红陪酚四甲基醚 | 6273-57-0

• 分子结构分类: 有机化合物 - 碳氢化合物衍生物 - 环庚三烯酮
• 中文名称: 红陪酚四甲基醚
• 中文别名: 红酚四甲基醚
• 英文名称: 2,3,4,6-tetramethoxy-5H-benzo[7]annulen-5-one
• 英文别名: Tetra-O-methyl-purpurogallin；tetramethyl purpurogallin；Purpurogallin-tetramethylether；2,3,4,6-Tetramethoxybenzo[7]annulen-5-one
• CAS: 6273-57-0
• 化学式: C₁₅H₁₆O₅
• 分子量: 276.289
• InChiKey: ZEEDZJJOWWIIFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Purpurogallin tetramethyl ether
CAS-No. : 6273-57-0
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
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Formula : C15H16O5
Molecular Weight : 276,28 g/mol

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Section 4. FIRST AID MEASURES
Description of first aid measures
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration.
In case of skin contact
Wash off with soap and plenty of water.
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.
Most important symptoms and effects, both acute and delayed
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
Avoid dust formation. Avoid breathing vapors, mist or gas.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
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
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
General industrial hygiene practice.
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).

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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 90 - 92 °C
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
no data available
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Potential health effects
Inhalation May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
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.
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  红陪酚四甲基醚 在 盐酸 作用下， 以 苯 为溶剂， 生成 5,6,7-Trimethoxy-2,3-ethanoindan-1,8-dion
  参考文献：
  名称：

  托洛酮的光转化。第六部分 苄酮系列的新重排

  摘要：

  四-O-甲基紫purogallin的非水溶液的紫外线照射导致两个新的重排。在无水乙醇中，唯一分离出的产物是1-羟基-6,7,8-三甲氧基萘，在各种非质子溶剂中，萘酚伴随有新颖结构的三环酮。

  DOI：

  10.1039/j39680001149
• 作为产物：
  描述：

  亚硫酸二甲酯 、 4,2',3'-trimethylpurpurogallin 在 sodium hydroxide 作用下， 生成 红陪酚四甲基醚
  参考文献：
  名称：

  二氮杂双环苯并恶臭酮衍生物的合成及其体外原杀生物活性。

  摘要：

  我们描述了基于苯并二氮杂环戊烷醚的一系列二氮杂双环类化合物的合成和原杀生物评价。可以通过使用简单易得的起始原料通过高产率的异Diels-Alder反应获得的几种化合物在体外对克氏锥虫和杜氏利什曼原虫具有体外活性，这些活性可与之媲美，在某些情况下还优于后者。当前使用的化学疗法。

  DOI：

  10.1016/j.bmcl.2007.05.044

文献信息

• Discovery of Small-Molecule Inhibitors of the TLR1/TLR2 Complex
  作者：Kui Cheng、Xiaohui Wang、Shuting Zhang、Hang Yin

  DOI：10.1002/anie.201204910

  日期：2012.12.3

  An important regulator of innate immunity, the protein complex of Toll‐like receptors 1 and 2 (TLR1/TLR2) provides an attractive target for the treatment of various immune disorders. The novel compound CU‐CPT22 can compete with the binding of the specific lipoprotein ligand to TLR1/TLR2 (see picture) with high inhibitory activity and specificity. Repression of downstream signaling from TNF‐α and IL‐1β

  作为先天免疫的重要调节剂， Toll 样受体 1 和 2 (TLR1/TLR2) 的蛋白质复合物为治疗各种免疫疾病提供了一个有吸引力的靶点。新型化合物 CU-CPT22 可以与特异性脂蛋白配体竞争结合 TLR1/TLR2（见图），具有高抑制活性和特异性。还观察到来自 TNF-α 和 IL-1β 的下游信号受到抑制。
• Formation of two benzocyclo-octatrienedione and 2,3-benzohomotropone derivatives by dichlorocarbene ring expansion
  作者：Josuke Tsunetsugu、Masaru Sato、Seiji Ebine

  DOI：10.1039/c39730000363

  日期：——

  Addition of dichlorocarbene to 1,4,5,8-tetra-methoxynaphthalene (I) and the tetramethylpurpurogallin (IV) affords the benzocyclo-octatrienediones (III) and (VI) together with the bishomonaphthalene (II) and the benzobishomotropone (V), respectively.

  在1,4,5,8-四甲氧基萘（I）和四甲基紫嘌呤（IV）中加入二氯卡宾可得到苯并环-八碳二烯（III）和（VI）以及双苯并萘（II）和苯并二茂铁酮（V）分别。
• [EN] ANTAGONISTS OF THE TOLL-LIKE RECEPTOR 1/2 COMPLEX<br/>[FR] ANTAGONISTES DU COMPLEXE DE RÉCEPTEUR 1/2 DE TYPE TOLL
  申请人：UNIV COLORADO REGENTS

  公开号：WO2014022287A1

  公开（公告）日：2014-02-06

  Provided are compounds, compositions and methods for treating Toll-like receptor 1/2 complex (TLRI/2) related inflammatory disorders. Small molecules, based on the benzotropolone scaffold, capable of influencing downstream signaling are dislcosed as well as methods of making and modifying these molecules. Also provided are methods for treating a subject for a clinical condition associated with Toll¬ like receptor complex 1/2 activation, comprising administering to the subject an effective amount of a benzotropolone compound.

  提供了用于治疗Toll样受体1/2复合物（TLR1/2）相关炎症性疾病的化合物、组合物和方法。基于苯并三酮骨架的小分子，能够影响下游信号传导，以及制备和修改这些分子的方法也已披露。还提供了用于治疗与Toll样受体复合物1/2激活相关的临床状况的方法，包括向受试者施用有效量的苯并三酮化合物。
• Synthesis and biological evaluation of O-alkylated tropolones and related α-ketohydroxy derivatives as ribonucleotide reductase inhibitors
  作者：I Tamburlin-Thumin

  DOI：10.1016/s0223-5234(01)01249-1

  日期：2001.6

  A series of O-alkylated tropolones and related alpha-ketohydroxy compounds were evaluated for their biological activities and were shown to present an expected ribonucleotide reductase inhibition and cytotoxicity against some cancer cell lines but no antitubulin activity. Pharmacomodulation studies were realised to understand and enhance the observed activities. These original benzylic, heterocyclic

  评估了一系列O-烷基化的对苯二酚和相关的α-酮羟基化合物的生物活性，并显示出它们对某些癌细胞系具有预期的核糖核苷酸还原酶抑制作用和细胞毒性，但没有抗微管蛋白活性。进行药物调节研究以理解和增强观察到的活性。这些原始的苄基，杂环和烯丙基化合物是通过我们实验室开发的相转移催化的O-烷基化反应合成的。
• Synthesis and in vitro anti-protozoal activity of a series of benzotropolone derivatives incorporating endocyclic hydrazines
  作者：Hongyu Ren、Shannon Grady、Matthew Banghart、Jason S Moulthrop、Howard Kendrick、Vanessa Yardley、Simon L Croft、Guillermo Moyna

  DOI：10.1016/j.ejmech.2003.07.004

  日期：2003.11

  The preparation and evaluation as potential anti-protozoal agents of molecules bearing an endocyclic hydrazine moiety is presented. The synthetic route to this new series of compounds is straightforward, involving a hetero Diels-Alder reaction between different benzotropolone esters and diethyl azodicarboxylate (DEAD). While they show limited or no in vitro activity against Leishmania donovani, Plasmodium

  提出了制备和评价作为带有内环肼部分的分子的潜在的抗原生动物剂。合成这一系列新化合物的方法很简单，涉及到不同的苯并马酚酮酯和偶氮二羧酸二乙酯（DEAD）之间的杂Diels-Alder反应。尽管它们显示出对杜氏利什曼原虫，恶性疟原虫和布氏锥虫的体外活性有限或没有体外活性，但是其中一些化合物对15.8-41.0 microM范围的克氏锥虫具有活性。这些活性与苯并硝唑（IC50 6.0 microM）相当，后者是治疗克氏锥虫感染的主要化学疗法。此外，除一种新的双环肼酯外，几乎所有无毒，