CAS: 90-33-5; 7-Hydroxy-4-Methyl-2H-Chromen-2-One

该化合物是化学上惰性β-基托酸衍生物,对甘基氨基甘酸合成(GAG)具有重大抑制作用,其强大的抗诱变性特性已得到广泛研究,凸显了其在癌症治疗应用方面的潜力. 该产品为调整细胞过程提供了一种新的方法,对研究和治疗发展都有影响.

英文名称7-Hydroxy-4-Methyl-2H-Chromen-2-One
中文名称4-甲基伞形酮
IUPAC名称7-hydroxy-4-methyl-2H-chromen-2-one
其它别名4-Methyl Umbelliferone; Bilcolic; Cantabilin; Lm 94; 4 Methylumbelliferone; Medilla; Cas-90-33-5; 7-Hydroxy-4-Methyl Coumarin; 7-Hydroxy-4-Met
CAS编号90-33-5
MFCD编号:MFCD00006866
EINECS号:201-986-7
FDA UNII编号:3T5NG4Q468
分子式:C10H8O3
分子量:176.17
产品CID: 1935832
产品分类原料药 → 消化系统用药 → 利胆药

相似结构搜索
InChIKey: HSHNITRMYYLLCV-UHFFFAOYSA-N
InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3…
计算化学: 氢键受体数3.0氢键供体数1.0可旋转键数0.0

物理性质

熔点188.5-190 °C(文献)
沸点377.4 °C at 760 mmHg
闪点174.5 °C
密度1.319 g/cm3
PH:Green 1 uorescent (0.0) to weak blue 1 uorescent (2.0);Weak blue 1 uorescent (6.5) blue 1 uorescent (8.0)
pKa:7.79(at 25°C)
PSA:50.44
LogP:1.807
折射率1.5036 (估算)
蒸汽压0.00000724 [mmHg]
溶解性Practically Insoluble In Water; Slightly Soluble In Ethanol, Ether,Chloroform; Soluble Inmethanol
敏感性Stable. Combustible. Incompatible with strong oxidizing agents.
外观形态类白色至黄色结晶粉末
储存条件2-8°C
产品应用该品为利胆药,又是抗过敏药色甘酸钠的中间体.
性质描述针状体结晶.熔点185-186°C(194-195°C)溶于乙醇,乙酸,碱溶液和氨,微溶于热水,乙醚和氯仿.与浓硫酸作用呈蓝色荧光.

MSDS等安全信息

GHS象形图
GHS符号GHS07;
注释: Exclamation mark
危险类别皮肤腐蚀/刺激类别2
严重眼刺激类别2
急性毒性类别4(吸入)
急性毒性类别4(经皮)
急性毒性类别4(经口)
特定目标器官毒性 - 单次接触类别3
水生慢性毒性类别3
严重眼刺激类别2A
警示词Warning(警告)
危险描述H315 |造成皮肤刺激.
H319 |造成严重眼刺激.
H332 |吸入有害.
H312 |皮肤接触有害.
H302 |吞咽有害.
H335 |可能引起呼吸道刺激.
H412 |对水生生物有害并具有长期持续影响.
防范说明P261-P280a-P304+P340-P305+P351+P338-P405-P501a
UN编号NONH for all modes of transport
危险品标志Xi,Xn
风险等级Irritant
安全声明26-37/39-36
危险类别码36/37/38-20/21/22
WGK Germany2

欧盟法规

ECHA物质C&L通报REACH预注册

上下游产品

合成工艺路线路线简述

141-97-9 = 90-33-5
反应条件:1.1 Reagents: Sulfuric Acid Solvents: Water
标题:Synthesis And Antimicrobial Activity Of 7-[(5-(Mercapto)-1,3,4-Oxadiazol-2-Yl)Methoxy]-4-Methyl-2H-Chromen-2-Ones
作者:Jadhav,Rahul P.; Patil,Sachin V.; Gosavi,Shraddha S.; Mhaske,Pravin C.; Raundal,Hemant N.; Et Al
参考文献:Indian Journal Of Heterocyclic Chemistry 日期:2010 卷标:20(1) 页码:25-28]

141-97-9 = 90-33-5
反应条件:1.1 Catalysts: P-Toluenesulfonic Acid
标题:Ptsa Catalyzed Clean And Efficient Synthesis Of 7-Hydroxy-4-Methylcoumarin Under Microwave Irradiation
作者:Mogilaiah,K.; Reddy,N. Vasudeva; Prashanthi,M.; Reddy,G. Randheer; Reddy,Ch. Srinivas
参考文献:Indian Journal Of Heterocyclic Chemistry 日期:2002 卷标:11(4) 页码:343-344]

141-97-9 = 90-33-5
反应条件:1.1 Catalysts: Ethanol,2-(Dimethylamino)-,Sulfate (1:1); 3 H,90 °C
标题:Cholinium Ionic Liquids As Cheap And Reusable Catalysts For The Synthesis Of Coumarins Via Pechmann Reaction Under Solvent-Free Conditions
作者:Zhang,Yuehua; Zhu,Anlian; Li,Qianqian; Li,Lingjun; Zhao,Yang; Et Al
参考文献:Rsc Advances 日期:2014 卷标:4(44) 页码:22946-22950]

105-45-3 = 90-33-5
反应条件:1.1 Catalysts: Sulfuric Acid; 25 Min,100 °C
标题:Easy Access To Coumarin Derivatives Using Alumina Sulfuric Acid As An Efficient And Reusable Catalyst Under Solvent-Free Conditions
作者:Amoozadeh,Ali; Ahmadzadeh,Majid; Kolvari,Eskandar
参考文献:Journal Of Chemistry 日期:2013 卷标:767825]

141-97-9 = 90-33-5
反应条件:1.1 Catalysts: Methanesulfonic Acid,Silica Solvents: Octadecane; 2 H,160 °C
标题:Silica-Supported Methanesulfonic Acid - An Efficient Solid Bronsted Acid Catalyst For The Pechmann Reaction In The Presence Of Higher N-Alkanes
作者:Joshi,J.; Mishra,M. K.; Srinivasarao,M.
参考文献:Canadian Journal Of Chemistry 日期:2011 卷标:89(6) 页码:663-670]

141-97-9 = 90-33-5
反应条件:1.1 Catalysts: Sulfuric Acid
标题:Chromenone And Quinolinone Derivatives As Potent Antioxidant Agents
作者:Vats,Praveen; Hadjimitova,Vera; Yoncheva,Krassimira; Kathuria,Abha; Sharma,Antara; Et Al
参考文献:Medicinal Chemistry Research 日期:2014 卷标:23(11) 页码:4907-4914]

141-97-9 = 90-33-5
反应条件:1.1 Solvents: Trifluoroacetic Acid; Rt; 30 Min,100 °C; Cooled; 30 Min,Rt
标题:Establishing A Flow Process To Coumarin-8-Carbaldehydes As Important Synthetic Scaffolds
作者:Zak,Jaroslav; Ron,David; Riva,Elena; Harding,Heather P.; Cross,Benedict C. S.; Et Al
参考文献:Chemistry - A European Journal 日期:2012 卷标:18(32) 页码:9901-9910]

141-97-9 = 90-33-5
反应条件:1.1 Catalysts: Aluminum Chloride Solvents: Nitrobenzene; 100 - 130 °C1.2 Reagents: Sulfuric Acid Solvents: Water; 0 - 10 °C
标题:Synthesis And Antioxidant Activity Of Selected 4-Methylcoumarins
作者:Cavar,Sanja; Kovac,Franci; Maksimovic,Milka
参考文献:Food Chemistry 日期:2009 卷标:117(1) 页码:135-142]

141-97-9 = 90-33-5
反应条件:1.1 Reagents: Sulfuric Acid Solvents: Water
标题:Novel Thiocoumarins As Inhibitors Of Tnf-α Induced Icam-1 Expression On Human Umbilical Vein Endothelial Cells (Huvecs) And Microsomal Lipid Peroxidation
作者:Kumar,Sarvesh; Singh,Brajendra K.; Kalra,Neerja; Kumar,Vineet; Kumar,Ajit; Et Al
参考文献:Bioorganic & Medicinal Chemistry 日期:2005 卷标:13(5) 页码:1605-1613]

87-05-8 = 90-33-5
反应条件:1.1 Solvents: Water
标题:Biotransformations Of 4-Methylumbelliferone Derivatives - Fungal Mediated O-Dealkylations
作者:Kumar,K. Anil; Kumar,B. S. Vijay; Laxminarayana,B.; Ananthanarayanan,S.
参考文献:Studies In Surface Science And Catalysis 日期:1998 卷标:113 页码:541-546]

141-97-9 = 90-33-5
反应条件:1.1 Catalysts: Silica; 45 Min,110 °C
标题:Functionalizing Hy Zeolite With Sulfonic Acid,A Micro-Meso Structure Reusable Catalyst For Organic Transformations
作者:Zendehdel,Mojgan; Tavakoli,Fatemeh
参考文献:Journal Of The Iranian Chemical Society 日期:2022 卷标:19(4) 页码:1095-1107]

141-97-9 = 90-33-5
反应条件:1.1 Catalysts: (3-Mercaptopropyl)Trimethoxysilane; 1 H,120 °C1.2 Solvents: Ethanol; 15 Min,120 °C
标题:Competent,Selective And High Yield Of 7-Hydroxy-4-Methyl Coumarin Over Sulfonated Mesoporous Silica As Solid Acid Catalysts
作者:Khder,Abd El Rahman S.; Ahmed,Saleh A.; Khairou,Khalid S.; Altass,Hatem M.
参考文献:Journal Of Porous Materials 日期:2018 卷标:25(1) 页码:1-13]

141-97-9 = 90-33-5
反应条件:1.1 Catalysts: Hydrochloric Acid; 5 Min,100 °C
标题:4-Methylcoumarins With Cytotoxic Activity Against T24 And Rt4 Human Bladder Cancer Cell Lines
作者:Vianna,D. R.; Ruschel,L.; Dietrich,F.; Figueiro,F.; Morrone,F. B.; Et Al
参考文献:Medchemcomm 日期:2015 卷标:6(5) 页码:905-911]

141-97-9 = 90-33-5
反应条件:1.1 Catalysts: Iron Chloride (Fecl3); 12 H,70 °C
标题:Fecl3-Catalysed Ultrasonic-Assisted,Solvent-Free Synthesis Of 4-Substituted Coumarins. A Useful Complement To The Pechmann Reaction
作者:Prousis,Kyriakos C.; Avlonitis,Nicolaos; Heropoulos,Georgios A.; Calogeropoulou,Theodora
参考文献:Ultrasonics Sonochemistry 日期:2014 卷标:21(3) 页码:937-942]

141-97-9 = 90-33-5
反应条件:1.1 Catalysts: Zirconium Dioxide (Borated,Sulfated,Phosphated); 6 H,120 - 150 °C; 150 °C -> Rt
标题:Clean And Efficient Synthesis Of Coumarins Over Modified Metal Oxides Via Pechmann Reaction
作者:D'Souza,Joyce; Nagaraju,N.
参考文献:Indian Journal Of Chemical Technology 日期:2008 卷标:15(3) 页码:244-251]

141-97-9 = 90-33-5
反应条件:1.1 15 Min,150 °C
标题:Microwave-Assisted Solvent Free Synthesis Of Hydroxy Derivatives Of 4-Methyl Coumarin Using Nano-Crystalline Sulfated-Zirconia Catalyst
作者:Tyagi,Beena; Mishra,Manish K.; Jasra,Raksh V.
参考文献:Journal Of Molecular Catalysis A: Chemical 日期:2008 卷标:286(1-2) 页码:41-46]

105-45-3 = 90-33-5
反应条件:1.1 Reagents: Borane,Trifluoro-,Dihydrate; 20 Min,60 °C
标题:Pechmann Reaction Promoted By Boron Trifluoride Dihydrate
作者:Stoyanov,Edmont V.; Mezger,Jochen
参考文献:Molecules 日期:2005 卷标:10(7) 页码:762-766]

141-97-9 = 90-33-5
反应条件:1.1 60 S,Heated
标题:Microwave Assisted,Fly Ash Catalyzed Synthesis Of Coumarin Derivatives: Green Approach
作者:Hebade,Madhav J.; Shimpi,Ravindra P.; Chavan,Omprakash S.
参考文献:Pharma Chemica 日期:2022 卷标:14(2) 页码:27-30]

141-97-9 = 90-33-5
反应条件:1.1 Catalysts: Piperazinium,1,4-Dimethyl-1,4-Bis(4-Sulfobutyl)-,Perchlorate (1:2); 19 Min,110 °C
标题:Solvent-Free Synthesis Of 4-Substituted Coumarins Catalyzed By Novel Bronsted Acidic Ionic Liquids With Perchlorate Anion: A Convenient And Practical Complementary Method For Pechmann Condensation
作者:Taib,Layla Ahmed; Keshavarz,Mosadegh; Parhami,Abolfath
参考文献:Reaction Kinetics 日期:2021 卷标:133(1) 页码:383-403

4-Methylumbelliferylphosphate置于bovine Serum Albumin体系中,化学反应生成羟甲香豆素
参考文献:设计和表征微流系统中固定化酶.
标题:设计和表征微流系统中固定化酶.
摘要:本文中,我们报告了含有表面固定酶的总分析微系统的制造,表征和使用.链霉亲和素缀合的碱性磷酸酶与涂在聚二甲基硅氧烷微通道和硼硅酸盐微毛细管内部的生物素化磷脂双层相连.通过在芯片上进行层流控制的稀释,可以快速测定多种底物浓度下的酶动力学.这使得lineweaver-Burk分析可以从单个实验中同时收集所有数据进行.结果显示该异构系统的酶转换数为51.1 +/-3.2 S(-1).此外,扩展了相同的酶固定策略,以证明通过串联固定各种酶可以依次进行多种化学反应.具体地,通过使用固定的抗生物素蛋白d缀合的葡萄糖氧化酶和抗生蛋白链菌素缀合的辣根过氧化物酶的两个偶联步骤来检测葡萄糖的存在.
DOI:10.1021/ac010822U

海关参考信息

2908199090-其他酚的卤化衍生物
2908999090-其他酚的硝化衍生物
2918290000-其他含酚基羧酸
2905199090-其他饱和一元醇
💡 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-6479549-B2
优先权日:2000-02-28
标题:Carnosic acid derivatives for promoting synthesis of nerve growth factor
发明人：KOSAKA KUNIO; MIYAZAKI TOSHITSUGU; YOKOI TOSHIO
权利人:NAGASE & CO LTD
摘要:A novel carnosic acid derivative for promoting the synthesis of nerve growth factor (NGF), a composition comprising the carnosic acid derivative as an effective ingredient, as well as, a method of promoting the synthesis of NGF comprising administering an effective amount of the carnosic acid derivative as an effective ingredient to a subject requiring such promotion. The carnosic acid derivative, composition and method according to the present invention can safely and efficiently promote the production of NGF in the living body, without being accompanied by a side effect such as a loss of a quantitative balance of hormones in the living body.

专利号:US-5139940-A
优先权日:1989-10-26
标题 :Activation compounds and methods of synthesis of activation compounds
发明人：ISAACS STEPHEN T; CIMINO GEORGE D; METCHETTE KENNETH C; TESSMAN JOHN W
权利人:ISAACS STEPHEN T; CIMINO GOERGE D; METCHETTE KENNETH C; TESSMAN JOHN W
摘要:The invention is directed to isopsoralen compound compositions that contain a variety of substitutions which yet permit their binding to nucleic acid polymers. Reaction conditions that activate these bound isopsoralens results in covalent crosslinking to the nucleic acid polymers. The resultant complex is inhibited from being a template for the template-directed enzymatic synthesis of a complementary nucleic acid polymer. Beside the isopsoralens compositions, the invention includes their synthesis, the nucleic acid complex production and detection, and the above inhibitory method of use of the isopsoralens.

专利号:US-5247099-A
优先权日:1989-08-17
标题:Process for synthesis of 7-hydroxy coumarins having substitutions in the 4-position
发明人：CELEBUSKI JOSEPH E
权利人:ABBOTT LAB
摘要:A process for synthesis of a compound of the formula: said process comprising the steps of (a) reacting 4-bromomethyl-7-methoxy coumarin with a malonic ester under conditions sufficient to achieve condensation of the ester to give the monoalkylated (2-bis(carbalkoxy)-2-R1-1-ethyl) derivative; (b) removing one of the carbalkoxy groups from the product of step (a); (c) demethylation of the product of step (b) to give the 7-hydroxycoumarin compound; and (d) chemically modifying the remaining ester to yield a desired R2.

专利号:US-7888337-B2
优先权日:2007-08-31
标题 :Synthesis of oseltamivir containing phosphonate congeners with anti-influenza activity
发明人：WONG CHI-HUEY; FANG JIM-MIN; SHIE JIUN-JIE; CHENG YIH-SHYUN EDMOND; JAN JIA-TSRONG
权利人:ACADEMIA SINICA
摘要:Novel phosphonate compounds are described. The compounds have activity as neuraminidase inhibitors against wild-type and H274Y mutant of H1N1 and H5N1 viruses. The present disclosure also provides an enantioselective synthetic route to known neuraminidase inhibitors oseltamivir and the anti-flu drug TamifluÂ®, as well as novel phosphonate compounds, via D-xylose. Another efficient and flexible synthesis of Tamiflu and the highly potent neuraminidase inhibitor Tamiphosphor was also achieved in 11 steps and >20% overall yields from the readily available fermentation product (1S-cis)-3-bromo-3,5 -cyclohexadiene-1,2-diol. Most of the reaction intermediates were obtained as crystals without tedious purification procedures. The key transformations include an initial regio- and stereoselective bromoamidation of a bromoarene cis-dihydrodiol, as well as the final palladium-catalyzed carbonylation and phosphonylation.

专利号:US-6391344-B2
优先权日:1999-12-02
标题:Method of promoting synthesis of nerve growth factor
发明人：KOSAKA KUNIO; MIYAZAKI TOSHITSUGU; ITO HISATOMI
权利人:NAGASE & CO LTD
摘要:A method of promoting the synthesis of nerve growth factor comprising administering an effective amount of rosemary and/or sage extracts or carnosic acid and/or carnosol as an effective ingredient to a subject requiring such promotion. The present method can safely and efficiently promote the production of NGF in the living body, without being accompanied by a side effect such as a loss of a quantitative balance of hormones in the living body.

专利号:US-2014228554-A1
优先权日:2011-03-18
标题:Synthesis of new fucose-containing carbohydrate derivatives
发明人：CHAMPION ELISE; DEKANY GYULA; HEDEROS MARKUS; AGOSTON KAROLY
权利人:GLYCOM AS; GLYCOM AS
摘要:A method for the synthesis of a fucooligosaccharide glycosides by reacting a fucosyl donor with H-A-R 1 or a salt thereof, wherein A and R 1 are as defined herein, under the catalysis of an enzyme capable of transferring fucose is provided. The fucooligosaccharid glycoside compounds, or derivatives thereof, their use in the manufacture of human milk oligosaccharides, and a method of manufacture of human milk oligosaccharides, are also provided.

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主要参考文献

1: Zhu H, Ma X, Kong JY, Zhang M, Kenttämaa HI. Identification of Carboxylate, Phosphate, and Phenoxide Functionalities in Deprotonated Molecules Related to Drug Metabolites via Ion-Molecule Reactions with water and Diethylhydroxyborane. J Am Soc Mass Spectrom. 2017 Jul 24. doi: 10.1007/s13361-017-1713-0. [Epub ahead of print] doi: 10.1016/j.jchromb.2017.07.013. Epub 2017 Jul 10. pii: E600. doi: 10.3390/ijms18030600. Review.
4: Ouyang X, Panetta NJ, Talbott MD, Payumo AY, Halluin C, Longaker MT, Chen JK. Hyaluronic acid synthesis is required for zebrafish tail fin regeneration. PLoS One. 2017 Feb 16;12(2):e0171898. doi: 10.1371/journal.pone.0171898. eCollection 2017.
5: Shinomiya K, Zaima K, Harada Y, Yasue M, Harikai N, Tokura K, Ito Y. Comparison of the peak resolution and the stationary phase retention between the satellite and the planetary motions using the coil satellite centrifuge with counter-current chromatographic separation of 4-methylumbelliferyl sugar derivatives. J Chromatogr A. 2017 Jan 20;1481:64-72. doi: 10.1016/j.chroma.2016.12.027. Epub 2016 Dec 21.

合成参考文献

参考文献:10.1186/1472-6750-11-74
摘要:Mann DG, King ZR, Liu W, Joyce BL, Percifield RJ, Hawkins JS, LaFayette PR, Artelt BJ, Burris JN, Mazarei M, Bennetzen JL, Parrott WA, Stewart CN. Switchgrass (Panicum virgatum L.) polyubiquitin gene (PvUbi1 and PvUbi2) promoters for use in plant transformation. BMC Biotechnol. 2011 Jul 11;11():74.
参考文献:10.1007/s10930-011-9339-8
摘要:Calderon C, Abuin E, Lissi E, Montecinos R. Effect of human serum albumin on the kinetics of 4-methylumbelliferyl-β-D-N-N'-N″ Triacetylchitotrioside hydrolysis catalyzed by hen egg white lysozyme. Protein J. 2011 Aug;30(6):367–73. doi: 10.1007/s10930-011-9339-8.
参考文献:10.1007/s11418-011-0563-5
摘要:Kashiwada Y, Ahmed FA, Kurimoto S, Kim S, Shibata H, Fujioka T, Takaishi Y. New α-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam. Journal of Natural Medicines. 2011 Jul 05;66(1):217–21. doi: 10.1007/s11418-011-0563-5.
参考文献:10.1002/mus.20473
摘要:Slonim AE, Bulone L, Minikes J, Hays AP, Shanske S, Tsujino S, DiMauro S. Benign course of glycogen storage disease type IIb in two brothers: nature or nurture Muscle Nerve. 2006 Apr;33(4):571–4. doi: 10.1002/mus.20473.
参考文献:10.4061/2011/316939
摘要:Alquéres SMC, Branco RV, Freire DMG, Alves TLM, Martins OB, Almeida RV. Characterization of the Recombinant Thermostable Lipase (Pf2001) from Pyrococcus furiosus: Effects of Thioredoxin Fusion Tag and Triton X-100. Enzyme Research. 2011 Jun 30;2011():1–7. doi: 10.4061/2011/316939.