5-羧基四甲基罗丹明

CAS: 91809-66-4 货号: C272928 分子式: C25H22N2O5 分子量: 430.45 EC号: 989-222-5
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级别和纯度: ≥97%
储存条件
避光,-20°C储存,干燥
运输条件
超低温运输
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库存
价格
数量
50mg
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为什么选择此级别

提供 ≥97% 纯度,适用于对基线干扰要求严格的色谱和分析工作流程。

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文献证明

在色谱分析、有机合成和交叉偶联反应领域已被 3 篇同行评审文献引用。

概述

Fluorescent Dye Carboxylic Acids and Their Succinimidyl Esters

Succinimidyl esters are proven to be the best reagents for amine modifications because the amide bonds that are formed are essentially identical to, and as stable as the natural peptide bonds. These reagents are generally stable and show good reactivity and selectivity with aliphatic amines.  There are few factors that need be considered when SE compounds are used for conjugation reaction: 

1). Solvents:For the most part, reactive dyes are hydrophobic molecules and should be dissolved in anhydrous dimethylformamide (DMF) or dimethylsulfoxide (DMSO). 

2). Reaction pH:The labeling reactions of amines with succinimidyl esters are strongly pH dependent. Amine-reactive reagents react with non-protonated aliphatic amine groups, including the terminal amines of proteins and the e-amino groups of lysines. Thus amine acylation reactions are usually carried out above pH 7.5. Protein modifications by succinimidyl esters can typically be done at pH 7.5-8.5, whereas isothiocyanates may require a pH 9.0-10.0 for optimal conjugations. 

3).Reaction Buffers:Buffers that contain free amines such as Tris and glycine and thiol compounds must be avoided when using an amine-reactive reagent. Ammonium salts (such as ammonium sulfate and ammonium acetate) that are widely used for protein precipitation must also be removed (such as viadinlysis) before performing dye conjugations. 

4). Reaction Temperature:Most conjugations are done at room temperature. However, either elevated or reduced temperature may be required for a particular labeling reaction.

Features and Biological Applications

5-TAMRA is the purified single isomer of 5(6)-TAMRA. It is widely used to label peptides and proteins. It is preferred for some complicated biological applications where reproducibility is more critical than material cost since the minor positional difference between 5-TAMRA and 6-TAMRA might affect some biological properties of the underlying conjugates.

Product parameter

Ex(nm):541

Em(nm):568

References

1. Evans NA, et al. (2001). Visualizing differences in ligand-induced beta-arrestin-GFP interactions and trafficking between three recently characterized G protein-coupled receptors. J Neurochem77, 476-85.

2. Hahn, M., et al., Influence of fluorophor dye labels on the migration behavior of polymerase chain reaction—amplified short tandem repeats during denaturing capillary electrophoresis.Electrophoresis2001, 22, 2691-700.

3. Yoo H and Juliano RL (2000). Enhanced delivery of antisense oligonucleotides with fluorophore- conjugated PAMAM dendrimers. Nucleic Acids Res28, 4225-31. 

Fluorescent Dye Carboxylic Acids and Their Succinimidyl Esters

Succinimidyl esters are proven to be the best reagents for amine modifications because the amide bonds that are formed are essentially identical to, and as stable as the natural peptide bonds. These reagents are generally stable and show good reactivity and selectivity with aliphatic amines.  There are few factors that need be considered when SE compounds are used for conjugation reaction: 

1). Solvents:For the most part, reactive dyes are hydrophobic molecules and should be dissolved in anhydrous dimethylformamide (DMF) or dimethylsulfoxide (DMSO). 

2). Reaction pH:The labeling reactions of amines with succinimidyl esters are strongly pH dependent. Amine-reactive reagents react with non-protonated aliphatic amine groups, including the terminal amines of proteins and the e-amino groups of lysines. Thus amine acylation reactions are usually carried out above pH 7.5. Protein modifications by succinimidyl esters can typically be done at pH 7.5-8.5, whereas isothiocyanates may require a pH 9.0-10.0 for optimal conjugations. 

3).Reaction Buffers:Buffers that contain free amines such as Tris and glycine and thiol compounds must be avoided when using an amine-reactive reagent. Ammonium salts (such as ammonium sulfate and ammonium acetate) that are widely used for protein precipitation must also be removed (such as viadinlysis) before performing dye conjugations. 

4). Reaction Temperature:Most conjugations are done at room temperature. However, either elevated or reduced temperature may be required for a particular labeling reaction.

Features and Biological Applications

5-TAMRA is the purified single isomer of 5(6)-TAMRA. It is widely used to label peptides and proteins. It is preferred for some complicated biological applications where reproducibility is more critical than material cost since the minor positional difference between 5-TAMRA and 6-TAMRA might affect some biological properties of the underlying conjugates.

Product parameter

Ex(nm):541

Em(nm):568

References

1. Evans NA, et al. (2001). Visualizing differences in ligand-induced beta-arrestin-GFP interactions and trafficking between three recently characterized G protein-coupled receptors. J Neurochem77, 476-85.

2. Hahn, M., et al., Influence of fluorophor dye labels on the migration behavior of polymerase chain reaction—amplified short tandem repeats during denaturing capillary electrophoresis.Electrophoresis2001, 22, 2691-700.

3. Yoo H and Juliano RL (2000). Enhanced delivery of antisense oligonucleotides with fluorophore- conjugated PAMAM dendrimers. Nucleic Acids Res28, 4225-31. 

规格

英文别名
2-[3,6-bis(dimethylamino)xanthenium-9-yl]-5-carboxybenzoate | 2-(3,6-Bis(dimethylamino)xanthylium-9-yl)-5-carboxybenzoate | 5(6)-TAMRA Acid | BCP20413 | AKOS032949753 | BP-23469 | 5-Carboxytetramethyl Rhodamine | AKOS016000326 | DTXSID20376330 | F12248 |
规格或纯度
≥97%
英文名称
5-TAMRA
储存条件
避光,-20°C储存,干燥
运输条件
超低温运输
纯度
≥97%
名称和识别符
PubChem SID
分子类型
小分子
IUPAC Name
3-carboxy-4-[3-(dimethylamino)-6-dimethylazaniumylidenexanthen-9-yl]benzoate
INCHI
1S/C25H22N2O5/c1-26(2)15-6-9-18-21(12-15)32-22-13-16(27(3)4)7-10-19(22)23(18)17-8-5-14(24(28)29)11-20(17)25(30)31/h5-13H,1-4H3,(H-,28,29,30,31)
InChi Key
YMZMTOFQCVHHFB-UHFFFAOYSA-N
Smiles
CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=C(C=C(C=C4)C(=O)[O-])C(=O)O
Isomeric SMILES
CN(C)C1=CC2=C(C=C1)C(=C3C=CC(=[N+](C)C)C=C3O2)C4=C(C=C(C=C4)C(=O)[O-])C(=O)O
分子量
430.45
Reaxy-Rn
27597948
Reaxys-RN link address
https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=27597948&ln=

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高级数据

系统学分类

分类树(Taxonomy Tree)

界(kingdom) 有机化合物
超类(Superclass) 有机杂环化合物
类(Class) 苯并吡喃类
亚类(Subclass) 1-苯并吡喃
中间层级节点(Intermediate Tree Nodes) 二苯并吡喃
直接上位类(Direct Parent) 黄酮类
其他上位类(Alternative Parents) 间苯二甲酸及其衍生物  苯甲酸  苯甲酰衍生物  二烷基芳胺  二羧酸及其衍生物  二级酮亚胺  杂芳族化合物  氨基酸  羧酸盐  氧环化合物  羧酸  碳氢化合物衍生物  有机氧化物  有机盐  有机两性离子  有机氧化合物  有机光子化合物  
分子骨架(Molecular Framework) 芳香族杂多环化合物
取代基(Substituents) 氨基酸 - 氨基酸 - 氨基酸或其衍生物 - 芳香族杂多环化合物 - 苯基化合物 - 苯甲酸 - 苯甲酸或衍生物 - 苯甲酰 - 羧酰胺基 - 羧酸衍生物 - 羧酸盐 - 二烷基芳基胺 - 二羧酸或其衍生物 - 杂芳香族化合物 - 烃衍生物 - 间苯二甲酸 - 单环苯基基团 - 有机硝基化合物 - 有机氧化物 - 有机氧化合物 - 有机盐 - 有机双性离子 - 有机氮化合物 - 有机氧化合物 - 有机氮化合物 - 氧杂环 - 醛酮亚胺 - 三级脂肪族/芳香族胺 - 三芳基胺 - 黄蒽
描述(Description) 该化合物属于有机化合物中的呋喃类。这类多环芳烃化合物含有呋喃结构单元,由两个苯环通过吡喃环相互连接而成。
外部描述符(External Descriptors) xanthenes
三维结构
交互式化学结构模型





化学和物理性质
敏感性
对光和湿度敏感
闪点(℉)
92.5 °C
闪点(℃)
92.5°C
分子量
430.500 g/mol
XLogP3
3.200
氢键供体数Hydrogen Bond Donor Count
1
氢键受体数Hydrogen Bond Acceptor Count
6
可旋转键计数Rotatable Bond Count
3
精确质量Exact Mass
430.153 Da
单同位素质量Monoisotopic Mass
430.153 Da
拓扑极表面积Topological Polar Surface Area
92.900 Ų
重原子数Heavy Atom Count
32
形式电荷Formal Charge
0
复杂度Complexity
875.000
同位素原子数Isotope Atom Count
0
定义的原子立体中心计数Defined Atom Stereocenter Count
0
未定义的原子立体中心计数Undefined Atom Stereocenter Count
0
定义的键立体中心计数Defined Bond Stereocenter Count
0
未定义的键立体中心计数Undefined Bond Stereocenter Count
0
所有立体化学键的总数The total count of all stereochemical bonds
0
共价键合单元计数Covalently-Bonded Unit Count
1
安全和危险性(GHS)
WGK Germany
3
个人防护装备
Eyeshields,Gloves,type N95 (US),type P1 (EN143) respirator filter
质检证书(CoA,COO,BSE/TSE 和分析图谱)
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找到11个结果

批号(Lot Number) 证书类型 货号
J2307056 分析证书 C272928
I2602028 分析证书 C272928
C2208267 分析证书 C272928
C2208268 分析证书 C272928
L2403237 分析证书 C272928
J2114486 分析证书 C272928
F2518147 分析证书 C272928
F2505032 分析证书 C272928
B2306914 分析证书 C272928
J2114459 分析证书 C272928
J2114476 分析证书 C272928
技术文档和文章
此产品的引用文献
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常见问题

本产品的纯度是多少?
本产品的化学纯度(含量)为 ≥97%。批次的具体数值以分析证书(COA)为准。
本产品应如何储存?
请于?20 °C、避光、干燥条件下保存。请与干燥剂一同密封保存,本品对湿气敏感。
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本产品的 CAS 号、分子式和分子量是多少?
本产品的 CAS 号为 91809-66-4,分子式为 C25H22N2O5,分子量为 430.45 g/mol。InChIKey YMZMTOFQCVHHFB-UHFFFAOYSA-N。
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