989-38-8

• 常用中文名：罗丹明6G
• 常用英文名：Rhodamine 6G
• CAS号：989-38-8
• 分子式：C₂₈H₃₁ClN₂O₃
• 分子量：479.010
• 相关类别： 染料及颜料 染料 碱性染料
• 发布时间：2018-02-07 08:00:00
• 更新时间：2024-01-02 16:44:10
• Rhodamine 6G是罗丹明类似物,可用于Pgp外排测定试验中。它可用于MRP1-介导外排的动力学试验中,以及作为激光染料和具有线粒体探针的潜力。

名称

• 中文名: 碱性红 1
• 英文名: rhodamine 6G
• 中文别名: 罗丹明6G; 碱性红1; 玫瑰红6G; 玫瑰精6G; 9-[2-(乙氧羰基)苯基]-3,6-二(乙氨基)-2,7-二甲基氯化占吨翁
• 英文别名: fanal pink gfk; Rhodamine 590 chloride; Rhodamine 5GDN; rhodamin6g; Aizen Rhodamine 6GCP; Basic rhodamine yellow; rh6g; rhodamine 4gh; calcozine red 6g; rhodamine 6gb; Rhodamine 6GDN Extra; Basic Rhodaminic Yellow; Rhodamine 6JH-SA Extra 1150; Mitsui Rhodamine 6GCP; cibasicred1; Rhodamine 6G Extra; Basonyl Red 483; CI Basic Red 1; Basonyl Red 482; Rhodamine 6GBN; Nyco Liquid Red GF; Basic red 1; Rhodamine 5GL; Ethyl 2-[(3Z)-6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xanthen-9-yl]benzoate hydrochloride (1:1); Rhodamine 6JH; Flexo Red 482; Rhodamine 5GDN Extra; Eljon Pink Toner; Rhodamine F 5GL; fanalpinkb; Rhodamine F 5G; Rhodamine GDN Extra; Rhodamine 6G Extra Base; Rhodamine 6GCP; Fanal Pink B; red169; Calcozine Rhodamine 6GX; rhodaminej; Heliostable Brilliant Pink B Extra; Vali Fast Red 1308; Rhodamine 6G; rhodamine 3B hydrochloride; MFCD00012665; ethyl 2-[(3Z)-6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xanthen-9-yl]benzoate hydrochloride; Benzoic acid, 2-[(3Z)-6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xanthen-9-yl]-, ethyl ester, hydrochloride (1:1); Rhodamine 6GD; rhodamine y 20-7425; Mitsui Rhodamine; N-[(3Z)-9-[2-(Ethoxycarbonyl)phenyl]-6-(ethylamino)-2,7-dimethyl-3H-xanthen-3-ylidene]ethanaminium chloride; Rhodamine 4GD; silosuper pink b; Rhodamine 6Zh-DN; benzoic acid, 2-[(3Z)-6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xanthen-9-yl]-, ethyl ester, monohydrochloride; Rhodamine 6GDN; Rh 6G; Elcozine Rhodamine 6GDN; Rhodamine 6GO; Rhodamine 6GH; rhodaminezh; rhodamine 6gex ethyl ester; EINECS 213-584-9; Fanal Red 25532; rhodamine gdn; rhodamine 6gx; Rhodamine 6G chloride; rhodamine ZH

物化性质

• 密度: 1.15g/cm3
• 沸点: <200ºC
• 熔点: 290 °C
• 分子式: C₂₈H₃₁ClN₂O₃
• 分子量: 479.010
• 闪点: 318.6ºC
• 精确质量: 478.202332
• PSA: 63.83000
• LogP: 7.22550
• 外观性状: 红色至棕色粉末
• 折射率: 1.593
• 储存条件:

  保持容器密封，储存在阴凉，干燥的地方

• 稳定性:

  常温常压下稳定，避免氧化物接触

• 水溶解性: SOLUBLE
• 分子结构:

  1、 摩尔折射率：130.20

  2、 摩尔体积（cm³/mol）：384.1

  3、 等张比容（90.2K）：962.1

  4、 表面张力（dyne/cm）：39.3

  5、 极化率（10^-24cm³）：51.61

• 计算化学:

  1、 氢键供体数量：2

  2、 氢键受体数量：5

  3、 可旋转化学键数量：7

  4、 拓扑分子极性表面积（TPSA）：59.9

  5、 重原子数量：34

  6、 表面电荷：0

  7、 复杂度：868

  8、 同位素原子数量：0

  9、 确定原子立构中心数量：0

  10、 不确定原子立构中心数量：0

  11、 确定化学键立构中心数量：0

  12、 不确定化学键立构中心数量：0

  13、 共价键单元数量：1

• 更多:

  1. 性状：红色或黄棕色粉末。对光敏感。

  2. 密度（g/mL,25/4℃）：未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：290℃

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,5.2kPa）：未确定

  7. 折射率：未确定

  8. 闪点（ºC）：未确定

  9. 比旋光度（º）：未确定

  10. 自燃点或引燃温度（ºC）：未确定

  11. 蒸气压（kPa,25ºC）：未确定

  12. 饱和蒸气压（kPa,60ºC）：未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）：未确定

  15. 临界压力（KPa）：未确定

  16. 油水（辛醇/水）分配系数的对数值：未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）：未确定

  19. 溶解性：溶于醇类呈橙红色荧光，溶于水呈猩红色显绿色荧光，在浓硫酸中呈黄色稀释变红，水溶液加入苛性钠生成红色沉淀。

生物活性

• 描述: Rhodamine 6G是罗丹明类似物,可用于Pgp外排测定试验中。它可用于MRP1-介导外排的动力学试验中,以及作为激光染料和具有线粒体探针的潜力。
• 相关类别:
  信号通路 >> 其他 >> 其他
  染料试剂
  研究领域 >> 其他
• 体外研究: 罗丹明6G,也称为罗丹明590,广泛用作激光介质和荧光示踪剂。用于染料激光,它溶于甲醇,乙醇和各种其他有机溶剂。在环境流量研究中,示踪介质通常是水。在乙醇中,罗丹明6G的吸收范围在440nm和570nm之间,峰值在530nm。因此,它非常适合于通过倍频Nd：YAG激光器在532nm处泵浦,铜蒸气激光器在511nm处泵浦,以及氩离子激光器在514nm处泵浦。得到的发射光谱在约510nm至约710nm之间变化,峰值在550nm处,取决于溶剂和染料浓度。然而,激光发射范围窄得多,从约560nm到610nm,峰值波长约为575nm。能够实现大于50％的能量转换效率。为了选择最佳溶剂和染料浓度,对其效果的充分了解是一个先决条件。 DMSO中的罗丹明6G显示出明显的行为,仅显示出具有11nm红移波长的甲醇情况的41％的荧光强度。对于不同的溶剂,观察到相对小的荧光光谱变化;观察到甲醇的最高荧光强度,DMSO的荧光强度最低。最短的峰值波长在甲醇(568nm)中发现,在DMSO(579nm)中最长。改变染料浓度可提供稀释情况下550 nm和高浓度620 nm之间的可调性,此时荧光光谱显示罗丹明6G聚集体的形成[1]。罗丹明6G是能够穿透活细胞的荧光染料。进入细胞后,罗丹明6G与线粒体的内膜结合。基于这些观察,已经提出罗丹明染料可以用于产生具有低背景噪声和高分辨率的线粒体的荧光图像。极低浓度的若丹明6G似乎可以选择性地破坏培养中的恶性细胞,从而节省正常细胞群[2]。
• 体内研究: 与未治疗的对应物相比,接受罗丹明6G的黑素瘤移植小鼠显示出延长的存活期,改善的临床参数,抑制肿瘤生长和转移计数。每周两次10-6M罗丹明6G方案产生最显着的结果[2]。罗丹明-6G进入循环系统并标记白细胞。通过确定滚动和粘附的白细胞的数量以及这些细胞的总通量,可以监测白细胞和内皮细胞之间相互作用的变化[3]。
• 细胞实验: 将恶性细胞和正常对照培养物以相等（蛋白质调节的）细胞量接种到6孔组织培养板中。用25μCi/ mL的3H-胸苷脉冲细胞，立即用固定浓度1μM的罗丹明6G处理24h，48h，72h或5天（120h）。在24小时，48小时，72小时或5天后，用PBS洗涤过量的放射性物质。将细胞样品转移到含有4ml闪烁液的聚苯乙烯小瓶中，并在β-计数器中计数它们的放射性。通过Bradford的试验评估总细胞蛋白[2]。
• 动物实验: 小鼠：C57B1小鼠植入B16-F10黑素瘤，并以不同剂量/时间方案用罗丹明6G（1,0.1,0.01μM）处理。分析培养的肿瘤细胞的活力和增殖[2]。
• 参考文献:

  [1]. Zehentbauer FM, et al. Fluorescence spectroscopy of Rhodamine 6G: concentration and solvent effects. Spectrochim Acta A Mol Biomol Spectrosc. 2014;121:147-51.

  [2]. Kutushov M, et al. Low concentrations of Rhodamine 6G selectively destroy tumor cells and improve survival of melanoma transplanted mice. Neoplasma. 2013;60(3):262-73.

  [3]. Jain RK, et al. Measuring leukocyte-endothelial interactions in mice. Cold Spring Harb Protoc. 2013 Jun 1;2013(6):561-3.

MSDS

Name: Rhodamine 6g Material Safety Data Sheet Synonym: Basic Red 1; C.I. 4516 CAS: 989-38-8 Section 1 - Chemical Product MSDS Name:Rhodamine 6g Material Safety Data Sheet Synonym:Basic Red 1; C.I. 4516 Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS CAS# Chemical Name content EINECS# 989-38-8 Rhodamine 6G ca. 100 213-584-9 Hazard Symbols: XN Risk Phrases: 40 Section 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW Limited evidence of a carcinogenic effect. Potential Health Effects Eye: May cause eye irritation. This product contains a cationic dye. Similar dyes have caused permanent injury to the cornea and conjunctiva in documented exposure cases with human or rabbit eyes. Skin: May cause skin irritation. Ingestion: May cause gastrointestinal irritation with nausea, vomiting and diarrhea. Inhalation: May cause respiratory tract irritation. Chronic: May cause cancer according to animal studies. Section 4 - FIRST AID MEASURES Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid immediately. Skin: Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Get medical aid if irritation develops or persists. Wash clothing before reuse. Ingestion: Never give anything by mouth to an unconscious person. Get medical aid. Wash mouth out with water. Inhalation: Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid if cough or other symptoms appear. Notes to Physician: Section 5 - FIRE FIGHTING MEASURES General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam. Section 6 - ACCIDENTAL RELEASE MEASURES General Information: Use proper personal protective equipment as indicated in Section 8. Spills/Leaks: Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions. Provide ventilation. Section 7 - HANDLING and STORAGE Handling: Wash thoroughly after handling. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Avoid contact with skin and eyes. Do not breathe dust, vapor, mist, or gas. Do not get in eyes, on skin, or on clothing. Keep container tightly closed. Use only in a chemical fume hood. Storage: Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION Engineering Controls: Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 989-38-8: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166. Skin: Wear appropriate protective gloves to prevent skin exposure. Clothing: Wear appropriate protective clothing to prevent skin exposure. Respirators: Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced. Section 9 - PHYSICAL AND CHEMICAL PROPERTIES Physical State: Solid Color: brown Odor: Not available. pH: Not available. Vapor Pressure: Not available. Viscosity: Not available. Boiling Point: Not available. Freezing/Melting Point: Not available. Autoignition Temperature: Not available. Flash Point: Not available. Explosion Limits, lower: Not available. Explosion Limits, upper: Not available. Decomposition Temperature: Solubility in water: soluble Specific Gravity/Density: Molecular Formula: C28H31ClN2O3 Molecular Weight: 479.01 Section 10 - STABILITY AND REACTIVITY Chemical Stability: Stable under normal temperatures and pressures. Conditions to Avoid: Incompatible materials. Incompatibilities with Other Materials: Strong oxidizing agents. Hazardous Decomposition Products: Hydrogen chloride, nitrogen oxides, carbon monoxide, carbon dioxide. Hazardous Polymerization: Will not occur. Section 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 989-38-8: DH0175000 LD50/LC50: Not available. Carcinogenicity: Rhodamine 6G - Not listed by ACGIH, IARC, or NTP. Other: See actual entry in RTECS for complete information. Section 12 - ECOLOGICAL INFORMATION Other No information available. Section 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations. Section 14 - TRANSPORT INFORMATION IATA Not regulated as a hazardous material. IMO Not regulated as a hazardous material. RID/ADR Not regulated as a hazardous material. Section 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives Hazard Symbols: XN Risk Phrases: R 40 Limited evidence of a carcinogenic effect. Safety Phrases: S 24/25 Avoid contact with skin and eyes. S 36/37 Wear suitable protective clothing and gloves. S 45 In case of accident or if you feel unwell, seek medical advice immediately (show the label where possible). WGK (Water Danger/Protection) CAS# 989-38-8: 2 Canada CAS# 989-38-8 is listed on Canada's DSL List. CAS# 989-38-8 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 989-38-8 is listed on the TSCA inventory. SECTION 16 - ADDITIONAL INFORMATION N/A

毒性和生态

毒理学数据: 有毒，最小致死量（小鼠，腹腔）2mg/kg. 生态学数据: 该物质对环境可能有危害，对水体应给予特别注意。 CHEMICAL IDENTIFICATION RTECS NUMBER : DH0175000 CHEMICAL NAME : Benzoic acid, o-(6-(ethylamino)-3-(ethylimino)-2,7-dimethyl-3H-xant hen-9-yl)-, ethyl ester, monohydrochloride CAS REGISTRY NUMBER : 989-38-8 LAST UPDATED : 199701 DATA ITEMS CITED : 27 MOLECULAR FORMULA : C28-H31-N2-O3.Cl MOLECULAR WEIGHT : 479.06 WISWESSER LINE NOTATION : T C666 BO EYJ EUN2 F1 IR BVO2& L1 MN1&1 &GH HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 125 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 50 mg/kg TOXIC EFFECTS : Cardiac - other changes Liver - other changes Blood - other hemolysis with or without anemia TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 6150 ug/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 2310 mg/kg/14D-C TOXIC EFFECTS : Related to Chronic Data - death TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 10192 mg/kg/13W-C TOXIC EFFECTS : Blood - changes in spleen TYPE OF TEST : TCLo - Lowest published toxic concentration ROUTE OF EXPOSURE : Inhalation SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 130 mg/kg/35D-I TOXIC EFFECTS : Lungs, Thorax, or Respiration - structural or functional change in trachea or bronchi Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 51 gm/kg/13W-C TOXIC EFFECTS : Nutritional and Gross Metabolic - weight loss or decreased weight gain TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 7725 mg/kg/2Y-C TOXIC EFFECTS : Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 100 mg/kg/1Y-I TOXIC EFFECTS : Tumorigenic - equivocal tumorigenic agent by RTECS criteria Tumorigenic - tumors at site of application TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 4 mg/kg SEX/DURATION : female 7-10 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - fetal death TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 2 mg/kg SEX/DURATION : female 7-10 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - other effects to embryo TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 2 mg/kg SEX/DURATION : female 7-10 day(s) after conception TOXIC EFFECTS : Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Intraperitoneal DOSE : 2 mg/kg SEX/DURATION : female 7-10 day(s) after conception TOXIC EFFECTS : Reproductive - Effects on Embryo or Fetus - other effects to embryo Reproductive - Specific Developmental Abnormalities - musculoskeletal system MUTATION DATA TYPE OF TEST : Sister chromatid exchange TEST SYSTEM : Rodent - hamster Ovary DOSE/DURATION : 19900 ug/L REFERENCE : NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-364,1989 *** REVIEWS *** IARC Cancer Review:Animal Limited Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 16,233,1978 IARC Cancer Review:Human No Adequate Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 16,233,1978 IARC Cancer Review:Group 3 IMSUDL IARC Monographs, Supplement. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) No.1- 1979- Volume(issue)/page/year: 7,56,1987 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - M2209 No. of Facilities: 917 (estimated) No. of Industries: 20 No. of Occupations: 21 No. of Employees: 15041 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - M2209 No. of Facilities: 2416 (estimated) No. of Industries: 27 No. of Occupations: 32 No. of Employees: 41538 (estimated) No. of Female Employees: 8238 (estimated)

安全

• 符号: GHS07
• 信号词: Warning
• 危害声明: H302
• 个人防护装备: dust mask type N95 (US);Eyeshields;Faceshields;Gloves
• 危害码 (欧洲): Xn:Harmful;
• 风险声明 (欧洲): R22
• 安全声明 (欧洲): S36/37/39-S26
• 危险品运输编码: NONH for all modes of transport
• WGK德国: 3
• RTECS号: DH0175000
• 海关编码: 3204130000

制备

1.3-乙氨基对甲苯酚 (p-cresol, 3-ethylamino) 和苯酐为原料，首先将两者缩合，然后再用乙醇进行酯化即得产物

2.以邻甲苯胺用氯乙烷烷基化，磺化，碱熔后与苯酐缩合，用氯乙烷酯化，经后处理得产品。

海关

海关编码	2922199090
中文概述	2922199090. 其他氨基醇及其醚，酯和它们的盐（但含一种以上含氧基的除外）. 增值税率:17.0%. 退税率:13.0%. 监管条件:无. 最惠国关税:6.5%. 普通关税:30.0%
申报要素	品名, 成分含量, 用途, 乙醇胺及其盐应报明色度, 乙醇胺及其盐应报明包装
Summary	2922199090. other amino-alcohols, other than those containing more than one kind of oxygen function, their ethers and esters; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%