3’,4’-二甲氧基黄酮 | 4143-62-8

• 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 - 黄酮类化合物
• 中文名称: 3’,4’-二甲氧基黄酮
• 中文别名: 3',4'-二甲氧基黄酮；3,4-二甲氧基黄酮；3",4"-二甲氧基黄酮
• 英文名称: 3',4'-dimethoxyflavone
• 英文别名: 2-(3,4-dimethoxyphenyl)-4H-chromen-4-one；3',4'-Dimethoxyflavon；3′,4′-dimethoxyflavone；2-(3,4-dimethoxyphenyl)chromen-4-one；3',4′-dimethoxyflavone
• CAS: 4143-62-8
• 化学式: C₁₇H₁₄O₄
• 分子量: 282.296
• InChiKey: ZGHORMOOTZTQFL-UHFFFAOYSA-N

物化性质

• 熔点：
  154-155°C
• 沸点：
  428.5±45.0 °C(Predicted)
• 密度：
  1.242±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：≥20mg/mL
• 最大波长(λmax)：
  334nm(MeOH)(lit.)
• LogP：
  3.650 (est)
• 稳定性/保质期：
  在常温常压下保持稳定

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 安全说明：
  S22,S24/25
• 危险标志：
  GHS06
• 危险性描述：
  H301
• 危险性防范说明：
  P301 + P310
• 海关编码：
  2914509090
• 储存条件：
  请将药品存放在避光、通风干燥的地方，并密封保存。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
: 3′,4′-Dimethoxyflavone
Product name
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. : 4143-62-8
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
Acute toxicity, Oral (Category 3), H301
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
T Toxic R25
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 Danger
Hazard statement(s)
H301 Toxic if swallowed.
Precautionary statement(s)
P301 + P310 IF SWALLOWED: Immediately call a POISON CENTER or doctor/
physician.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Synonyms : 3',4'-DMF; 2-(3,4-Dimethoxyphenyl)-4H-1-benzopyran-4-one
2-(3,4-dimethoxyphenyl)chromen-4-one
Formula : C17H14O4
Molecular Weight : 282,29 g/mol
CAS-No. : 4143-62-8
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
3',4'-DIMETHOXYFLAVONE
Acute Tox. 3; H301 -
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
3',4'-DIMETHOXYFLAVONE
T, R25 -
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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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. Take victim immediately to hospital. 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
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
Wear respiratory protection. 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.
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.
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

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Avoid contact with skin, eyes and clothing. Wash hands before breaks and immediately after handling
the product.
Personal protective equipment
Eye/face protection
Face shield and safety glasses 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
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
Where risk assessment shows air-purifying respirators are appropriate use a full-face particle
respirator type N99 (US) or type P2 (EN 143) respirator cartridges as a backup to engineering
controls. If the respirator is the sole means of protection, use a full-face supplied air respirator. 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.

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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) 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: 3,30
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
Other decomposition products - no data available
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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
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: 2811 IMDG: 2811 IATA: 2811
UN proper shipping name
ADR/RID: TOXIC SOLID, ORGANIC, N.O.S.
IMDG: TOXIC SOLID, ORGANIC, N.O.S. (3',4'-DIMETHOXYFLAVONE)
IATA: Toxic solid, organic, n.o.s. (3',4'-DIMETHOXYFLAVONE)
Transport hazard class(es)
ADR/RID: 6.1 IMDG: 6.1 IATA: 6.1
Packaging group
ADR/RID: III IMDG: III IATA: III
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

3',4'-二甲氧基黄酮是一种脂溶性黄酮，可以从报春花叶中分离得到。这种化合物可以减少PARP的合成与积累，并保护皮层神经元免受Parthanatos诱导的细胞死亡。此外，3',4'-二甲氧基黄酮还能作为人类乳腺癌细胞中的芳基碳氢化合物受体拮抗剂。同时，它能够促进人造血干细胞的增殖。3',4'-二甲氧基黄酮具有多种生物活性，包括抗氧化、抗癌、抗炎、抗动脉粥样硬化、降血脂和神经保护或神经营养作用等。

反应信息

• 作为反应物：
  描述：

  3’,4’-二甲氧基黄酮 在 氢氧化钾 、 三氯化铝 作用下， 以 水 、 乙腈 为溶剂， 反应 23.0h， 生成 3',4'-(2'',3''-dihydro-1'',4''-dioxino)flavone
  参考文献：
  名称：

  Ahmed; Khan; Alam, Pharmazie, 2003, vol. 58, # 3, p. 173 - 176

  摘要：

  DOI：
• 作为产物：
  描述：

  4-碘藜芦醚 在 4-二甲氨基吡啶 、 Iron(III) nitrate nonahydrate 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 正丁基锂 、 2,2,6,6-四甲基哌啶氧化物 、 氧气 、 三乙胺 、 sodium chloride 、 potassium hydroxide 作用下， 以 四氢呋喃 、 正己烷 、 甲苯 、 乙腈 为溶剂， 反应 62.7h， 生成 3’,4’-二甲氧基黄酮
  参考文献：
  名称：

  铁催化好氧氧化反应及随后的4-二甲基氨基吡啶催化6-内酯环化反应一锅合成γ-苯并吡喃酮

  摘要：

  通过铁催化的好氧氧化和4-二甲基氨基吡啶催化的相关炔丙醇的环化反应，可以实现一锅合成γ-苯并吡喃酮的高产和极好的区域选择性。还已经实现了芳族取代的γ-苯并吡喃酮的衍生化和天然存在的3'，4'-二甲氧基黄酮的合成。

  DOI：

  10.1002/adsc.201700993

文献信息

• Identification and structure activity relationship of novel flavone derivatives that inhibit the production of nitric oxide and PGE 2 in LPS-induced RAW 264.7 cells
  作者：Ji-Young An、Hwi-Ho Lee、Ji-Sun Shin、Hyung-Seok Yoo、Jong Seon Park、Seung Hwan Son、Sang Won Kim、Jihyun Yu、Jun Lee、Kyung-Tae Lee、Nam-Jung Kim

  DOI：10.1016/j.bmcl.2017.03.057

  日期：2017.6

  In an effort to identify novel anti-inflammatory compounds, a series of flavone derivatives were synthesized and biologically evaluated for their inhibitory effects on the production of nitric oxide (NO) and prostaglandin E2 (PGE2), representative pro-inflammatory mediators, in LPS-induced RAW 264.7 cells. Their structure-activity relationship was also investigated. In particular, we found that compound

  为了鉴定新型抗炎化合物，合成了一系列黄酮衍生物，并对其在LPS-中对代表性的促炎性介质一氧化氮（NO）和前列腺素E2（PGE2）产生的抑制作用进行了生物学评估。诱导的RAW 264.7细胞。还研究了它们的构效关系。尤其是，我们发现与木犀草素（一种被称为强效抗炎剂的天然黄酮）相比，化合物3g对PGE2的产生显示出更强的抑制活性，对NO生成具有类似的抑制活性，并且细胞毒性也较弱。
• A practical synthesis of flavones from methyl salicylate
  作者：Dhanapalan Nagarathnam、Mark Cushman

  DOI：10.1016/s0040-4020(01)87119-2

  日期：1991.1

  A facile synthetic method has been developed for the conversion of methyl salicylate (5) into flavones 1a-i in high yields. Compound 5 on treatment with t-butyldimethylsilyl chloride (6) gave the O-silyl protected ester 7. Condensation of this ester 7 with the lithium anion generated from acetophenones 3a-i yielded the 1.3-diarylpropane-1,3-diones 8a-i, which on treatment with glacial acetic acid containing

  已经开发了一种简便的合成方法，用于将水杨酸甲酯（5）以高收率转化为黄酮1a-i。用叔丁基二甲基甲硅烷基氯（6）处理化合物5，得到O-甲硅烷基保护的酯7。将该酯7与由苯乙酮3a -i生成的锂阴离子进行缩合，得到1.3-二芳基丙烷-1,3-二酮8a-i，将其用含0.5％H 2 SO 4的冰醋酸在95- ℃处理3小时。 100°C以83–94％的收率提供了所需的黄酮1a-i。
• Experimental and theoretical insights into the photophysical and electrochemical properties of flavone-based hydrazones
  作者：Meshari A. Alsharif、Nafeesa Naeem、Ehsan Ullah Mughal、Amina Sadiq、Rabab.S. Jassas、Samia Kausar、Ataf Ali Altaf、Muhammad Naveed Zafar、Amara Mumtaz、Rami J. Obaid、Reem I. Alsantali、Safeer Ahmed、Ishtiaq Ahmed、Hatem M. Altass、Saleh A. Ahmed

  DOI：10.1016/j.molstruc.2021.130965

  日期：2021.11

  with 2,4-dinitrophenylhydrazine (2,4-DNPH) and characterized by different spectral techniques (IR, UV–Vis, NMR and mass spectrometry). The electrochemical, photophysical and theoretical investigations of such type of compounds are hitherto unknown. The electrochemical behavior of these hydrazones at a platinum electrode has been analyzed by cyclic voltammetry (CV) and was investigated at 200, 100 and 40

  已经设计、合成和表征了基于黄酮的腙的小型文库。在此背景下，通过黄酮与 2,4-二硝基苯肼 (2,4-DNPH) 的酸催化缩合合成了13 种黄酮腙(3a-3  m)，并通过不同的光谱技术（IR、UV-Vis、NMR和质谱）。这种类型的化合物的电化学、光物理和理论研究迄今为止是未知的。这些腙在铂电极上的电化学行为已通过循环伏安法 (CV) 进行分析，并在 200、100 和 40 mVs -1的乙腈 (CH 3CN)。这些腙显示出准可逆的氧化还原反应。这些衍生物的氧化还原反应位点通过几何优化使用密度泛函理论 (DFT) 在 Guassian-09 理论水平的 B3LYP/3-21 g 下定位。此外，目标化合物表现出有趣的荧光特性。由于其优异的光物理和氧化还原结果，建立了详细的结构-性质关系以评估取代基的影响及其对物理化学和电子性质的位置。所有的实验结果都与计算研究一致。
• Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalcones <i>via</i> palladium(<scp>ii</scp>)-catalyzed oxidative cyclization
  作者：Seung Hwan Son、Yang Yil Cho、Hyung-Seok Yoo、Soo Jin Lee、Young Min Kim、Hyu Jeong Jang、Dong Hwan Kim、Jeong-Won Shin、Nam-Jung Kim

  DOI：10.1039/d1ra01672e

  日期：——

  Divergent and versatile synthetic routes to flavones and flavanones via efficient Pd(II) catalysis are disclosed. These Pd(II) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives, via discriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic

  公开了通过有效的 Pd( II ) 催化合成黄酮和黄烷酮的不同且通用的合成路线。根据氧化剂和添加剂，这些 Pd( II ) 催化剂分别以高度原子经济的方式通过涉及脱氢的区分氧化环化序列，方便地从 2'-羟基二氢查耳酮中提供各种黄酮和黄烷酮作为常见的中间体。
• Syntheses of Flavones via the Iodine-Mediated Oxidative Cyclization of 1,3-Diphenylprop-2-en-1-ones
  作者：Hideyoshi Miyake、Eizo Takizawa、Mitsuru Sasaki

  DOI：10.1246/bcsj.76.835

  日期：2003.4

  The syntheses of flavones from 1,3-diphenylporp-2-ene-1-ones are described. When 1,3-diphenylprop-2-en-1-ones were heated with iodine in triethylene glycol, oxidative cyclization underwent to obtain flavones in good yields.

  描述了从 1,3-diphenylporp-2-ene-1-ones 合成黄酮。当 1,3-二苯基丙-2-烯-1-酮与碘在三甘醇中加热时，进行氧化环化，以良好的收率获得黄酮。