黄酮 | 525-82-6

• 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: 黄酮
• 中文别名: 2-苯基-4H-1-苯并吡喃-4-酮（黄酮）；2-苯基苯并对氧杂芑酮；黄色素母酮；2-苯基-4H-1-苯并吡喃-4-酮；2-苯基1,4-吡喃酮；2-苯基苯并对吡喃酮；2-苯基-4H-1-苯并吡喃-4-酮(黄酮)；纯化微粒化黄酮成份
• 英文名称: FLAVONE
• 英文别名: 2-phenyl-4H-chromen-4-one；2-phenylchromen-4-one
• CAS: 525-82-6
• 化学式: C₁₅H₁₀O₂
• mdl: MFCD00006825
• 分子量: 222.243
• InChiKey: VHBFFQKBGNRLFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  94-97 °C (lit.)
• 沸点：
  185 °C / 1mmHg
• 密度：
  1.1404 (rough estimate)
• 溶解度：
  >38.3 mg/mL，乙醇溶液； >52.3 mg/mL，溶于 DMSO
• LogP：
  3.560
• 物理描述：
  Solid
• 碰撞截面：
  146.7 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]
• 保留指数：
  2148;2150;2160
• 稳定性/保质期：
  按规格使用和贮存，不会发生分解。避免与氧化物接触。

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

ADMET

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• TSCA：
  Yes
• 危险品标志：
  Xi
• 安全说明：
  S26,S36
• 危险类别码：
  R36/37/38
• WGK Germany：
  2
• RTECS号：
  DJ3100630
• 海关编码：
  2932999099
• 储存条件：
  储存于阴凉、干燥、通风良好的库房。远离火种和热源，避免阳光直射，并确保包装密封。应与酸类及食用化学品分开存放，切忌混储。储区应备有合适的材料以收容泄漏物。

SDS

Name:	Flavone 99+% (TLC) Material Safety Data Sheet
Synonym:	2-Phenyl-4H-1-Benzopyran-4-One; 2-Phenylchromone
CAS:	525-82-6

Section 1 - Chemical Product MSDS Name:Flavone 99+% (TLC) Material Safety Data Sheet
Synonym:2-Phenyl-4H-1-Benzopyran-4-One; 2-Phenylchromone

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
525-82-6	Flavone	>99	208-383-8

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

---

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

---

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use agent most appropriate to extinguish fire. Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Clean up spills immediately, observing precautions in the Protective Equipment section. Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 525-82-6: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 97.00 - 98.50 deg C
Autoignition Temperature: Not applicable.
Flash Point: Not applicable.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: practically insoluble in water
Specific Gravity/Density:
Molecular Formula: C15H10O2
Molecular Weight: 222.24

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 525-82-6: DJ3100630 LD50/LC50:
CAS# 525-82-6: Oral, mouse: LD50 = 2500 mg/kg.
Carcinogenicity:
Flavone - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 525-82-6: No information available.
Canada
CAS# 525-82-6 is listed on Canada's NDSL List.
CAS# 525-82-6 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 525-82-6 is listed on the TSCA inventory.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

简介

黄酮广泛存在于自然界中的某些植物和浆果中，许多中药也含有其成分。科学家发现具有活化石之称的银杏树中含有相对较多的黄酮，可以从银杏叶中提取黄酮。黄酮具有抗炎特性，在体内还能够阻止病原性微生物的生长繁殖。

作用

黄酮可以改善血液循环、降低胆固醇，并含有一种PAF抗凝因子，大大降低了心脑血管疾病的发病率；还可以改善心脑血管疾病的症状，对血压、血糖和血脂有调节作用。此外，黄酮解酒护肝、预防骨质疏松、提高免疫力，并有效治疗便秘。

黄酮还具有神奇的降血糖功效，更重要的是它能稳定胶原质，因此对于糖尿病引起的视网膜病及毛细血管脆化有很好的疗效。

黄酮能够抑制炎性生物酶的渗出，促进伤口愈合和止痛。栎素由于其强抗组织胺性，可以用于治疗各种过敏症。

代谢

黄酮进入肠道后可与肠道菌群相互作用，被代谢为芳香酸或酚酸，或者与肠道上皮细胞结合。例如，槲皮素可以阻止体内某些微生物如瘤胃球菌属和乳酸菌属的生长繁殖。当然，黄酮也可以促进特定菌群的增长，如苹果中的黄酮能增加双歧杆菌属的数量而减少乳酸菌属。

黄酮作用于肠道内容物时，可保护肠道上皮细胞免受药物和食物毒素的侵害，调节脂类和碳水化合物吸收代谢相关的酶活性，并维持肠道屏障完整性。此外，它还能调节肠道激素分泌，调整胃肠道免疫系统，发挥潜在的抗癌作用。

生物活性

黄酮是一种内源性代谢产物。

反应信息

• 作为反应物：
  描述：

  黄酮 在 2,3,4,5,6-五氟苯乙烯 、 二甲基苯基硅烷 、 bis(pentafluorophenyl)borane 、 三氟乙酸 作用下， 以 甲苯 为溶剂， 反应 15.17h， 以80%的产率得到黄烷酮
  参考文献：
  名称：

  硼烷催化的色酮和黄酮的无金属氢化硅烷化

  摘要：

  首次成功实现了色酮和黄酮的 Piers 型氢化硅烷化，使用 0.1 mol% 的硼烷催化剂通过五氟苯乙烯与 HB(C6F5)2 的硼氢化反应原位生成，得到 60-99% 的各种色酮和黄烷酮产量。尝试用手性二炔和 HB(C6F5)2 进行不对称转化，以高产率得到色满酮和黄烷酮，ee 高达 32%。

  DOI：

  10.1055/s-0036-1588474
• 作为产物：
  描述：

  2-(benzoyloxy)-benzoylmethyltriphenylphosphonium bromide 在 三乙胺 作用下， 以 水 为溶剂， 反应 0.58h， 以86%的产率得到黄酮
  参考文献：
  名称：

  分子内光化学Wittig反应在水中合成黄酮和吡喃黄酮

  摘要：

  朝向黄酮和pyranoflavone的合成的新的合成方法已被开发通过光诱导的分子内光化学维悌希反应在水到芳氧基羰基和适当取代的鏻溴化物SANS任何相转移催化剂或助催化剂。

  DOI：

  10.1016/j.tetlet.2011.10.134
• 作为试剂：
  描述：

  5,5-二甲基-1-吡咯啉-N-氧化物 在 黄酮 、 双氧水 作用下， 以 水 、 丙酮 为溶剂， 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Hydroxyl radical scavenging activity of flavonoids

  摘要：

  DOI：

  10.1016/s0031-9422(00)83860-1

文献信息

• [EN] COMPOUNDS AND COMPOSITIONS COMPRISING CDK INHIBITORS AND METHODS FOR THE TREATMENT OF CANCER<br/>[FR] COMPOSÉS ET COMPOSITIONS COMPRENANT DES INHIBITEURS DES CDK ET MÉTHODES DE TRAITEMENT DU CANCER
  申请人：UNIV GEORGIA STATE RES FOUND

  公开号：WO2010129858A1

  公开（公告）日：2010-11-11

  Disclosed herein are compounds suitable for use as antitumor agents, methods for treating cancer wherein the disclosed compounds are used in making a medicament for the treatment of cancer, methods for treating a tumor comprising, administering to a subject a composition comprising one or more of the disclosed cytotoxic agents, and methods for preparing the disclosed antitumor agents.

  本文披露了适用作抗肿瘤药剂的化合物，用于治疗癌症的方法，其中所披露的化合物用于制备治疗癌症的药物，治疗肿瘤的方法包括向受试者施用包含一种或多种所披露的细胞毒性药剂的组合物，以及制备所披露的抗肿瘤药剂的方法。
• [EN] SYNTHETIC ANALOGUES OF XANTHOHUMOL<br/>[FR] ANALOGUES SYNTHÉTIQUES DU XANTHOHUMOL
  申请人：UNIV PISA

  公开号：WO2014167481A1

  公开（公告）日：2014-10-16

  The present invention relates to novel synthetic analogues of xanthohumol and the use thereof.

  本发明涉及新型黄葛素合成类似物及其用途。
• Novel and Efficient Synthesis of Iminocoumarins via Copper-Catalyzed Multicomponent Reaction
  作者：Sun-Liang Cui、Xu-Feng Lin、Yan-Guang Wang

  DOI：10.1021/ol061685w

  日期：2006.9.1

  A variety of substituted iminocoumarins are prepared in good to excellent yields via a copper-catalyzed multicomponenet reaction of sulfonyl azides, terminal alkynes, and salicylaldehydes or o-hydroxylacetophenones. The method is general, mild, versatile, and efficient. A plausible mechanism for the domino process is proposed.

  通过铜催化的磺酰叠氮化物，末端炔烃，水杨醛或邻羟基内苯乙酮的多组分反应，可以制备出高至优收率的各种取代的亚氨基香豆素。该方法是通用，温和，通用和高效的。提出了一种可行的多米诺骨牌机制。
• [EN] PROCESS FOR SYNTHESIS OF OROXYLIN A<br/>[FR] PROCÉDÉ DE SYNTHÈSE D'OROXYLINE A
  申请人：MAJEED MUHAMMED

  公开号：WO2020032913A1

  公开（公告）日：2020-02-13

  Disclosed is a novel, simple, scalable and environment friendly process for the synthesis of Oroxylin A from Baicalin. Baicalm is esterified to obtain a methyl ester which is further selectively methylated to provide Oroxylin A gluciironide methyl ester which on de- glycosylation results in the formation of Oroxylin A.

  揭示了一种新颖、简单、可扩展且环境友好的过程，用于从黄芩苷合成黄芩素A。将黄芩苷酯化以获得甲酯，进一步选择性地甲基化以提供黄芩素A葡糖苷甲酯，脱糖后形成黄芩素A。
• [EN] 7-CARBOXYMETHYLOXY-3', 4', 5-TRIMETHOXY FLAVONE MONOHYDRATE, THE PREPARATION METHOD AND USES THEREOF<br/>[FR] MONOHYDRATE DE 7-CARBOXYMETHYLOXY-3',4',5-TRIMETHOXY FLAVONE, SON PROCEDE DE PREPARATION ET SON UTILISATION
  申请人：DONG A PHARM CO LTD

  公开号：WO2005023244A1

  公开（公告）日：2005-03-17

  The present invention relates to 7-carboxymethyloxy-3’, 4’, 5-trimethoxy flavone.monohydrate which is a non hygroscopic product suitable for the preparation of metered dose of 7-carboxymethyloxy-3’, 4’, 5-trimethoxy flavone having protective activity for gastrointestinal tract including the colon, and a preparation method and uses thereof. 7-carboxymethyloxy-3’, 4’, 5-trimethoxy flavone.monohydrate of the present invention has advantages such as mucus protecting activity for gastrointestinal tract including the colon, convenience for handling and storage under ordinary humidity owing to its non-hygroscopicity, and ability to contain an active compound consistently for the formulation production of a medicine. In addition, the preparation method of 7-carboxymethyloxy-3’, 4’, 5-trimethoxy flavone.monohydrate of the present invention reduces long steps of total synthesis and requires mild conditions for the production of a compound because autoclave condition is not necessary for methylation in this case, and makes mass-production possible without any purification process such as recrystallization or column chromatography.

  本发明涉及7-羧甲氧基-3'，4'，5-三甲氧基黄酮一水合物，这是一种非吸湿性产品，适用于制备具有对胃肠道包括结肠具有保护活性的7-羧甲氧基-3'，4'，5-三甲氧基黄酮的定量剂量，以及其制备方法和用途。本发明的7-羧甲氧基-3'，4'，5-三甲氧基黄酮一水合物具有诸如对胃肠道包括结肠的黏膜保护活性、由于其非吸湿性而在普通湿度下方便处理和储存的优点，以及能够持续包含活性化合物以便制剂生产药物。此外，本发明的7-羧甲氧基-3'，4'，5-三甲氧基黄酮一水合物的制备方法减少了总合成的长步骤，并且在这种情况下，对于甲基化不需要高压灭菌条件，因此在生产化合物时需要温和条件，并且可以实现无需任何纯化过程（如重结晶或柱层析）的大规模生产。

表征谱图