5,7-二羟基-4-苯基香豆素 | 7758-73-8

• 物质功能分类: 催化剂及助剂 - 偶联剂
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 新黄酮类化合物
• 中文名称: 5,7-二羟基-4-苯基香豆素
• 中文别名: 57-二羟基-4-苯基香豆素；5,7-二羟基-4-苯基-2H-1-苯并吡喃-2-酮
• 英文名称: 5,7-dihydroxy-4-phenyl-2H-1-benzopyran-2-one
• 英文别名: 5,7-dihydroxy-4-phenylcoumarin；5,7-dihydroxy-4-phenyl-2H-chromen-2-one；5,7-dihydroxy-4-phenyl-chromen-2-one；DDE270；5,7-dihydroxy-4-phenylchromen-2-one
• CAS: 7758-73-8
• 化学式: C₁₅H₁₀O₄
• mdl: MFCD01078551
• 分子量: 254.242
• InChiKey: HUQKUJNSVHEHIH-UHFFFAOYSA-N

物化性质

• 熔点：
  227-233 °C (lit.)
• 沸点：
  535.5±19.0 °C(Predicted)
• 密度：
  1.443
• 溶解度：
  二甲基亚砜：250 mg/mL（983.32 mM）
• 稳定性/保质期：
  如果遵照规格使用和储存，则不会分解，未有已知危险发生。避免与强氧化剂接触。

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• 海关编码：
  2932209090
• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H315,H319,H335
• 储存条件：
  请将药品存放在密闭、阴凉干燥的地方，并保持良好通风。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product name : 5,7-Dihydroxy-4-phenylcoumarin

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
According to Regulation (EC) No1272/2008
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
According to European Directive 67/548/EEC as amended.
Irritating to eyes, respiratory system and skin.
Label elements
Pictogram
Signal word Warning
Hazard statement(s)
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/fume/gas/mist/vapours/spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Hazard symbol(s)
Xi Irritant
R-phrase(s)
R36/37/38 Irritating to eyes, respiratory system and skin.
S-phrase(s)
S26 In case of contact with eyes, rinse immediately with plenty of water and
seek medical advice.
S36 Wear suitable protective clothing.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Formula : C15H10O4
Molecular Weight : 254,24 g/mol
CAS-No. EC-No. Index-No. Classification Concentration
5,7-Dihydroxy-4-phenylcoumarin
7758-73-8 - - Skin Irrit. 2; Eye Irrit. 2; STOT -
SE 3; H315, H319, H335
Xi, R36/37/38
For the full text of the H-Statements mentioned in this Section, see Section 16.

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Section 4. FIRST AID MEASURES
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing give artificial respiration Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special protective equipment for fire-fighters
Wear self contained breathing apparatus for fire fighting if necessary.

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions
Use personal protective equipment. Avoid dust formation. Avoid breathing dust. Ensure adequate ventilation.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Keep in suitable, closed containers for disposal.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed. Normal measures for preventive fire
protection.
Conditions for safe storage
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Personal protective equipment
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a dust mask type N95 (US) or
type P1 (EN 143) respirator. Use respirators and components tested and approved under appropriate
government standards such as NIOSH (US) or CEN (EU).
Hand protection
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the
standard EN 374 derived from it.
Handle with gloves.
Eye protection
Safety glasses with side-shields conforming to EN166
Skin and body protection
Choose body protection according to the amount and concentration of the dangerous substance at the
work place.
Hygiene measures
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at
the end of workday.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Appearance
Form solid
Safety data
pH no data available
Melting point 227 - 233 °C - lit.
Boiling point no data available
Flash point no data available
Ignition temperature no data available
Lower explosion limit no data available
Upper explosion limit no data available
Water solubility no data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability
Stable under recommended storage conditions.
Conditions to avoid
no data available
Materials to avoid
Strong oxidizing agents
Hazardous decomposition products
Hazardous decomposition products formed under fire conditions. - Carbon oxides

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Section 11. TOXICOLOGICAL INFORMATION
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitization
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
no data available
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. Causes respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. Causes skin irritation.
Eyes Causes eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been thoroughly
investigated.
Additional Information
RTECS: no data available

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Section 12. ECOLOGICAL INFORMATION
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Product
Observe all federal, state, and local environmental regulations. Contact a licensed professional waste
disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn
in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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Section 14. TRANSPORT INFORMATION
ADR/RID
Not dangerous goods
IMDG
Not dangerous goods
IATA
Not dangerous goods

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.

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Section 16. OTHER INFORMATION
Text of H-code(s) and R-phrase(s) mentioned in Section 3
Eye Irrit. Eye irritation
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H335 May cause respiratory irritation.
Skin Irrit. Skin irritation
STOT SE Specific target organ toxicity - single exposure
Xi Irritant
R36/37/38 Irritating to eyes, respiratory system and skin.
Further information
Copyright 2010 Co. License granted to make unlimited paper copies for internal use only.
The above information is believed to be correct but does not purport to be all inclusive and shall be used
only as a guide. The information in this document is based on the present state of our knowledge and is
applicable to the product with regard to appropriate safety precautions. It does not represent any guarantee
of the properties of the product. Co., shall not be held liable for any damage resulting from
handling or from contact with the above product. See reverse side of invoice or packing slip for additional
terms and conditions of sale.

制备方法与用途

生物活性

LC3-mHTT-IN-AN2（化合物AN2）是一种mHTT-LC3连接化合物，能与突变型亨廷顿蛋白(mHTT)和LC3B相互作用，但不与其他野生型亨廷顿蛋白(wtHTT)或无关的对照蛋白相互作用。在体外研究中，LC3-mHTT-IN-AN2（10, 50, 100, 和 300 nM浓度）以等位基因选择性的方式降低了亨廷顿病(HD)小鼠神经元中的mHTT水平。

靶点

mHTT-LC3连接化合物

体外研究

LC3-mHTT-IN-AN2（10, 50, 100, 和 300 nM浓度）在培养的HD小鼠神经元中以等位基因选择性的方式降低了mHTT水平。

反应信息

• 作为反应物：
  描述：

  5,7-二羟基-4-苯基香豆素 在 四氯化锡 、 potassium carbonate 、 magnesium iodide 作用下， 以 二氯甲烷 、 丙酮 、 苯 为溶剂， 反应 96.0h， 生成 7-hydroxy-5-methoxy-4-phenyl-8-tigloylcoumarin
  参考文献：
  名称：

  Sekino, Etsuko; Kumamoto, Takuya; Tanaka, Tomohiro, Journal of Organic Chemistry, 2004, vol. 69, # 8, p. 2760 - 2767

  摘要：

  DOI：
• 作为产物：
  描述：

  5-乙酰氧基-7-甲氧基-4-苯基香豆素 在 氢碘酸 作用下， 生成 5,7-二羟基-4-苯基香豆素
  参考文献：
  名称：

  Ciamician; Silber, Chemische Berichte, 1894, vol. 27, p. 411

  摘要：

  DOI：

文献信息

• Biocatalytic Application of a Membrane‐Bound Coumarin C‐Glucosyltransferase in the Synthesis of Coumarin and Benzofuran C‐Glucosides
  作者：Dawei Chen、Shuai Fan、Zhaoyong Yang、Jungui Dai

  DOI：10.1002/adsc.202100041

  日期：2021.11.23

  been recently identified, whereas the coumarin CGTs have not been found. Here we reported the first identification of a coumarin C-glucosyltransferase MaCGT from Morus alba. The whole-cell biocatalyst harboring MaCGT was exploited and exhibited strictly and efficiently regio- and stereo-specific C-glucosylation capacity toward structurally different coumarins. The whole-cell of MaCGT was further applied

  最近鉴定了许多植物 C-糖基转移酶 (CGT)，而香豆素 CGT 尚未发现。在这里，我们报告了从桑树中首次鉴定出香豆素 C-葡萄糖基转移酶 MaCGT 。对含有 MaCGT 的全细胞生物催化剂进行了开发，并严格有效地展示了针对结构不同的香豆素的区域和立体特异性 C-葡萄糖基化能力。MaCGT的全细胞进一步应用于化学酶法合成苯并呋喃C-葡萄糖苷。此外，MaCGT 被报道为第一个表征的来自植物的膜结合 CGT，尽管序列同源性搜索显示来自M. notabilis 的其他潜在膜结合 CGT; 正如截短的 MaCGT 蛋白的 C-葡萄糖基化活性所证明的那样，跨膜结构域的存在对其催化活性和稳定性至关重要。此外，探索了参与 MaCGT 的 C-糖基化的关键残基。这些发现表明植物界中 CGT 的多样性，并证明了生物催化方法在产生用于药物发现的结构多样的 C-糖苷方面的巨大潜力。
• Alternative two-step route to khellactone analogues using silica tungstic acid and sodium hydrogen phosphate
  作者：Bahador Karami、Saeed Khodabakhshi、Khalil Eskandari

  DOI：10.2478/s11696-013-0411-z

  日期：2013.1.1

  A series of coumarins was synthesised via the silica tungstic acid-catalysed Pechmann reaction; some of these were employed for known three-component reactions with aromatic aldehydes and malononitrile in the presence of sodium hydrogen phosphate (Na2HPO4) as a basic catalyst, affording a variety of potentially anti-HIV active khellactone analogues.

  一系列香豆素通过硅钨酸催化的Pechmann反应合成；其中一些用于已知的三组分反应，与芳香醛和马来酸二腈在存在磷酸氢钠（Na2HPO4）作为碱性催化剂的情况下，生成各种潜在的抗HIV活性的赤花内酯类似物。
• 用于预防或治疗脂质代谢相关疾病的化合物
  申请人：复旦大学

  公开号：CN113549000A

  公开（公告）日：2021-10-26

  本发明涉及生物医药领域，并且具体地涉及将能够结合LC3的结构与能够结合脂滴的结构通过共价连接连接在一起，从而形成的“LC3结合部分‑脂滴结合部分‑偶联物”，其药学上可接受的盐、立体异构体、溶剂化物、多晶型、互变异构体、同位素化合物、代谢产物或前药，以及在制备用于预防或治疗脂质代谢相关疾病的药物中的用途。
• An efficient synthesis of new khellactone-type compounds using potassium hydroxide as catalyst via one-pot, three-component reaction
  作者：B. Karami、K. Eskandari、S. Khodabakhshi

  DOI：10.1007/s13738-013-0333-2

  日期：2014.6

  In the present work, three-component synthesis for novel khellactone-type compounds via the reaction of Meldrum’s acid, aryl aldehydes and 5,7-dihydroxy benzopyrone derivatives was described. In this reaction 10-aryl substituted-9,10-dihydropyrano[2,3-h]benzopyrone-8-ones as new khellactone analogous in the presence of catalytic amount of potassium hydroxide as cheap and green basic catalyst were obtained

  在本工作中，描述了通过Meldrum的酸，芳基醛与5,7-二羟基苯并吡喃酮衍生物的反应合成新颖的Khellactone型化合物的三组分方法。在该反应中，良好地，优异地获得了在便宜的催化量氢氧化钾的存在下，类似于新的内酯的10-芳基取代的9,10-二氢吡喃并[2,3-h]苯并吡喃-8-酮和绿色碱性催化剂。在回流甲醇下收率。
• Skeletal diversity construction via a branching synthetic strategy
  作者：Emma E. Wyatt、Suzanne Fergus、Warren R. J. D. Galloway、Andreas Bender、David J. Fox、Alleyn T. Plowright、Alan S. Jessiman、Martin Welch、David R. Spring

  DOI：10.1039/b607710b

  日期：——

  A branching synthetic strategy was used to efficiently generate structurally diverse scaffolds, which span a broad area of chemical descriptor space, and their biological activity against MRSA was demonstrated.

  一种分支合成策略被用来高效生成结构多样的骨架，覆盖了广泛的化学描述空间，并且证明了它们对耐甲氧西林金黄色葡萄球菌（MRSA）的生物活性。