1-(2,4-二羟基苯基)-2-(4-羟基苯基)-乙酮 | 17720-60-4

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 中文名称: 1-(2,4-二羟基苯基)-2-(4-羟基苯基)-乙酮
• 中文别名: 2',4'-二羟基-2-(4-羟基苯基苯乙酮)；1-(2,4-二羟基苯基)-2-(4-羟基苯基)乙酮
• 英文名称: 2,4,4'-trihydroxy deoxybenzoin
• 英文别名: 1-(2,4-dihydroxyphenyl)-2-(4-hydroxyphenyl)ethanone；2',4'-dihydroxy-2-(4-hydroxyphenyl)acetophenone
• CAS: 17720-60-4
• 化学式: C₁₄H₁₂O₄
• 分子量: 244.247
• InChiKey: KLFCJXAPIFIIFR-UHFFFAOYSA-N

物化性质

• 熔点：
  192 °C
• 沸点：
  499.0±14.0 °C(Predicted)
• 密度：
  1.380

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2914501900
• 危险性防范说明：
  P261,P280
• 危险性描述：
  H317
• 储存条件：
  室温下，保存于惰性气体中。

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : 1-(2,4-Dihydroxyphenyl)-2-(4-
Hydroxyphenyl)Ethanone
: OTV000030
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.

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Skin sensitisation (Category 1), H317
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
Xi Irritant R43
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)
May cause an allergic skin reaction.
Precautionary statement(s)
Wear protective gloves.
Supplemental Hazard none
Statements
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 : 244,25 g/mol
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
1-(2,4-Dihydroxyphenyl)-2-(4-Hydroxyphenyl)Ethanone
Skin Sens. 1; H317 <= 100 %
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
1-(2,4-Dihydroxyphenyl)-2-(4-Hydroxyphenyl)Ethanone
Xi, R43 <= 100 %
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. 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. Ensure
adequate ventilation. 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 contact with skin and eyes. 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
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
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).
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
Strong oxidizing agents
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
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
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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-(2,4-二羟基苯基)-2-(4-羟基苯基)-乙酮 在 盐酸 、 sodium tetrahydroborate 、 乙醇 、 甲酸铵 、 palladium(II) hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 脑益嗪
  参考文献：
  名称：

  Structure–Activity Relationship of Phytoestrogen Analogs as ERα/β Agonists with Neuroprotective Activities

  摘要：

  一组异黄酮和类黄酮类似物被制备并评估了其对雌激素受体α（ERα）和ERβ的转录激活作用及抗神经炎症活性。对天然存在的植物雌激素及其代谢物和相关异黄酮类似物的结构－活性关系（SAR）研究显示，异黄酮的C环对ER活性和选择性的重要性。对接研究表明，黄酮醇2和脱氢异黄酮8在ERα和ERβ活性位点的假定结合模式，揭示了脱氢异黄酮8的良好活性和选择性。在测试的化合物中，异黄酮7和脱氢异黄酮8是最有效的ERα/β激动剂，具有ERβ选择性和神经保护活性。本研究为进一步开发具有神经保护潜力的强效和选择性ER激动剂提供了关于异黄酮的SAR知识。

  DOI：

  10.1248/cpb.c20-00706
• 作为产物：
  描述：

  对氯苯乙腈 在 盐酸 、 水 、 zinc(II) chloride 作用下， 以 乙醚 为溶剂， 生成 1-(2,4-二羟基苯基)-2-(4-羟基苯基)-乙酮
  参考文献：
  名称：

  异黄酮和异黄酮作为人类12和15脂氧合酶的强抑制剂的体外研究

  摘要：

  在这项研究中，我们研究了16种异黄酮和异黄酮衍生物作为人类脂氧合酶的潜在抑制剂（血小板12-脂氧合酶，网状细胞15-脂氧合酶-1和上皮15-脂氧合酶-2）。类黄酮黄ical素（一种已知的脂加氧酶抑制剂）用作阳性对照。四种化合物，6,7-二羟基-3'-氯异黄酮（1c），7-羟基-8-甲基-4'-氯异黄酮（5a），7,8-二羟基-4'-甲基异黄酮（5b）和7， 8-dihydroxy-3'methylisoflavan（5c）是有效的12-lipoxygenases和15-lipoxygenase-1的抑制剂，IC 50小于10μm，而6,7-dihydroxy-4-4'-nitroisoflavone（1b）是12-脂氧合酶的选择性抑制剂。对三种最佳抑制剂（1b，5b，5c）进行了对接研究，抗氧化剂测定和动力学测量。结果表明，环A中的邻苯二酚基团对于这些化合物的抗氧化性能至关重要，并且可能对

  DOI：

  10.1111/cbdd.12157

文献信息

• Identification of an Orally Bioavailable Chromene-Based Selective Estrogen Receptor Degrader (SERD) That Demonstrates Robust Activity in a Model of Tamoxifen-Resistant Breast Cancer
  作者：Johnny Nagasawa、Steven Govek、Mehmet Kahraman、Andiliy Lai、Celine Bonnefous、Karensa Douglas、John Sensintaffar、Nhin Lu、KyoungJin Lee、Anna Aparicio、Josh Kaufman、Jing Qian、Gang Shao、Rene Prudente、James D. Joseph、Beatrice Darimont、Daniel Brigham、Kate Maheu、Richard Heyman、Peter J. Rix、Jeffrey H. Hager、Nicholas D. Smith

  DOI：10.1021/acs.jmedchem.8b00921

  日期：2018.9.13

  antihormonal agents. However, fulvestrant must be administered by intramuscular injections that limit its efficacy. We describe the optimization of ER-α degradation efficacy of a chromene series of ER modulators resulting in highly potent and efficacious SERDs such as 14n. When examined in a xenograft model of tamoxifen-resistant breast cancer, 14n (ER-α degradation efficacy = 91%) demonstrated robust activity

  大约75％的乳腺癌是雌激素受体α（ER-α）阳性，女性通常最初对他莫昔芬和芳香酶抑制剂等抗激素疗法反应良好，但常常会出现耐药性。Fulvestrant是一种基于类固醇的选择性雌激素受体降解剂（SERD），可拮抗和降解ER-α，并且在抗激素药物治疗的患者中显示出一定的活性。然而，氟维司群必须通过肌内注射来限制其功效。我们描述了色烯系列ER调节剂的ER-α降解功效的优化，可导致高效和高效的SERD，例如14n。在耐他莫昔芬的异种移植模型中检查时，14n（ER-α降解功效= 91％）表现出强劲的活性，而尽管口服量较高，但15克（ER-α降解功效= 82％）基本上没有活性。该结果表明，在MCF-7细胞系中优化ER-α降解功效可导致化合物在源自MCF-7背景的他莫昔芬抗性乳腺癌模型中具有强大的作用。
• [EN] 2-SUBSTITUTED ISOFLAVONOID COMPOUNDS, MEDICAMENTS AND USES<br/>[FR] COMPOSÉS ISOFLAVONOÏDES SUBSTITUÉS EN POSITION 2, MÉDICAMENTS ET UTILISATIONS
  申请人：NOVOGEN RES PTY LTD

  公开号：WO2009003229A1

  公开（公告）日：2009-01-08

  2-Substituted isoflavonoid compounds and pharmaceutical compositions containing same are useful as anti-inflammatory agents and antioxidants and for the treatment of related diseases and conditions.

  2-取代异黄酮化合物和含有这些化合物的药物组合物可用作抗炎剂和抗氧化剂，用于治疗相关疾病和症状。
• An Expedient Synthesis of 2-(ω-Carboxyalkyl)polyhydroxyisoflavones
  作者：Nawaf Al-Maharik、Ilpo Mutikainen、Kristiina Wähälä

  DOI：10.1055/s-2000-6351

  日期：——

  Derivatives of the isoflavones daidzein and genistein, carrying a carboxyalkyl attachment at C-2 were prepared by cyclization of unprotected 2,4,4′-trihydroxy- or 2,4,4′,6-tetrahydroxydeoxybenzoin in the presence of a number of 1,ω-alkanedicarboxylic acid monoester monochlorides, K2CO3 and a phase-transfer catalyst in dry acetone. Hydrolysis under basic conditions of the resulting 2-(ω-alkoxycarbonylalkyl)isoflavones gives the title compounds, useful for developing RIA techniques for the analysis of the parent isoflavones.

  将雌激素大豆黄素和大豆黄苷的衍生物，即在C-2位上带有羧基烷基的大豆黄素和大豆黄苷的制备方法，是通过将未保护的2,4,4'-三羟基或2,4,4',6-四羟基脱氧苯甲酸在含有一系列1,ω-烷二羧酸单酯单氯化物、碳酸钾和相转移催化剂的干燥丙酮中进行环化得到的。在碱性条件下对所得的2-(ω-烷氧羰基烷基)异黄酮进行水解，得到标题化合物，这些化合物对于开发用于分析母体异黄酮的RIA技术非常有用。
• [EN] COMBINATIONS OF BENZOPYRAN COMPOUNDS, COMPOSITIONS AND USES THEREOF<br/>[FR] COMBINAISONS DE COMPOSÉS BENZOPYRANE, LEURS COMPOSITIONS ET UTILISATIONS
  申请人：OLEMA PHARMACEUTICALS INC

  公开号：WO2014203129A1

  公开（公告）日：2014-12-24

  This invention relates to a method of treating a disorder modulated, mediated or affected by the estrogen receptor in a subject comprising administering to the subject a specific benzopyran (in the form of a mixture of S-C2 and R-C2 diastereomers or its pure S-diastereomer) in combination with an agent selected from the group consisting of an mTOR inhibitor, a CDK 4/6 inhibitor, a PI3 Kinase inhibitor, a taxane, an antimetabolite, and an antitumor antibiotic.

  本发明涉及一种治疗受雌激素受体调控、介导或影响的疾病的方法，包括向受试者施用一种特定的苯并吡喃（以S-C2和R-C2对映异构体的混合物或其纯S-对映异构体形式）与所选药剂（包括mTOR抑制剂、CDK 4/6抑制剂、PI3激酶抑制剂、紫杉醇、抗代谢物和抗肿瘤抗生素）的组合。
• A Direct Synthesis of 2‐(ω‐Carboxyalkyl)isoflavones from <i>ortho</i> ‐Hydroxylated Deoxybenzoins
  作者：Galyna P. Mrug、Bohdan A. Demydchuk、Svitlana P. Bondarenko、Vitaliy M. Sviripa、Przemyslaw Wyrebek、James L. Mohler、Michael V. Fiandalo、Chunming Liu、Mykhaylo S. Frasinyuk、David S. Watt

  DOI：10.1002/ejoc.201801171

  日期：2018.10.24

  The base‐catalyzed chromone ring‐closure reaction was developed for one‐step synthesis of various 2‐(ω‐carboxyalkyl)isoflavones bearing electron‐donating and electron‐withdrawing groups.

  开发了碱催化的色酮闭环反应，用于一步合成具有供电子基团和吸电子基团的各种2-（ω-羧基烷基）异黄酮。

表征谱图