4,4’-二甲氧基查耳酮 | 2373-89-9

• 物质功能分类: 生物化工 - 提取物
• 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
• 中文名称: 4,4’-二甲氧基查耳酮
• 中文别名: 4,4-二甲氧基查尔酮；4,4'-二甲氧基查耳酮；4,4"-二甲氧基查耳酮
• 英文名称: 4,4'-dimethoxychalcone
• 英文别名: 1,3-bis(4-methoxyphenyl)prop-2-en-1-one；4,4′-dimethoxychalcone；4,4’-dimethoxychalcone；(E)-1,3-bis(4-methoxyphenyl)-2-propen-1-one
• CAS: 2373-89-9
• 化学式: C₁₇H₁₆O₃
• 分子量: 268.312
• InChiKey: HDXVSZWKIHQDES-UHFFFAOYSA-N

物化性质

• 熔点：
  101°C
• 沸点：
  444.6±45.0 °C(Predicted)
• 密度：
  1.128±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：≥250mg/mL（931.76mM）
• 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)：
  3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 安全说明：
  S61
• 危险品运输编号：
  UN 3082 9/PG 3
• WGK Germany：
  3
• 海关编码：
  2914509090
• 危险品标志：
  N
• 危险类别码：
  R51/53
• 包装等级：
  III
• 危险类别：
  9
• 危险性防范说明：
  P201,P264,P280,P301+P330+P331,P312
• 危险性描述：
  H302,H361,H372,H410
• 储存条件：
  请将容器密封后，存放在密闭的储存器中，并放置在阴凉、干燥处。

SDS

---

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 4,4'-DIMETHOXYCHALCONE
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.
CAS-No. : 2373-89-9
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

---

SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute aquatic toxicity (Category 1), H400
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
N Dangerous for the R50/53
environment
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H400 Very toxic to aquatic life.
Precautionary statement(s)
P273 Avoid release to the environment.
Supplemental Hazard none
Statements
Other hazards - none

---

SECTION 3: Composition/information on ingredients
Substances
Formula : C17H16O3
Molecular Weight : 268,32 g/mol
CAS-No. : 2373-89-9
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
4,4'-DIMETHOXYCHALCONE
Aquatic Acute 1; H400 -
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
4,4'-DIMETHOXYCHALCONE
N, R50/53 -
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

---

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

---

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

---

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. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
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.

---

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.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

---

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
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into
the environment must be avoided.

---

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) Evapouration 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- log Pow: 3,741
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

---

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
Strong oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

---

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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

---

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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
Very toxic to aquatic life.
no data available

---

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.

---

SECTION 14: Transport information
UN number
ADR/RID: 3077 IMDG: 3077 IATA: 3077
UN proper shipping name
ADR/RID: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (4,4'-
DIMETHOXYCHALCONE)
IMDG: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (4,4'-
DIMETHOXYCHALCONE)
IATA: Environmentally hazardous substance, solid, n.o.s. (4,4'-DIMETHOXYCHALCONE)
Transport hazard class(es)
ADR/RID: 9 IMDG: 9 IATA: 9
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: yes IMDG Marine pollutant: yes IATA: yes
Special precautions for user
Further information
EHS-Mark required (ADR 2.2.9.1.10, IMDG code 2.10.3) for single packagings and combination
packagings containing inner packagings with Dangerous Goods > 5L for liquids or > 5kg for solids.

---

---

SECTION 15 - REGULATORY INFORMATION
N/A

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

4,4'-Dimethoxychalcone 可从植物当归中分离得到，是一种天然自噬诱导剂，具有抗衰老活性。

靶点

• 自噬 (Autophagy)

体内研究

黄酮类化合物 4,4'-Dimethoxychalcone 在小鼠中表现出抗衰老效果，并且具有心脏保护作用。此外，该物质还有潜力促进多种生物的寿命延长。

在野生型 C57BL/6 小鼠和 Atg4b 缺失 (Atg4b -/-) 小鼠中，通过腹腔注射 100 mg/kg 的 4,4'-Dimethoxychalcone 可有效触发心肌和肝组织中的自噬流。

• 动物模型: 6 周龄野生型 C57BL/6 或 Atg4b -/- 小鼠
• 剂量: 100 mg/kg
• 给药方式: 单次腹腔注射
• 结果: 触发心肌和肝组织中的自噬流

反应信息

• 作为反应物：
  描述：

  4,4’-二甲氧基查耳酮 在 盐酸羟胺 、 sodium acetate 、 2-碘酰基苯甲酸 作用下， 以 氯仿 为溶剂， 反应 4.0h， 以88%的产率得到3,5-bis(4-methoxyphenyl)isoxazole
  参考文献：
  名称：

  邻碘氧基苯甲酸介导合成 3,5-二芳基异恶唑和异恶唑-3-羧酸

  摘要：

  摘要 报道了一种以 α,β-不饱和酮肟为原料合成 3,5-二芳基异恶唑的新型、方便、环保的方法。类似地，还报道了异恶唑羧酸的新合成。这两种方法都使用高效、环保且无毒的碘氧基苯甲酸 (IBX) 作为氧化环化试剂。简单的程序、环境友好的反应条件和无毒是该方法的优点。图形概要

  DOI：

  10.1080/00397911.2013.854916
• 作为产物：
  描述：

  2,3-dibromo-1,3-bis(4-methoxyphenyl)propan-1-one 在 sodium tetrahydroborate 、 nickel dichloride 作用下， 以 甲醇 为溶剂， 反应 0.42h， 以88%的产率得到4,4’-二甲氧基查耳酮
  参考文献：
  名称：

  Stereoselective debromination and selective reduction of vic-dibromides with nickel boride

  摘要：

  报告了在常温下用硼化物镍对沧二溴化物进行立体选择性脱溴反应的简单程序。此外，还报道了脱溴同时还原沧二溴化物以得到二氢化产物的一锅反应。α，β-二溴酮也可以转化为相应的醇。

  DOI：

  10.1139/v06-125

文献信息

• Selective Reduction of α,β-Unsaturated Carbonyl Compounds with CO/H₂O Catalyzed by Selenium under Atmospheric Pressure
  作者：Shiwei Lu、Fengshou Tian

  DOI：10.1055/s-2004-830871

  日期：——

  Selective reduction of α,β-unsaturated carbonyl compounds with carbon monoxide and water in the presence of a catalytic amount of selenium proceeded efficiently to afford the corresponding saturated carbonyl compounds in high yields under atmospheric pressure without use of a base.

  在催化量的硒存在下，α,β-不饱和羰基化合物与一氧化碳和水的选择性还原反应高效进行，无需使用碱，在大气压下即可高产率地得到相应的饱和羰基化合物。
• Metal-free allylation of electron-rich heteroaryl boronic acids with allylic alcohols
  作者：Xue-Dong Li、Li-Jun Xie、De-Long Kong、Li Liu、Liang Cheng

  DOI：10.1016/j.tet.2016.02.047

  日期：2016.4

  cross-coupling of heteroaryl boronic acids with allylic alcohols under catalyst-free reaction conditions is described. The developed procedure is simple, works under external oxidant- and metal-free conditions, and proves to be very general with an unprecedented ortho-selectivity. This approach represents one of the very few examples of ortho-functionalization of boronic acids.

  描述了在无催化剂的反应条件下杂芳基硼酸与烯丙基醇的方便且区域选择性的交叉偶联。所开发的方法很简单，可以在无外部氧化剂和无金属的条件下工作，并且证明是非常通用的，具有空前的邻位选择性。该方法代表了硼酸的邻官能化的极少数实例之一。
• Cellulosic CuI Nanoparticles as a Heterogeneous, Recyclable Catalyst for the Borylation of α,β-Unsaturated Acceptors in Aqueous Media
  作者：Lijie Zhou、Biao Han、Yaoyao Zhang、Bojie Li、Liansheng Wang、Jianying Wang、Xianbao Wang、Lei Zhu

  DOI：10.1007/s10562-021-03571-2

  日期：2021.11

  perform as an efficient heterogeneous catalyst for the synthesis of useful organoboron compounds. Desired β-borylation products were all obtained in good to excellent yields under mild conditions. This catalyst could be recovered easily and still work effectively in six runs. Notably, asymmetric synthesis of organoboron compounds was accomplished by applying a chiral phosphine ligand. This newly developed

  摘要 我们已经证明，纤维素CuI纳米颗粒可以用作合成有用的有机硼化合物的有效多相催化剂。在温和的条件下，均以良好至优异的产率获得了所需的β-硼化产物。该催化剂可以轻松回收，并且在六次运行中仍然可以有效地发挥作用。值得注意的是，有机硼化合物的不对称合成是通过应用手性膦配体完成的。该新开发的方案为形成CB键提供了有效而可持续的途径，并在很大程度上扩展了纤维素的应用范围。 图形概要 有机硼化合物的不对称和有效合成是通过纤维素CuI纳米粒子与手性膦配体的结合完成的。这一新近报道的策略为构建C–B键提供了一种绿色且可持续的方法，并在很大程度上扩展了纤维素的应用范围。
• Highly enantioselective synthesis of γ-substituted butenolides via the vinylogous Mukaiyama–Michael reaction catalyzed by a chiral scandium(iii)–N,N′-dioxide complex
  作者：Qi Zhang、Xiao Xiao、Lili Lin、Xiaohua Liu、Xiaoming Feng

  DOI：10.1039/c1ob05558e

  日期：——

  A highly efficient catalytic asymmetric vinylogous Mukaiyama–Michael reaction of the 2-silyloxyfuran with chalcone derivatives, catalyzed by a chiral N,N′-dioxide–scandium(III) complex, has been accomplished which tolerates a wide range of substrates. The reaction proceeds with complete regioselectivities, excellent diastereoselectivities (up to >99 : 1 dr) and good to excellent enantioselectivities

  2-手性N，N'-二氧化物-scan（III）配合物催化的2-甲硅烷基呋喃与查尔酮衍生物的高效催化不对称乙烯基类化合物的Mukaiyama-Michael反应已经完成，可耐受多种底物。在温和条件下，反应以完全的区域选择性，优异的非对映选择性（最高> 99：1 dr）和良好至优异的对映选择性（最高94％ee）进行，可提供高度官能化的对映异构体富集的抗-γ-取代的丁烯内酯。该过程是耐空气的，并且可以使用现有的试剂轻松地进行操作。为了说明该反应的合成潜力，已研究了克级合成和丁烯内酯的精制。根据实验结果，提出了可能的催化循环和良好的立体识别模型。
• Synthesis and application of modified silica sulfuric acid as a solid acid heterogeneous catalyst in Michael addition reactions
  作者：Mohammad Ali Zolfigol、Hojat Veisi、Farajollah Mohanazadeh、Alireza Sedrpoushan

  DOI：10.1002/jhet.659

  日期：2011.7

  Modified silica sulfuric acid (MSSA) as a new type of silica sulfuric acid was prepared and effectively used in the conjugate addition of indole, pyrrole, and thiols with Michael acceptors under mild conditions at room temperature. Also, MSSA was used as a catalyst for the synthesis of 1,1,3‐tri‐indolyl compounds in good to excellent yield at room temperature. J. Heterocyclic Chem., (2011).

  制备了新型的二氧化硅硫酸改性的二氧化硅硫酸（MSSA），并在室温下于温和条件下有效地用于吲哚，吡咯和硫醇与迈克尔受体的共轭加成中。此外，MSSA还用作催化剂，可在室温下以良好至极好的收率合成1,1,3-三-吲哚基化合物。J.杂环化​​学。（2011）。