勒胖停 | 155-58-8

• 物质功能分类: 生物化工 - 中草药成分
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 勒胖停
• 中文别名: 土大黄苷；大黄素荧光指示剂；土大黄素.食用大黄素
• 英文名称: rhaponticin
• 英文别名: 3,3',5-trihydroxy-4'-methoxystilbene 3-O-β-D-glucoside；rhapontigenin-3-O-glucoside；rhapontin；UNPD24149；4'-methoxy-3,3',5-stilbenetriol 3-glucoside；(2S,3R,4S,5S,6R)-2-[3-hydroxy-5-[(E)-2-(3-hydroxy-4-methoxyphenyl)ethenyl]phenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 155-58-8
• 化学式: C₂₁H₂₄O₉
• 分子量: 420.416
• InChiKey: GKAJCVFOJGXVIA-DXKBKAGUSA-N

物化性质

• 熔点：
  236-240 °C
• 比旋光度：
  D32 -59.5° (acetone)
• 沸点：
  457.61°C (rough estimate)
• 密度：
  1.2828 (rough estimate)
• 溶解度：
  可溶于丙酮（少许）、DMSO（少许）、甲醇（少许）
• LogP：
  0.680 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  149
• 氢给体数：
  6
• 氢受体数：
  9

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S24/25
• 危险类别码：
  R36/38
• WGK Germany：
  3
• 海关编码：
  29389090
• 储存条件：
  请将密封保存。保存为Markdown格式。

SDS

Name:	Rhapontin, 95% Material Safety Data Sheet
Synonym:	4'Methoxy-3,3',5-stilbenetriol-3-glucoside
CAS:	155-58-8

Section 1 - Chemical Product MSDS Name: Rhapontin, 95% Material Safety Data Sheet
Synonym: 4'Methoxy-3,3',5-stilbenetriol-3-glucoside

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SECTION 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
155-58-8	Rhapontin	95%	205-845-0

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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SECTION 3 - HAZARDS IDENTIFICATION EMERGENCY OVERVIEW The toxicological properties of this material have not been fully investigated. Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
None

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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.
Skin:
Get medical aid if irritation develops or persists. Flush skin with plenty of soap and water.
Ingestion:
If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
Remove from exposure and move to fresh air immediately. Get medical aid if cough or other symptoms appear.
Notes to Physician:

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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.

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SECTION 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions.

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SECTION 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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SECTION 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low. Exposure Limits CAS# 155-58-8: 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.

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SECTION 9 - PHYSICAL AND CHEMICAL PROPERTIES
Physical State: Solid
Color: light yellow
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 236-238 deg C dec
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C21H24O9
Molecular Weight: 420.42

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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:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Will not occur.

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SECTION 11 - TOXICOLOGICAL INFORMATION RTECS#: CAS# 155-58-8 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
Rhapontin - Not listed by ACGIH, IARC, or NTP.

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SECTION 12 - ECOLOGICAL INFORMATION

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SECTION 13 - DISPOSAL CONSIDERATIONS Dispose of in a manner consistent with federal, state, and local regulations.

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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.

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SECTION 15 - REGULATORY INFORMATION European/International Regulations European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases: S 24/25 Avoid contact with skin and eyes. WGK (Water Danger/Protection) CAS# 155-58-8: No information available. Canada None of the chemicals in this product are listed on the DSL/NDSL list. CAS# 155-58-8 is not listed on Canada's Ingredient Disclosure List. US FEDERAL TSCA CAS# 155-58-8 is not listed on the TSCA inventory. It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
MSDS Creation Date: 9/02/1997 Revision #2 Date: 3/18/2003 The information above is believed to be accurate and represents the best information currently available to us. However, we make no warranty of merchantability or any other warranty, express or implied, with respect to such information, and we assume no liability resulting from its use. Users should make their own investigations to determine the suitability of the information for their particular purposes. In no way shall the company be liable for any claims, losses, or damages of any third party or for lost profits or any special, indirect, incidental, consequential or exemplary damages, howsoever arising, even if the company has been advised of the possibility of such damages.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

勒胖停是一种来源于土大黄的活性成分，具有多种生物活性和潜在应用。以下是对勒胖停的主要特性和应用的研究概述：

化学性质

• 溶解性：溶于甲醇、DMSO。

来源

• 勒胖停主要源自土大黄（Rheum palmatum）等中药植物。

生物活性与用途

1. 药理作用

   • 抗炎作用：勒胖停及其衍生物具有显著的抗炎效果，优于阿司匹林。
   • 抗过敏作用：在肠道菌群作用下转化为8-O-β-D-葡萄糖衍生物后表现出较好的抑制肥大细胞和过敏反应的效果。
   • 美白功能：通过抑制黑色素生成而发挥美白作用，并与勒胖停的浓度呈正相关。
   • 舒血管作用：可使收缩的大鼠胸大动脉放松，EC50值为5.8 µg/mL。
   • 抗肿瘤活性：体外对多种人癌细胞株有抑制作用。
   • 解酒功能：通过减少乙醇代谢成醛来减轻宿醉症状。
   • 雌激素样作用：具有微弱的雌激素效应，可应用于避孕药等产品的开发。

2. 神经保护与抗氧化

   • 对β淀粉样蛋白1-42有抵抗作用，有助于维持细胞生存能力和线粒体健康，可能用于阿尔茨海默病的治疗。

3. 其他应用：

   • 可作为抗过敏药物前药进行开发；
   • 抑制细胞凋亡。

研究进展

• 郭明等人探讨了勒胖停与人血清白蛋白结合反应机制，揭示其在体内分布和代谢行为。
• 徐颖等总结了勒胖停的研究现状和发展趋势，指出其广泛的应用前景。
• 沈于兰改进了对大黄中勒胖停的检测方法，提高了研究效率。

使用范围

• 作为中药成分进行含量测定；
• 药理实验中的鉴定与评估；
• 美白产品的开发基础材料。

综上所述，勒胖停作为一种多功能活性物质，在现代医药、美容等领域展现出巨大潜力。未来的研究将进一步明确其作用机制，并探索更多潜在用途。

反应信息

• 作为反应物：
  描述：

  勒胖停 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 9.0h， 以40 mg的产率得到丹叶大黄素
  参考文献：
  名称：

  Stilbene glycosides from Guibourtia tessmannii

  摘要：

  从Guibourtia tessmannii植物的茎 Bark中分离获得了顺式3,4-二甲氧基5-核糖糖基间苯二酚、拉普托因和匹死。

  DOI：

  10.1016/0031-9422(94)00915-g
• 作为产物：
  描述：

  3,5-二甲氧基碘苯 在 三乙醇胺 、 palladium diacetate 、 三溴化硼 、 silver carbonate 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 24.0h， 生成 勒胖停
  参考文献：
  名称：

  A Short Synthesis of Rhaponticin and its 3”-Fluoroanalog via a Wittig/Heck-Mizoroki Route

  摘要：

  胡薄荷次苷及其3”-氟类似物已从易得的起始原料中制备得到。这些合成中的关键步骤是使用碳酸银介导的糖苷化反应，用于选择性地形成β-糖苷键。在三乙醇胺中通过钯醋酸盐催化的Heck-Mizoroki反应，在同时去保护糖类的情况下，建立了芪类化合物的(E)构型。

  DOI：

  10.1515/znb-2011-0314

文献信息

• 31P-N.m.r. spectroscopy in wood chemistry. Phosphite derivatives of carbohydrates
  作者：Yuri Archipov、Dimitris S. Argyropoulos、Henry Bolker、Cyril Heitner

  DOI：10.1016/0008-6215(91)80005-8

  日期：1991.11

  and model compounds for lignin-carbohydrate complexes were reacted with 1,3,2-dioxaphospholanyl chloride, and the 31P-n.m.r. spectra of the derivatives were obtained in order to correlate the signals with the structural details of the compounds. The derivatives of most of the carbohydrates exhibited spectra containing well resolved signals in the range 138-132 p.p.m., and the number of lines accorded

  摘要使选定的无环和环状多元醇，单糖，二糖，高级寡糖和木质素-碳水化合物配合物的模型化合物与1,3,2-二氧杂磷酰氯酰氯反应，得到衍生物的31P-nmr光谱以使它们相互关联。表示化合物的结构细节。大多数碳水化合物的衍生物显示出的光谱包含在138-132 ppm范围内的分辨良好的信号，并且谱线数与相应化合物中的羟基数相符。单糖衍生物中C-1处磷原子的化学位移值是所涉及的端基异构体的特征。由于完全分解的光谱分别具有糖和木质素相关部分的特征信号，获得了相关模型化合物的一部分，该方法似乎非常适合于对木质素-碳水化合物复合物衍生的分子进行结构解析。对环糊精（环麦芽六-，庚-和八糖）进行了衍生化处理，检查后得出的光谱彼此之间存在显着差异。
• Antioxidant constituents from rhubarb: structural requirements of stilbenes for the activity and structures of two new anthraquinone glucosides
  作者：Hisashi Matsuda、Toshio Morikawa、Iwao Toguchida、Ji-Young Park、Shoichi Harima、Masayuki Yoshikawa

  DOI：10.1016/s0968-0896(00)00215-7

  日期：2001.1

  extracts from five kinds of rhubarb were found to show scavenging activity for DPPH radical and .O2-. Two new anthraquinone glucosides were isolated from the rhizome of Rheum undulatum L. together with two anthraquinone glucosides, a naphthalene glucoside, and 10 stilbenes. In the screening test for radical scavenging activity of rhubarb constituents, stilbenes and a naphthalene glucoside showed activity

  发现从5种大黄中提取的甲醇对DPPH自由基和.O2-具有清除活性。从大黄（Rheum undulatum L.）的根茎中分离出两个新的蒽醌葡糖苷，以及两个蒽醌葡糖苷，萘葡糖苷和10个对苯二酚。在对大黄成分的自由基清除活性的筛选试验中，丁苯二酚和萘葡萄糖苷具有活性，而蒽醌和番石榴苷则没有活性。此外，大多数对苯二酚通过叔丁基氢过氧化物抑制红细胞膜的脂质过氧化。对各种相关化合物的清除作用的详细研究表明以下结构要求；1）酚羟基对显示活性至关重要；2）没食子酰基部分增强活性；3）葡糖苷部分降低活性；4）二氢二苯乙烯衍生物保持对DPPH自由基的清除活性，但它们对.O2-的活性较弱。另外，具有3-羟基和4'-甲氧基的几个对苯二酚抑制黄嘌呤氧化酶。
• USE OF HYDROXYSTILBENES FOR DYEING, READY-TO-USE COMPOSITION CONTAINING THEM AND DYEING PROCESS
  申请人：——

  公开号：US20020016998A1

  公开（公告）日：2002-02-14

  The invention relates to the use of hydroxystilbenes for dyeing, to ready-to-use dye compositions comprising them, to a dyeing process using them and to a multi-compartment device containing the compositions used in the processes of the invention.

  这项发明涉及使用羟基芪醌染色，涉及包含它们的即用染料组合物，涉及使用它们的染色过程，以及包含用于该发明过程中使用的组合物的多室装置。
• USE OF SARMENTINE AND ITS ANALOGS FOR CONTROLLING PLANT PESTS
  申请人：Huang Huazhang

  公开号：US20110021358A1

  公开（公告）日：2011-01-27

  Methods and compositions for controlling plant pests, particularly weeds and/or plant phytopathogens using sarmentine and/or analogs thereof are disclosed.

  揭示了利用沙曼汀和/或其类似物控制植物害虫，特别是杂草和/或植物病原体的方法和组合物。
• [EN] STREPTOCOCCUS MUTANS GLUCOSYL TRANSFERASE INHIBITORS FOR DENTAL CARIES THERAPY<br/>[FR] INHIBITEURS DE GLUCOSYLE TRANSFÉRASE DE STREPTOCOCCUS MUTANS POUR LA THÉRAPIE DES CARIES DENTAIRES
  申请人：UAB RESEARCH FOUNDATION

  公开号：WO2019195430A1

  公开（公告）日：2019-10-10

  The present invention is related to the inhibition of the formation of Streptococci biofilms through the inhibition of glucosyl transferase (Gtf). Compounds, compositions and methods for inhibiting Streptococcus biofilm formation, as well as for preventing, inhibiting and/or treating the formation of dental caries, and methods of identifying compounds that prevent, inhibit and/or treat the formation of dental caries are provided.

  本发明涉及通过抑制葡萄糖基转移酶(Gtf)来抑制链球菌生物膜形成的方法。提供了用于抑制链球菌生物膜形成的化合物、组合物和方法，以及用于预防、抑制和/或治疗龋齿形成的方法，以及用于识别能够预防、抑制和/或治疗龋齿形成的化合物的方法。

表征谱图