1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one | 39273-61-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one
• 英文别名: 2'-hydroxy-4'-methoxychalcone；2′-hydroxy-4′-methoxychalcone；4'-Methoxy-2'-hydroxy chalcone
• CAS: 39273-61-5
• 化学式: C₁₆H₁₄O₃
• mdl: MFCD00017173
• 分子量: 254.285
• InChiKey: GUNGQVJAKLIYDG-UHFFFAOYSA-N

物化性质

• 熔点：
  106 °C
• 沸点：
  454.6±45.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2914509090

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 2'-Hydroxy-4'-Methoxychalcone
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
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
Not a hazardous substance or mixture according to Regulation (EC) No. 1272/2008.
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.

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SECTION 3: Composition/information on ingredients
Substances
Molecular weight : 254,29 g/mol
No components need to be disclosed according to the applicable regulations.

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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
Flush eyes with water as a precaution.
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
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
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
Nature of decomposition products not known.
Advice for firefighters
Wear self-contained breathing apparatus for firefighting 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 vapours, mist or gas. Avoid
breathing dust.
For personal protection see section 8.
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 formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Storage class (TRGS 510): Non Combustible Solids
Specific end use(s)
Apart from the uses mentioned in section 1.2 no other specific uses are stipulated

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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
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
Choose body protection in relation to its type, to the concentration and amount of dangerous
substances, and to the specific work-place., The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Respiratory protection is not required. Where protection from nuisance levels of dusts are desired,
use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and
approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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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 No data available
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) Auto-ignition 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
Stable under recommended storage conditions.
Possibility of hazardous reactions
No data available
Conditions to avoid
No data available
Incompatible materials
No data available
Hazardous decomposition products
In the event of fire: see section 5

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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 sensitisation
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
No data available
Specific target organ toxicity - repeated exposure
No data available
Aspiration hazard
No data available
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
This substance/mixture contains no components considered to be either persistent, bioaccumulative and
toxic (PBT), or very persistent and very bioaccumulative (vPvB) at levels of 0.1% or higher.
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. 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
For this product a chemical safety assessment was not carried out

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SECTION 16: Other information
Further information
Copyright 2014 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.

反应信息

• 作为反应物：
  描述：

  1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one 在 高氯酸 、 thallium(III) nitrate 作用下， 以 甲醇 、 氯仿 为溶剂， 生成 7-甲氧基异黄酮
  参考文献：
  名称：

  One-step conversion of flavanones into isoflavones: a new facile biomimetic synthesis of isoflavones

  摘要：

  DOI：

  10.1016/s0040-4039(00)88565-2
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 在 potassium carbonate 、 potassium hydroxide 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 9.0h， 生成 1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  基于磷酸盐和硫代磷酸黄酮类似物的类固醇硫酸酯酶抑制剂。

  摘要：

  临床前研究

  DOI：

  10.1002/ddr.21281
• 作为试剂：
  描述：

  1-(2-oxo-2-phenylethyl)-1H-pyrrole-2-carbaldehyde 在 1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one 、 caesium carbonate 作用下， 以 2-甲基四氢呋喃 为溶剂， 反应 2.0h， 生成 1-(5-benzoyl-6-phenylindolizin-7-yl)-1H-pyrrole-2-carbaldehyde
  参考文献：
  名称：

  通过 [5+1] 环比获得吡啶合成多功能化吲哚嗪

  摘要：

  在Cs 2 CO 3存在下，通过由2-羟基苯乙酮和吡咯衍生物[5+1]环状构建吡啶，实现了吲哚嗪的吡啶基序的多功能化。建议该反应通过多米诺醛醇-氧杂迈克尔-迈克尔-消除-氧化过程进行，导致在吲哚嗪的 C5、C6 和 C7 位置安装三个不同的官能团。溶剂 (2-MeTHF) 和 2-羟基苯乙酮的羟基似乎对这一成功的环化事件起着至关重要的作用。还证明了对所得支架的进一步阐述和使用其他甲基酮对本协议的扩展。

  DOI：

  10.1002/adsc.202100844

文献信息

• Single and double intramolecular proton transfers in the electronically excited state of flavone derivatives
  作者：I. E. Serdiuk、A. D. Roshal

  DOI：10.1039/c5ra13912k

  日期：——

  to take part in Excited State Intramolecular Double Proton Transfer (ESIDPT), we synthesized two carbonyl derivatives of 3,7-dihydroxyflavone, both containing two different proton-transfer sites as well as related carbonyl derivatives of 3-hydroxyflavone and 7-hydroxyflavone. All the examined hydroxyflavones were found to participate in the Excited State Intramolecular Proton Transfer (ESIPT). ESIPT

  为了创建能够参与激发态分子内双质子转移（ESIDPT）的黄酮衍生物，我们合成了3,7-二羟基黄酮的两个羰基衍生物，它们都包含两个不同的质子转移位点以及相关的3-羟基黄酮和7-羟基黄酮。发现所有检查的羟基黄酮均参与兴奋态分子内质子转移（ESIPT）。与涉及7-羟基和6 / 8-羰基片段的ESIPT相比，涉及3-羟基和4-羰基的ESIPT具有更高的阻隔性。根据提供的数据，3,7-二羟基-2-苯基-6-（3-苯基丙酰基）-4 H-chromen-4-one经历两阶段的ESIDPT，形成中间互变异构体。这种ESIDPT会导致互变异构形式，其激发态的辐射失活速率异常低，从而限制了低荧光量子产率。3,7-二羟基-4-氧代-2-苯基-4 H-亚甲基-8-甲醛在电子激发态下的行为类似于3-羟基黄酮衍生物，因此我们推断该化合物中存在单个ESIPT 。
• Arylalkyl Ketones, Benzophenones, Desoxybenzoins and Chalcones Inhibit TNF-α Induced Expression of ICAM-1: Structure-Activity Analysis
  作者：Sarvesh Kumar、Chandra Shekhar Reddy L、Yogesh Kumar、Amit Kumar、Brajendra K. Singh、Vineet Kumar、Shashwat Malhotra、Mukesh K. Pandey、Rajni Jain、Rajesh Thimmulappa、Sunil K. Sharma、Ashok K. Prasad、Shyam Biswal、Erik Van der Eycken、Anthony L. DePass、Sanjay V. Malhotra、Balaram Ghosh、Virinder S. Parmar

  DOI：10.1002/ardp.201100279

  日期：2012.5

  potent intercellular cell adhesion molecule‐1 (ICAM‐1) inhibitors, a large number of arylalkyl ketones, benzophenones, desoxybenzoins and chalcones and their analogs (54 in total) have been synthesized and screened for their ICAM‐1 inhibitory activity. The structure‐activity relationship studies of these compounds identified three potent chalcone derivatives and also demonstrated the possible mechanism

  白细胞和血管内皮细胞 (EC) 之间通过细胞粘附分子的相互作用在各种炎症和自身免疫性疾病的发病机制中起着重要作用。阻断这些相互作用的小分子已成为针对急性和慢性炎症疾病的潜在治疗剂。为了鉴定有效的细胞间细胞粘附分子-1 (ICAM-1) 抑制剂，已经合成了大量的芳烷基酮、二苯甲酮、脱氧安息香和查耳酮及其类似物（共 54 种），并筛选了它们的 ICAM-1 抑制剂活动。这些化合物的构效关系研究确定了三种有效的查耳酮衍生物，并证明了其 ICAM-1 抑制活性的可能机制。
• 一种2-取代苯并吡喃-4-酮类化合物及其应用
  申请人：中国人民解放军第二军医大学

  公开号：CN105669625B

  公开（公告）日：2018-05-25

  本发明涉及医药技术领域，公开了一类具有通式I结构的2‑取代苯并吡喃‑4‑酮类化合物及其在制备抗真菌和协同抗真菌药物中的应用。该类化合物可以与氮唑类抗真菌药物共同使用，可提高耐药菌对氮唑类药物的敏感性，实现逆转耐药作用，产生协同抗真菌作用。
• Biocatalytic green alternative to existing hazardous reaction media: synthesis of chalcone and flavone derivatives <i>via</i> the Claisen–Schmidt reaction at room temperature
  作者：Kashyap J. Tamuli、Ranjan K. Sahoo、Manobjyoti Bordoloi

  DOI：10.1039/d0nj03839c

  日期：——

  Hook. F. peel ash (MCPA) are used as catalysts to promote an inexpensive, efficient and eco-friendly carbon–carbon bond forming crossed aldol reaction at room temperature in solvent free conditions. Furthermore, the resulting products were subjected to reactions with these promoters in an oxygen atmosphere and led to the formation of novel flavone derivatives. Moreover, the used catalysts were properly

  由于全球废料数量的增加，将废料或次级副产品转化为用于各种应用的增值产品引起了人们的极大兴趣。在此，两种新颖的农业食品废品Musa sp。``马尔堡''果皮灰（MMPA）和Musa Champa霍特 前钩。F.果皮灰（MCPA）用作催化剂，可促进在室温下无溶剂条件下廉价，高效且生态友好的碳-碳键形成交叉羟醛反应。此外，在氧气气氛中使所得产物与这些促进剂反应，并导致形成新的黄酮衍生物。此外，使用不同的复杂分析技术，例如傅立叶变换红外光谱（FT-IR），X射线衍射法（XRD），Brunauer-Emmett-Teller分析（BET），拉曼光谱，扫描电子显微镜，对用过的催化剂进行了适当的表征。能量色散X射线光谱（SEM-EDS），过渡电子显微镜（TEM），X射线光电子能谱（XPS）和热重分析（TGA）以及使用原子吸收光谱和离子色谱法的元素检测。这两种方法均不含金属，并且不含任何额外的添加剂，助催
• Ultrasound assisted synthesis and cytotoxicity evaluation of known 2′,4′-dihydroxychalcone derivatives against cancer cell lines
  作者：Joan Villena、Iván Montenegro、Bastian Said、Enrique Werner、Susana Flores、Alejandro Madrid

  DOI：10.1016/j.fct.2021.111969

  日期：2021.2

  This work reports on the development of an efficient and ecofriendly ultrasound assisted method for the high yield synthesis (70.0-94.0%) of eighteen oxyalkylated derivatives of 2',4'-dihydroxychalcone. Synthesized compounds were subjected to in vitro biological assays against HT-29 (colorectal), MCF-7 (breast), and PC-3 (prostate) human tumor cell lines, these cell lines are among the ten most aggressive

  这项工作报告了一种高效，环保的超声辅助方法的开发，该方法可以高产率地合成18种2'，4'-二羟基查耳酮的烷氧基化衍生物（70.0-94.0％）。对合成的化合物进行了针对HT-29（结肠直肠），MCF-7（乳腺癌）和PC-3（前列腺）人类肿瘤细胞系的体外生物学分析，这些细胞系是世界上诊断出的十种最具侵袭性的恶性肿瘤之一。细胞毒性评估表明，四种合成的化合物对MCF-7（IC 50 = 8.4–34.3μM）和PC-3（IC 50 = 9.3-29.4μM）表现出中等至非常高的毒性，与5-氟尿嘧啶（IC 5016.4–22.3μM）。相同的化合物仅对HT-29（IC 50 15.3-36.3μM）具有中等活性，接近柔红霉素（IC 50 15.1μM ）。接着，尽管化合物的选择性指数（SI）较弱，但化合物18对癌细胞显示出显着的选择性细胞毒性活性（5.8-10.57）。除此以外，大多数化合物显着降