6-羟基-4-甲基香豆素 | 2373-31-1

• 物质功能分类: 化学试剂 - 有机试剂 - 双环化合物
• 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: 6-羟基-4-甲基香豆素
• 英文名称: 6-hydroxy-4-methyl-chromen-2-one
• 英文别名: 6-hydroxy-4-methylcoumarin；6-hydroxy-4-methyl-2H-chromen-2-one；6-hydroxy-4-methylchromen-2-one
• CAS: 2373-31-1
• 化学式: C₁₀H₈O₃
• mdl: MFCD00016967
• 分子量: 176.172
• InChiKey: IRUHWRSITUYICV-UHFFFAOYSA-N

物化性质

• 熔点：
  246.5-249.5 °C(lit.)
• 沸点：
  391.4±37.0 °C(Predicted)
• 密度：
  1.319±0.06 g/cm3(Predicted)
• 稳定性/保质期：
  避免让氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• RTECS号：
  GN6999800
• 海关编码：
  2932209090
• 危险性防范说明：
  P264,P280,P302+P352+P332+P313+P362+P364,P305+P351+P338+P337+P313
• 危险性描述：
  H315,H319
• 储存条件：
  储存在阴凉、干燥的地方，并远离热源和不相容物质；需密封保存并在通风良好的环境中存放。

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : 6-Hydroxy-4-methylcoumarin
CAS-No. : 2373-31-1
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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Section 2. HAZARDS IDENTIFICATION
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP]
Skin irritation (Category 2)
Eye irritation (Category 2)
Specific target organ toxicity - single exposure (Category 3)
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Irritating to eyes, respiratory system and skin.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
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.
Supplemental Hazard none
Statements
According to European Directive 67/548/EEC as amended.
Hazard symbol(s)
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
Substances
Formula : C10H8O3
Molecular Weight : 176,17 g/mol
Component Concentration
6-Hydroxy-4-methyl-2-benzopyrone
CAS-No. 2373-31-1 -
EC-No. 219-146-3

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Section 4. FIRST AID MEASURES
Description of 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.
Most important symptoms and effects, both acute and delayed
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Indication of any immediate medical attention and special treatment needed
no data available

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Section 5. FIREFIGHTING MEASURES
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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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, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end uses
no data available

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Section 8. EXPOSURE CONTROLS/PERSONAL PROTECTION
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Body Protection
impervious clothing, The type of protective equipment must be selected according to the
concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing Melting point/range: 246,5 - 249,5 °C - lit.
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evaporation rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Autoignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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Section 10. STABILITY AND REACTIVITY
Reactivity
no data available
Chemical stability
no data available
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available

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Section 11. TOXICOLOGICAL INFORMATION
Information on toxicological effects
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 serious 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: Not 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
Results of PBT and vPvB assessment
no data available
Other adverse effects
no data available

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Section 13. DISPOSAL CONSIDERATIONS
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. 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
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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Section 15. REGULATORY INFORMATION
This safety datasheet complies with the requirements of Regulation (EC) No. 1907/2006.
Safety, health and environmental regulations/legislation specific for the substance or mixture
no data available
Chemical Safety Assessment
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 Co. LLC. 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. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

概述

6-羟基-4-甲基香豆素属于香豆素类化合物的一种。这类化合物拥有多种生物活性，包括抗凝血、抗肿瘤、抗病毒、增强自身免疫能力、抑制细胞增生、抗菌、抗艾滋病、抗疲劳及钙拮抗等功效。

用途

6-羟基-4-甲基香豆素是一种有机化合物，具有多样的药理作用，可广泛应用于医药生产中。

生物活性

6-羟基-4-甲基香豆素（化合物9）是香豆素的次级代谢产物，并展现出显著的抗癌活性。

反应信息

• 作为反应物：
  描述：

  6-羟基-4-甲基香豆素 在 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到6-chloro-4-methyl-2H-chromen-2-one
  参考文献：
  名称：

  Microwave-Assisted Synthesis of Novel 2H-Chromene Derivatives Bearing Phenylthiazolidinones and Their Biological Activity Assessment

  摘要：

  制备了 6-羟基-2-氧代-2H-苯并吡喃-4-甲醛 (2)、6-氯-2-氧代-2H-苯并吡喃-4-甲醛 (3) 和 6-肼基-4-甲基-2H-苯并吡喃-2-酮 (5)，作为单药效基团关键中间体。在微波辅助和传统化学合成工艺下，将化合物 2、3 和 5 加入一系列多组分反应 (MCR)，以良好的产率获得了一系列三和/或四药效基团共轭物 8a、b、11、13、16、17、19 和 20。新合成的化合物通过红外光谱、核磁共振、13C-核磁共振、质谱和元素分析进行了表征。最后，对合成的化合物进行了生物活性筛选，结果表明它们对不同种类的细菌和真菌具有显著的抗菌活性。

  DOI：

  10.3390/molecules191219648
• 作为产物：
  描述：

  6-烯丙氧基-4-甲基-色烯-2-酮 在 palladium on activated charcoal ammonium formate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以95%的产率得到6-羟基-4-甲基香豆素
  参考文献：
  名称：

  使用钯/炭催化剂和甲酸铵对苯酚和羟基香豆素的烯丙基醚进行温和有效的脱保护

  摘要：

  描述了一种催化量为10％的Pd / C与甲酸铵相结合的烯丙基苯基醚和烯丙基香豆基醚裂解的有效方法。酚的烯丙基醚比醇的烯丙基醚优先脱保护，并且该方法与几种可还原的官能团如CHO，COCH 3，CO 2 Et和NHCOCH 3相容。

  DOI：

  10.1016/j.tetlet.2006.05.176

文献信息

• Supramolecular Control of the Template-Induced Selective Photodimerization of 4-Methyl-7-O-hexylcoumarin
  作者：William G. Skene、Emilie Couzigné、Jean-Marie Lehn

  DOI：10.1002/chem.200305268

  日期：2003.11.21

  are capable of binding substrates with complementary donor and acceptor sites to form a supramolecular complex through hydrogen bonding. Receptor 3 was designed to accept two guest molecules, which are held in close proximity within the supramolecular species. The substrate molecule, 4-methyl-7-O-hexylcoumarin (1 c), forms a 2:1 complex with a binding constant of 150 m(-1) for the second substrate

  设计并合成了包含两个相同的氢键识别亚基的对称的对位分子受体（3）。这些亚基能够结合具有互补供体和受体位点的底物以通过氢键形成超分子复合物。受体3被设计为接受两个客体分子，它们紧密地保持在超分子物种内。底物分子4-甲基-7-O-己基香豆素（1 c）与第二种底物形成2：1配合物，其结合常数为150 m（-1），首先通过1：1配合物与亲和常数510 m（-1）。当1 c的两个分子与模板结合时，其取向会导致在照射时选择性形成反式[2 + 2]光合产物2 cB。
• 신규한 쿠마린 유도체 및 이의 제조방법
  申请人：GREEN CROSS MEDIS Corp. 주식회사 녹십자메디스(120090236968) Corp. No ▼ 135111-0087407BRN ▼410-81-93457

  公开号：KR101620093B1

  公开（公告）日：2016-05-13

  본 발명은 신규한 쿠마린 유도체 및 이의 제조방법에 관한 것이다. 본 발명에 따른 쿠마린 유도체는 수용액에서 용해도가 우수하고 형광을 갖는 쿠마린 모체에 아미노페닐보론산을 도입함으로써, 당화혈색소와 높은 결합력을 갖는 보론산에 의해 혈액 속에 있는 당화혈색소와 결합력이 높아져 혈액 속의 당화혈색소 존재 유무를 선택적 발광성을 통해 확인할 수 있으며, 당화혈색소의 인지 능력을 증대시킬 수 있다. 따라서, 본 발명에 따른 쿠마린 유도체는 당화혈색소에 대하여 선택적 결합력이 있고 결합 전후에 형광 변화를 나타낼 수 있으므로, 혈액에서 당화혈색소 검출용 센서로 유용하게 사용될 수 있다.

  本发明涉及一种新型的荧光标记的胆固醇衍生物及其制造方法。根据本发明，通过在胆固醇母体上引入氨基苯甲酸，所得到的胆固醇衍生物在水溶液中具有优异的溶解度和荧光性。由于衍生物中的苯甲酸部分与糖化血红蛋白具有高亲和力，因此能够与血液中的糖化血红蛋白强烈结合。这使得可以通过其选择性的荧光变化来检测血液中糖化血红蛋白的存在与否，并提高对糖化血红蛋白的识别能力。因此，本发明中的胆固醇衍生物对于糖化血红蛋白具有选择性结合能力，并在结合前后显示出荧光变化，因此可用于血液中糖化血红蛋白检测的传感器。
• Cross-Coupling of Amide and Amide Derivatives to Umbelliferone Nonaflates: Synthesis of Coumarin Derivatives and Fluorescent Materials
  作者：Shane M. Hickey、Samuel O. Nitschke、Martin J. Sweetman、Christopher J. Sumby、Douglas A. Brooks、Sally E. Plush、Trent D. Ashton

  DOI：10.1021/acs.joc.0c00813

  日期：2020.6.19

  properties of aqueous-soluble derivatives were determined, and they displayed auxochrome-based variations. Gram-scale synthesis provided an acrylamide analogue, which was used to fabricate a fluorescent poly(2-hydroxylethyl methacrylate) (pHEMA) hydrogel that was resistant to leaching in ultrapure H2O. We envisage that our reported protocol to access 7-amino-4-methylcoumarin derivatives will find use toward

  描述了4-甲基伞形酮衍生的壬二酸酯与酰胺，氨基甲酸酯和磺酰胺之间的布赫瓦尔德-哈特维格交叉偶联反应。以良好至优异的产率制备了多种N-取代的7-氨基香豆素类似物。测定了水溶性衍生物的光物理性质，并且它们显示出基于色素的变化。克级合成提供了一种丙烯酰胺类似物，该丙烯酰胺类似物用于制造可抵抗超纯H 2 O浸出的荧光聚（甲基丙烯酸2-羟乙酯）（pHEMA）水凝胶。我们设想，我们报告的访问7-氨基-该领域的研究人员将发现4-甲基香豆素衍生物可用于开发基于荧光香豆素的新型荧光探针。
• Quaternary ammonium and amido derivatives of pyranochromenones and chromenones: synthesis and antimicrobial activity evaluation
  作者：Suchita Prasad、Shiv Kumar、Bipul Kumar、Abhishek Kumar Singh、Hemant K. Gautam、Sunil K. Sharma

  DOI：10.1007/s00044-014-1294-4

  日期：2015.6

  of their resistance to antimicrobial agents are alarming issues worldwide and consistent efforts are being made to develop efficient antimicrobial agents. In this perspective, a series of novel ammonium and amide derivatives of pyranocoumarin and coumarin were synthesized and evaluated for their antimicrobial activity. Among them, six compounds exhibited significant activity against gram-positive bacteria

  传染性疾病及其对抗菌剂的抗性发展是世界范围内令人震惊的问题，并且人们一直在努力开发有效的抗菌剂。从这个角度出发，合成了一系列新颖的吡喃香豆素和香豆素铵和酰胺衍生物，并对其抗菌活性进行了评估。其中，六种化合物对革兰氏阳性细菌蜡状芽孢杆菌（MTCC 430）和枯草芽孢杆菌（MTCC 121）和革兰氏阴性细菌铜绿假单胞菌（MTCC 741）表现出显着活性。化合物N，N，N-三乙基-10-（4,8,8-三甲基-2-氧代-2,6,7,8-四氢吡喃[3,2 - g ]铬基-10-基氧基）癸1 -溴化铵（16）在MDA中表现出最高的抗菌活性，MIC值为5μg/ ml。化合物17和18对MDA中的红毛癣菌（临床分离株）表现出中等的抗真菌活性，MIC为6.25μg/ ml 。溶血分析结果表明，六分之三的化合物各自的MIC值是安全的。这些结果为进一步优化用于设计下一代化合物作为先导抗菌剂的支架提供了见识。
• [EN] NOVEL CHROMEN-2-ONE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS<br/>[FR] NOUVEAUX DERIVES DE CHROMENE-2-ONE ET LEUR UTILISATION COMME INHIBITEURS DE RECAPTURE DU NEUROTRANSMETTEUR MONOAMINE
  申请人：NEUROSEARCH AS

  公开号：WO2006035034A1

  公开（公告）日：2006-04-06

  This invention relates to novel chromen-2-one derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy and to pharmaceutical compositions comprising the compounds of the invention.

  本发明涉及作为单胺类神经递质再摄取抑制剂的有用的新喹诺酮-2-酮衍生物。在其他方面，本发明涉及将这些化合物用于治疗方法中的用途，以及包含本发明化合物的药物组合物。

表征谱图