reference Antioxidant Alpha-Tocopherol Was 425 +/-40 M-1 S(-1). Grh Reacted With H2O2 And Tert-Butyl Hydroperoxide In Water (Ph 7.4) At 37 Degrees C,With Rate Constants Of 1.9 +/-0.3 X 10(-2) And 9.5 +/-0.3 X 10(-4) M-1 S(-1) (Paralleling Recently Developed Synthetic Antioxidants) Being Quantitatively (>97%) Converted To Gre. It Is Demonstrated That Grh-Itc Has Interesting Antioxidant/radical Scavenging Properties,Associated With A Selective Cylotoxic/apoptotic Activity Toward Three Human Colon Carcinoma Cell Lines,And Very Limited Toxicity On Normal Human T-Lymphocytes.
    DOI:10.1021/jf073123C

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    专利信息


    专利号:WO-2025069039-A1
    优先权日:2023-09-28
    标题:An in situ process for the preparation of primary amine compounds
    发明人:SAMANT RAJARAM; TONGRA MANOJ
    权利人:SAMANT RAJARAM; TONGRA MANOJ
    摘要:An in situ process for the preparation of primary amine compounds The invention disclosed herein relates to an in situ process for the preparation of primary amine compounds. Particularly, it relates to the preparation of primary amine compounds having general Formula (I). Formula (I) wherein n is 1 to 9 and X is -S, -N- or -O. More particularly, the present invention relates to the preparation of primary amine compounds with high yield and purity which is further used as potent intermediate in the synthesis of therapeutically active isothiocyanates (ITCs).

    专利号:CN-111034616-A
    优先权日:2019-12-25
    标题 :A method for the synthesis and release of glucoraphanin and sulforaphane in hairy roots of broccoli

    专利号:CN-102093273-B
    优先权日:2010-11-29
    标 题:A kind of chemical synthesis method of sulforaphane

    专利号:CN-102093273-A
    优先权日:2010-11-29
    标 题:A kind of chemical synthesis method of sulforaphane

    专利号:CN-111034616-B
    优先权日:2019-12-25
    标 题:A method for the synthesis and release of glucoraphanin and sulforaphane in hairy roots of broccoli

    专利号:CN-105001135-B
    优先权日:2015-07-10
    标题:A kind of chemical synthesis method of raphacin

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    主要参考文献


    1: Gao R, Liu P, Bi J, Jiang Y, Zhao T, Yuan X, Zhang C, Wang Y. The Effects of Different Thiol-Containing Compounds on the Degradation of Sulforaphene. Molecules. 2024 Sep 12;29(18):4328. doi: 10.3390/molecules29184328.
    2: Zhu Q, Zhang P, Liu D, Tang L, Yu J, Zhang C, Jiang G. Glucosinolate extract from radish (Raphanus sativus L.) seed attenuates high-fat diet-induced obesity: insights into gut microbiota and fecal metabolites. Front Nutr. 2024 Aug 8;11:1442535. doi: 10.3389/fnut.2024.1442535.
    3: Zhao Z, Yuan Y, Li S, Wang X, Yang X. Natural compounds from herbs and nutraceuticals as glycogen synthase kinase-3β inhibitors in Alzheimer's disease treatment. CNS Neurosci Ther. 2024 Aug;30(8):e14885. doi: 10.1111/cns.14885.

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    参考文献:10.1038/s41592-019-0358-2]
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