CAS: 500-38-9; 4,4'-(2,3-Dimethylbutane-1,4-Diyl)Bis(Benzene-1,2-Diol)

该化合物是一种主要来自杂酚树(Larrea tridardata)的自然产生的酚类化合物,其特点是抗氧化性特性,这归因于它能够蒸发自由基和抑制脂肪过氧化性.NDGA的分子配方为C15H14O4, 具有复杂的结构,包括两个甲氧基组和一种食道动物.该化合物已经研究过其潜在的治疗用途,包括防炎和抗癌作用,尽管其使用因潜在的毒性和副作用而受到限制.据了解,NDGA具有抗微生物特性,并因其在食品保存方面的作用而受到调查.在溶性方面,它具有中性有机溶剂的溶解性,但在水方面则较少.由于它独特的化学结构和生物活动,NDGA仍然对药学研究和工业应用都感兴趣.然而,在处理这一化合物时,安全和管制因素至关重要.

结构式图片

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CAS号63-91-2 L-苯丙氨酸 | CAS号120-80-9 邻苯二酚

合成工艺路线路线简述

  • 合成目标产物 Nordihydroguaiaretic Acid 主要起始原料 Fw 358.2
  • (文献来源)合成步骤主要原料 Fw 358.2
📜2,6-二甲氧基-4-羟基苯甲醛置于氢溴酸体系中,用 水 作为反应溶剂,化学反应 10.0H,以91.26%的收率获得产物去甲二氢愈创木酸
参考文献:一种去甲二氢愈创木酸(ndga)新的合成方法
标题:一种去甲二氢愈创木酸(ndga)新的合成方法
摘要:去甲二氢愈创木酸具有广泛的生理活性和药理活性.本发明公开了一种去甲二氢愈创木酸新的合成方法,其包括以下步骤:以藜芦酮为原料,在催化剂的作用下发生还原偶联反应,得到频哪醇;频哪醇在质子酸或者路易斯酸催化下,被三烷基硅烷或者三芳基硅烷还原,反应生成1,4‑二(3,4‑二甲氧基苯基)‑2,3‑二甲基丁烷;最后在氢卤酸或者路易斯酸的作用下,醚键断裂,合成了去甲二氢愈创木酸.化合物结构用1H‑NMR表征.所用的原料和试剂易得,反应路线短,反应条件温和,产率较高,成本低廉,为工业化合成去甲二氢愈创木酸开辟一条简便的路径.

海关参考信息

专利信息


专利号:US-3906004-A
优先权日:1968-12-09
标题 :Stereoselective synthesis of intermediate for preparation of meso-nordihydroguaiaretic acid
发明人:PERRY CLARK WILLIAM
权利人:HOFFMANN LA ROCHE
摘要:This invention is directed to the stereoselective synthesis of the food additive meso-nordihydroguaiaretic acid from a protected ortho dihydroxy benzene and intermediates in this synthesis.

专利号:US-8304409-B2
优先权日:2002-07-03
标 题:Nitrosated nonsteroidal antiinflammatory compounds, compositions and methods of use
发明人:EARL RICHARD A; EZAWA MAIKO; FANG XINQIN; GARVEY DAVID S; GASTON RICKY D; KHANAPURE SUBHASH P; LETTS L GORDON; LIN CHIA-EN; RANATUNGE RAMANI R; RICHARDSON STEWART K; SCHROEDER JOSEPH D; STEVENSON CHERI A; WEY SHIOW-JYI
权利人:EARL RICHARD A; EZAWA MAIKO; FANG XINQIN; GARVEY DAVID S; GASTON RICKY D; KHANAPURE SUBHASH P; LETTS L GORDON; LIN CHIA-EN; RANATUNGE RAMANI R; RICHARDSON STEWART K; SCHROEDER JOSEPH D; STEVENSON CHERI A; WEY SHIOW-JYI; NICOX SA
摘要:The invention describes novel nitrosated nonsteroidal antiinflammatory drugs (NSAIDs) and pharmaceutically acceptable salts thereof, and novel compositions comprising at least one nitrosated NSAID, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel compositions comprising at least one nitrosated NSAID, and at least one compound that donates, transfers or releases nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor, stimulates endogenous synthesis of nitric oxide or is a substrate for nitric oxide synthase and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one nitrosated NSAID, and, optionally, at least one nitric oxide donor and/or at least one therapeutic agent. The invention also provides methods for treating inflammation, pain and fever; for treating gastrointestinal disorders; for facilitating wound healing; for treating and/or preventing gastrointestinal, renal and/or respiratory toxicities resulting from the use of nonsteroidal antiinflammatory compounds; for treating inflammatory disease states and/or disorders; and for treating and/or preventing ophthalmic diseases and/or disorders.

专利号:US-8828984-B2
优先权日:2012-11-19
标题:Gold(III) complexes containing N-heterocyclic carbene ligand, synthesis, and their applications in cancer treatment and thiol detection
发明人:CHE CHI MING; ZOU TAOTAO
权利人:UNIV HONG KONG; UNIV HONG KONG
摘要:Provided herein is a method of synthesis of Au(III)-NHC complexes, a pharmaceutical composition comprises thereof. Also provided herein are the methods for the treatment and prevention of cancer/tumor in patients in need thereof by the administration of the Au(III)-NHC complexes. Also provided is method of detecting thiol in a biological system. The Au(III)-NHC complexes possess anticancer activity such as the induction of cell death, inhibition of cellular proliferation, inhibition of thioredoxin reductase activity, and inhibition of tumor growth in vivo.

专利号:US-10577387-B1
优先权日:2018-08-09
标题 :Platinum (II) complexes containing N-heterocyclic carbene ligand and pincer ligands, synthesis, and their applications in cancer treatment
发明人:CHE CHI MING; Fung Sin Ki; Chen tian feng
权利人:UNIV HONG KONG
摘要:Provided herein is a method of synthesis of Pt(II) complexes, a pharmaceutical composition comprises thereof. Also provided herein are the methods for the treatment and prevention of cancer/tumor in patients in need thereof by the administration of the Pt(II) complexes. Also provided is a method of detecting the Pt(II) complex in a biological system. Also provided is a method of making the Pt(II) complex The Pt(II) complexes possess anticancer activity such as the induction of cell death, inhibition of cellular proliferation, and inhibition of tumor growth in vivo.

专利号:EP-1382327-A1
优先权日:2002-07-17
标 题 :Method of protection of the skin against ageing
发明人:DANOUX LOUIS; FREIS OLGA; PAULY GILLES
权利人:COGNIS FRANCE SA
摘要:A method for the production of means for the stimulation of human is proposednSkin cells as well as to protect against skin aging and damaging influencesnEnvironmental toxins and UV radiation, characterized in that the means at least onenSubstance containing the synthesis of energy donors of the mitochondrial respiratory chainnincreases while at the same time the rate of reactive oxygen species (ROS) innCell metabolism lowers.n n n Furthermore, the use of cosmetic and / or pharmaceutical preparations,ncontaining at least one substance which the synthesis of energy donorsnthe mitochondrial respiratory chain increases while at the same time the rate of reactive oxygen speciesn(ROS) in cell metabolism, to stimulate human skin cellsnas well as to the protection against skin aging and damaging influences by environmental poisons andnUV radiation proposed.

专利号:US-7211598-B2
优先权日:2002-06-28
标 题:Oxime and/or hydrozone containing nitrosated and/or nitrosylated cyclooxygenase-2 selective inhibitors, compositions and methods of use
发明人:GARVEY DAVID S; RANATUNGE RAMANI R; RICHARDSON STEWART K
权利人:NITROMED INC
摘要:The invention describes novel cyclooxygenase 2 (COX-2) selective inhibitors having at least one oxime group or hydrazone group and novel compositions comprising at least one cyclooxygenase 2 (COX-2) selective inhibitor having at least one oxime group or hydrazone group, and, optionally, at least one compound that donates, transfers or releases nitric oxide, stimulates endogenous synthesis of nitric oxide, elevates endogenous levels of endothelium-derived relaxing factor or is a substrate for nitric oxide synthase, and/or at least one therapeutic agent. The invention also provides novel kits comprising at least one COX-2 selective inhibitor having at least one oxime group or hydrazone group, optionally nitrosated and/or nitrosylated, and, optionally, at least one nitric oxide donor, and/or, optionally, at least one therapeutic agent. The novel cyclooxygenase 2 selective inhibitors of the invention having at least one oxime group or hydrazone group can be optionally nitrosated and/or nitrosylated. The invention also provides methods for treating inflammation, pain and fever; for treating and/or improving the gastrointestinal properties of COX-2 selective inhibitors; for facilitating wound healing; for treating and/or preventing renal and/or respiratory toxicity; for treating and/or preventing other disorders resulting from elevated levels of cyclooxygenase-2; and for improving the cardiovascular profile of COX-2 selective inhibitors.

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品牌试剂参考报价(招募中)

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主要参考文献


1: Díaz-Gerevini GT, Daín A, Pasqualini ME, López CB, Eynard AR, Repossi G. Diabetic encephalopathy: beneficial effects of supplementation with fatty acids ω3 and nordihydroguaiaretic acid in a spontaneous diabetes rat model. Lipids Health Dis. 2019 Feb 8;18(1):43. doi: 10.1186/s12944-018-0938-7.
2: Awasthi S, Preethy R, Saraswathi NT. Nordihydroguaiaretic acid prevents glycation induced structural alterations and aggregation of albumin. Int J Biol Macromol. 2019 Feb 1;122:479-484. doi: 10.1016/j.ijbiomac.2018.10.173. Epub 2018 Oct 26. doi: 10.1016/j.enzmictec.2018.10.002. Epub 2018 Oct 5. doi: 10.1111/bph.14528. Epub 2018 Dec 10.
5: Wang L, Li L, Quan MY, Wang D, Jia Z, Li ZF, Li B, Guo L, Tan GJ. Nordihydroguaiaretic acid can suppress progression of experimental autoimmune encephalomyelitis. IUBMB Life. 2018 May;70(5):432-436. doi: 10.1002/iub.1739. Epub 2018 Apr 10. doi: 10.1124/jpet.117.243733. Epub 2018 Feb 22.

合成参考文献


参考文献:10.1007/s10549-005-9081-z
摘要:Altundag K, Altundag O, Karakaya E, Akyurek S. Overcoming trastuzumab resistance with nordihydroguaiaretic acid Breast Cancer Research and Treatment. 2005 Dec 01;96(3):301. doi: 10.1007/s10549-005-9081-z.
参考文献:10.1016/j.bmcl.2011.06.089
摘要:Ilić M, Kontogiorgis C, Hadjipavlou-Litina D, Ilaš J, Kikelj D. Thrombin inhibitors with lipid peroxidation and lipoxygenase inhibitory activities. Bioorganic & Medicinal Chemistry Letters. 2011 Aug;21(16):4705–9. doi: 10.1016/j.bmcl.2011.06.089.
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