4-羟基-7-甲氧基香豆酯 | 17575-15-4

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 4-羟基-7-甲氧基香豆酯
• 中文别名: 4-羟基-7-甲氧基香豆素
• 英文名称: 4-hydroxy-7-methoxycoumarine
• 英文别名: 4-hydroxy-7-methoxycoumarin；4-hydroxy-7-methoxy-2H-chromen-2-one；7-methoxy-4-hydroxycoumarin；4-Hydroxy-7-methoxycumarin；4-hydroxy-7-methoxy-2H-1-benzopyran-2-one；4-hydroxy-7-methoxy-2H-benzopyran-2-one；4-hydroxy-7-methoxychromen-2-one
• CAS: 17575-15-4
• 化学式: C₁₀H₈O₄
• mdl: MFCD00673700
• 分子量: 192.171
• InChiKey: MJBHLQMPKBMZSF-UHFFFAOYSA-N

物化性质

• 熔点：
  263-265 °C
• 沸点：
  248.14°C (rough estimate)
• 密度：
  1.0825 (rough estimate)
• 溶解度：
  可溶于丙酮、二甲基亚砜
• 最大波长(λmax)：
  308nm(EtOH)(lit.)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

ADMET

代谢

4-羟基-7-甲氧基香豆素是7-甲氧基香豆素的人类已知代谢物。

4-Hydroxy-7-methoxycoumarin is a known human metabolite of 7-methoxycoumarin.

来源:NORMAN Suspect List Exchange

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2932209090
• 危险类别：
  IRRITANT
• 安全说明：
  S26,S37/39
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  室温且干燥环境下使用。

SDS

Name:	4-Hydroxy-7-Methoxycoumarin Material Safety Data Sheet
Synonym:	None
CAS:	17575-15-4

Section 1 - Chemical Product MSDS Name:4-Hydroxy-7-Methoxycoumarin Material Safety Data Sheet
Synonym:None

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
17575-15-4	4-Hydroxy-7-Methoxycoumarin	100	unlisted

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. The toxicological properties of this material have not been fully investigated.
Skin:
May cause skin irritation. The toxicological properties of this material have not been fully investigated.
Ingestion:
May cause gastrointestinal irritation with nausea, vomiting and diarrhea. 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:
No information found.

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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 immediately.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
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 immediately.
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.
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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Vapors may be heavier than air. They can spread along the ground and collect in low or confined areas.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up or absorb material, then place into a suitable clean, dry, closed container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation. 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# 17575-15-4: 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:
A NIOSH/MSHA approved or European Standard EN 149 air purifying respirator with an organic vapor cartridge or canister may be permissible under certain circumstances where airborne concentrations are expected.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: Not available.
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: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H8O4
Molecular Weight: 192.0536

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 17575-15-4 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
4-Hydroxy-7-Methoxycoumarin - 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
No information available.
IMO
No information available.
RID/ADR
No information available.

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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 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable 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# 17575-15-4: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 17575-15-4 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 17575-15-4 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  4-羟基-7-甲氧基香豆酯 在 磷酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 苯 为溶剂， 生成 8-methoxy-2,2-dimethyl-2H,5H-pyrano<3,2-c><1>benzopyran-5-one
  参考文献：
  名称：

  Ahluwalia, V. K.; Arora, K. K.; Mukherjee, Irani, Heterocycles, 1984, vol. 22, # 2, p. 223 - 227

  摘要：

  DOI：
• 作为产物：
  描述：

  丹皮酚 在 sodium hydride 、 barium(II) hydroxide 作用下， 以 甲醇 、 水 、 mineral oil 为溶剂， 反应 2.0h， 生成 4-羟基-7-甲氧基香豆酯
  参考文献：
  名称：

  Pd催化的二氢吡喃烯丙基烷基化级联反应：呋喃并[3,2- c ]吡喃的区域选择性合成

  摘要：

  区域选择性钯催化的烯丙基烷基化级联反应由各种环状β-二羰基双亲核试剂和3,6-二氢-2 H-吡喃双亲电试剂形成呋喃[3,2- c ]吡喃。二氢吡喃底物中的烯丙基碳酸酯和异头甲硅烷氧基离去基团的组合允许控制该反应中许多区域化学的可能性。环合进行立体会聚，以从顺式或反式取代的起始原料产生顺式融合的呋喃吡喃。

  DOI：

  10.1021/ol400902d

文献信息

• 4-芳香胺-香豆素衍生物及其制备方法和医药 用途
  申请人：中国药科大学

  公开号：CN105801543B

  公开（公告）日：2019-08-02

  本发明涉及药物化学领域，具体涉及一系列4‑芳香胺‑香豆素衍生物、其制备方法及医药用途，特别是用于治疗肿瘤方面的药物，如乳腺癌等。本发明中涉及化合物的结构通式如下，通式中各基团定义详见说明书。
• Design, Synthesis, and Evaluation of in Vitro and in Vivo Anticancer Activity of 4-Substituted Coumarins: A Novel Class of Potent Tubulin Polymerization Inhibitors
  作者：Dong Cao、Yibin Liu、Wei Yan、Chunyu Wang、Peng Bai、Taijin Wang、Minghai Tang、Xiaoyan Wang、Zhuang Yang、Buyun Ma、Liang Ma、Lei Lei、Fang Wang、Bixue Xu、Yuanyuan Zhou、Tao Yang、Lijuan Chen

  DOI：10.1021/acs.jmedchem.6b00158

  日期：2016.6.23

  activity toward a panel of tumor cell lines at subnanomolar IC50 values. Compound 65 showed potent antiproliferative ability (IC50 values of 7–47 nM) and retained full activity in multidrug resistant cancer cells. Compound 65 caused G2/M phase arrest and interacted with the colchicine-binding site in tubulin, as confirmed by immune-fluorescence staining, microtubule dynamics assays, and competition

  本文合成了一系列新型的4-取代香豆素衍生物。在这些化合物中34，39，40，43，62，65，和67朝向在亚纳摩尔IC的肿瘤细胞系显示出面板显著抗增殖活性50值。化合物65显示出有效的抗增殖能力（IC 50值为7–47 nM），并在多药耐药癌细胞中保留了全部活性。化合物65免疫荧光染色，微管动力学分析和N，N'-亚乙基双（碘乙酰胺）竞争分析证实，导致G2 / M期停滞并与微管蛋白中的秋水仙碱结合位点相互作用。化合物65减少了HUVEC细胞中的细胞迁移并破坏了毛细血管样管的形成。重要的是，化合物65在包括紫杉醇敏感性和耐药性卵巢肿瘤（A2780s和A2780 / T），金霉素敏感性和耐药性乳腺肿瘤（MCF-7和MCF-7 / ADR）的四个异种移植模型中显着且剂量依赖性地降低了肿瘤的生长，提示化合物65是一种有前途的新型抗有丝分裂化合物，可用于潜在的癌症治疗。
• Electrooxidative Metal‐Free Cyclization of 4‐Arylaminocoumarins with DMF as C1‐Source
  作者：Yiyi Weng、Hantao Chen、Nanhui Li、Long Yang、Lutz Ackermann

  DOI：10.1002/adsc.202100146

  日期：2021.6.8

  An environmentally-benign electrochemical approach for the construction of quinoline derivatives employing N,N-dimethylformamide (DMF) as the methine source has been devised by cyclization of 4-(phenylamino)-2H-chromen-2-ones. In a user-friendly undivided cell, 6H-chromeno[4,3-b]quinolin-6-ones were obtained under chemical oxidant-free and transition-metal-free conditions in 43–92% yields with high

  已经通过 4-(苯基氨基) -2H -chromen-2-ones的环化设计了一种环境友好的电化学方法，用于构建使用N，N-二甲基甲酰胺 (DMF) 作为次甲基源的喹啉衍生物。在用户友好的无隔膜电解槽，6H -chromeno [4,3- b ]喹啉-6-酮进行化学氧化剂-自由和过渡金属-自由条件下在具有高功能性公差43-92％的产率获得。
• A new route to substituted furocoumarins <i>via</i> copper-catalyzed cyclization between 4-hydroxycoumarins and ketoximes
  作者：Tuong A. To、Yen H. Vo、Anh T. Nguyen、Anh N. Q. Phan、Thanh Truong、Nam T. S. Phan

  DOI：10.1039/c8ob01064a

  日期：——

  A new route to substituted furocoumarins via copper-catalyzed cyclization between 4-hydroxycoumarins and ketoximes was developed. CuBr2 exhibited higher activity than other copper salts, affording the desired furocoumarins in high yields. The transformation proceeded readily in the absence of stoichiometric external oxidants. The significance of this synthetic strategy would be (1) the easily available

  开发了一种通过4-羟基香豆素和酮肟之间的铜催化环化反应取代呋喃香豆素的新途径。CuBr 2表现出比其他铜盐更高的活性，从而以高收率提供了所需的呋喃香豆素。在没有化学计量外部氧化剂的情况下，转化容易进行。这种综合策略的意义将是：（1）容易获得的起始材料；（2）低成本催化剂CuBr 2；（3）没有化学计量的外部氧化剂。该协议是取代呋喃香豆素合成中先前方法的补充。
• Development of Coumarin-Based Hydroxamates as Histone Deacetylase Inhibitors with Antitumor Activities
  作者：Na Zhao、Feifei Yang、Lina Han、Yuhua Qu、Di Ge、Hua Zhang

  DOI：10.3390/molecules25030717

  日期：——

  Histone deacetylases (HDACs) have been proved to be promising targets for the treatment of cancer, and five histone deacetylase inhibitors (HDACis) have been approved on the market for the treatment of different lymphomas. In our previous work, we designed a series of novel coumarin-containing hydroxamate HDACis, among which compounds 6 and 7 displayed promising activities against tumor growth. Based

  组蛋白脱乙酰酶（HDACs）已被证明是治疗癌症的有希望的靶点，五种组蛋白脱乙酰酶抑制剂（HDACis）已被批准上市，用于治疗不同的淋巴瘤。在我们之前的工作中，我们设计了一系列新型含香豆素异羟肟酸酯HDACis，其中化合物6和7表现出良好的抗肿瘤生长活性。基于分子对接研究，我们进一步开发了 26 种其他类似物，旨在提高设计化合物的活性。其中几种新衍生物不仅表现出优异的 HDAC1 抑制作用，而且对四种人类癌细胞系表现出显着的生长抑制活性。代表性化合物 13a 和 13c 对实体瘤细胞系表现出有效的抗增殖活性，IC50 值为 0.36–2.91 µM，对 Beas-2B 和 L-02 正常细胞具有低细胞毒性。免疫印迹分析显示，13a 和 13c 剂量依赖性地增加组蛋白 H3 和 H4 的乙酰化。重要的是，这两种化合物对 MDA-MB-231 细胞系表现出比 SAHA 更好的抗转移作用。此外，1