CAS: 95809-78-2; 6,8-Bis(Benzylthio)Octanoic Acid

该化合物是一种有机化合物,其特点是碳氢化合物链长,并且有硫醚功能组,结构上有两个与辛醇酸脊相连的苯甲基硫酸组,这有其独特的化学特性.由于长烷基链长,该化合物可能表现出疏水特性,而苯基组则能够提供更多的芳香相互作用.硫醚联系可能会影响其在不同溶剂中的再活性和溶性.作为脂肪酸衍生物,它可以参与生物化学过程,或者在工业应用中充当表面活性剂或乳化剂.生物系统中的具体应用和行为将取决于其与其他分子的相互作用,包括蛋白和膜.安全数据和处理预防措施应当与任何化学物质一样,特别是具有潜在生物活动或毒性的物质一样加以考虑.

结构式图片

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CAS号100-53-8 苄硫醇 | CAS号36915-02-3 sodium,6,8-bis(... | CAS号100-39-0 溴化苄 | CAS号100-44-7 氯化苄

合成工艺路线路线简述

  • 101577-85-9 = 95809-78-2
    反应条件:1.1 Reagents: Hydrochloric Acid Solvents: Ethanol
    标题:α-Lipoic Acid And Its Related Compounds. I. Synthesis Of Dl-α-Lipoic Acid
    作者:Nakano,Isamu; Sano,Mitsuji
    参考文献:Yakugaku Zasshi 日期:1955 卷标:75 页码:1296-8]

    = 95809-78-2 [标题:Reaction Conditions
    标题:Pharmaceutical Composition Of Lipoic Acid Derivatives
    参考文献:World Intellectual Property Organization]

    1077-28-7 = 95809-78-2
    反应条件:1.1 Reagents: Sodium Hydroxide Solvents: Water; 20 - 25 °C; 25 °C -> 40 °C1.2 Reagents: Sodium Borohydride; 1 H,< 60 °C; 1 H,< 60 °C1.3 Reagents: Sodium Hydroxide Solvents: Water; 1 H,< 50 °C; 1 H,< 50 °C1.4 Reagents: Hydrochloric Acid Solvents: Water; < Ph 2
    标题:An Efficient,Economical Synthesis Of The Novel Anti-Tumor Agent Cpi-613
    作者:Gibson,Frank S.; Gupta,Deepak; Shorr,Robert; Rodriguez,Robert
    参考文献:Organic Process Research & Development 日期:2011 卷标:15(4) 页码:855-857]

    1077-28-7 = 95809-78-2
    反应条件:1.1 Reagents: Sodium Hydroxide,Sodium Borohydride; 1 H,Rt -> 40 °C1.2 Reagents: Sodium Hydroxide Solvents: Water; 40 °C; Cooled1.3 Reagents: Hydrochloric Acid Solvents: Water; Ph 1 - 2
    标题:Method For Synthesizing Devimistat
    参考文献:China]

    1070-64-0 = 95809-78-2
    反应条件:1.1 Reagents: Potassium Hydroxide,Sodium Solvents: Ethanol
    标题:Syntheses Of Dl-α-Lipoic Acid
    作者:Reed,Lester J.; Niu,Ching-I
    参考文献:Journal Of The American Chemical Society 日期:1955 卷标:77 页码:416-19]

    408337-78-0 = 95809-78-2 [标题:Reaction Conditions
    标题:Syntheses Of Dl-α-Lipoic Acid
    作者:Soper,Quentin F.; Buting,Walter E.; Cochran,James E. Jr.; Pohland,Albert
    参考文献:Journal Of The American Chemical Society 日期:1954 卷标:76 页码:4109-12]

    = 95809-78-2 [标题:Reaction Conditions
    标题:Substituted Thiol-Containing Alkyl Fatty Acids And Process For Synthesizing Derivatives Thereof
    参考文献:World Intellectual Property Organization]

    = 95809-78-2 [标题:Reaction Conditions
    标题:Modulation Of Enzymatic Structure,Activity,And/or Expression Level
    参考文献:World Intellectual Property Organization
Dihydrothioctic Acid Sodium Salt 以90的收率获得产物6,8-双(苄基硫代)辛酸
参考文献:Lipoic Acid Derivatives
标题:Lipoic Acid Derivatives
摘要:含有硫辛酸衍生物的制剂和药物制剂在治疗和预防疾病方面非常有用,这些疾病的特征是疾病细胞对硫辛酸衍生物敏感.

海关参考信息

专利信息


专利号:WO-2023144235-A1
优先权日:2022-01-27
标 题 :Methods for monitoring and treating warburg effect in patients with pi3k-related disorders
发明人:CANAUD GUILLAUME; LADRAA SOPHIA
权利人:INST NAT SANTE RECH MED; ASSIST PUBLIQUE HOPITAUX PARIS APHP; CENTRE NAT RECH SCIENT; UNIV PARIS CITE
摘要:Using a unique tool of PROS, they demonstrate that PIK3CA mutation leads to GLUT4 membrane accumulation with a negative feedback loop on insulin secretion, a burst of liver IGFBP1 synthesis with IGF1 sequestration and low circulating levels. They further show that AKT2 drives a large part of the phenotype. In addition, they demonstrate for the first time that a single PIK3CA mutation induces metabolic reprogramming with the Warburg effect and protein and lipid synthesis—hallmarks of cancer cells—in vitro, in vivo and in patients. They finally show that alpelisib, an approved PIK3CA inhibitor in oncology, is efficient at preventing and improving PIK3CA-adipose tissue overgrowth and reversing metabolomic anomalies in both animal models and patients. Accordingly, the present invention relates to an in vitro method for monitoring the efficiency of a PI3K inhibitor treatment in a subject in need thereof comprising the step of determining the level of at least one metabolite selected in the group consisting of cis-aconitate, succinic acid, 5-methylcytosine, acetyl-carnitine, acetyl-lysine, argininosuccinate, betaine, butyric acid, carnitine, creatine, glucose, glycine, hexanoyl-carnitine, L-fucose, lactate, L-dihydroorotic acid, linolenic acid, nicotinamide N-oxide, palmitoyl-carnitine, panthotenate, pyruvate, quinolinic acid, tryptophan, urate, in a biological sample obtained from the subject.
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主要参考文献


1: Vasan K, Werner M, Chandel NS. Mitochondrial Metabolism as a Target for Cancer Therapy. Cell Metab. 2020 Sep 1;32(3):341-352. doi: 10.1016/j.cmet.2020.06.019. Epub 2020 Jul 14.
2: Anderson R, Miller LD, Isom S, Chou JW, Pladna KM, Schramm NJ, Ellis LR, Howard DS, Bhave RR, Manuel M, Dralle S, Lyerly S, Powell BL, Pardee TS. Phase II trial of cytarabine and mitoxantrone with devimistat in acute myeloid leukemia. Nat Commun. 2022 Mar 30;13(1):1673. doi: 10.1038/s41467-022-29039-4.
3: Mohan A, Griffith KA, Wuchu F, Zhen DB, Kumar-Sinha C, Crysler O, Hsiehchen D, Enzler T, Dippman D, Gunchick V, Achreja A, Animasahun O, Choppara S, Nenwani M, Chinnaiyan AM, Nagrath D, Zalupski MM, Sahai V. Devimistat in Combination with Gemcitabine and Cisplatin in Biliary Tract Cancer: Preclinical Evaluation and Phase Ib Multicenter Clinical Trial (BilT-04). Clin Cancer Res. 2023 Jul 5;29(13):2394-2400. doi: 10.1158/1078-0432.CCR-23-0036.

合成参考文献


参考文献:10.1007/s00109-011-0785-8
摘要:Zachar Z, Marecek J, Maturo C, Gupta S, Stuart SD, Howell K, Schauble A, Lem J, Piramzadian A, Karnik S, Lee K, Rodriguez R, Shorr R, Bingham PM. Non-redox-active lipoate derivates disrupt cancer cell mitochondrial metabolism and are potent anticancer agents in vivo. J Mol Med (Berl). 2011 Nov;89(11):1137–48. doi: 10.1007/s00109-011-0785-8.
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