汉黄芩素 | 632-85-9

• 物质功能分类: 原料药 - 循环系统用药 - 抗高血压病药
• 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: 汉黄芩素
• 中文别名: 5,7-二羟基-8-甲氧基-2-苯基-4H-1-苯并呋喃-4-酮；汉黄芩黄酮
• 英文名称: wogonin
• 英文别名: 5,7-dihydroxy-8-methoxyflavone；5,7-dihydroxy-8-methoxy-2-phenyl-4H-chromen-4-one；5,7-dihydroxy-8-methoxy-2-phenylchromen-4-one
• CAS: 632-85-9
• 化学式: C₁₆H₁₂O₅
• mdl: MFCD00017736
• 分子量: 284.268
• InChiKey: XLTFNNCXVBYBSX-UHFFFAOYSA-N

物化性质

• 熔点：
  203-206°C
• 沸点：
  518.8±50.0 °C(Predicted)
• 密度：
  1.420±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜：≥20mg/mL
• 最大波长(λmax)：
  319nm(EtOH)(lit.)
• LogP：
  2.140 (est)
• 稳定性/保质期：
  远离氧化物、光和热。

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.062
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

ADMET

代谢

汉黄芩素已知的人类代谢物包括(2S,3S,4S,5R)-3,4,5-三羟基-6-(5-羟基-8-甲氧基-4-氧代-2-苯基色烯-7-基)氧杂环己烷-2-羧酸。

Wogonin has known human metabolites that include (2S,3S,4S,5R)-3,4,5-trihydroxy-6-(5-hydroxy-8-methoxy-4-oxo-2-phenylchromen-7-yl)oxyoxane-2-carboxylic acid.

来源:NORMAN Suspect List Exchange

安全信息

• 安全说明：
  S24/25,S26,S36/37/39,S45
• WGK Germany：
  3
• 海关编码：
  29329990
• RTECS号：
  SJ8922500
• 危险类别：
  8
• 危险类别码：
  R20/21/22,R36/37/38
• 包装等级：
  III
• 危险品运输编号：
  3145
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  存放在密封容器中，并置于阴凉、干燥处，于2-10℃避光保存。储存地点需远离氧化剂。

SDS

---

SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Wogonin hydrate
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. : 632-85-9
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
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
The product does not need to be labelled in accordance with EC directives or respective national laws.
Other hazards - none

---

SECTION 3: Composition/information on ingredients
Substances
Synonyms : 5,7-Dihydroxy-8-methoxyflavone
Formula : C16H12O5 · xH2O
Molecular Weight : 284,26 g/mol
CAS-No. : 632-85-9
No components need to be disclosed according to the applicable regulations.

---

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
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
Avoid dust formation. Avoid breathing vapours, mist or gas.
For personal protection see section 8.
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.

---

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.
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.
Recommended storage temperature: 2 - 8 °C
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
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).
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) 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- 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
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: LK8331000
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
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.

---

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

---

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
For this product a chemical safety assessment was not carried out

---

SECTION 16: Other information
Further information
Copyright 2013 Co. LLC. License granted to make unlimited paper copies for internal use
only.
The above information is believed to be correct but does not purport to be all inclusive and shall be
used only as a guide. The information in this document is based on the present state of our knowledge
and is applicable to the product with regard to appropriate safety precautions. It does not represent any
guarantee of the properties of the product. Corporation and its Affiliates shall not be held
liable for any damage resulting from handling or from contact with the above product. See
and/or the reverse side of invoice or packing slip for additional terms and conditions of sale.

制备方法与用途

理化性质

黄芩的黄色针状结晶（乙醇水溶液或醋酸乙酯-苯），熔点203℃，极易溶于甲醇、乙醇、丙酮和醋酸乙酯，溶于乙醇、醋酸和氯仿，微溶于苯和水，不溶于二硫化碳和石油醚。

黄芩

黄芩为唇形科黄芩属植物黄芩（Scutellaria baicalensis Georgi）的干燥根。主要生长在草原及高燥砾质山坡，分布于我国的河北、内蒙古、山西、山东和陕西等地。

植物形态

多年生草本。主根粗壮，略呈圆锥状，外皮褐色；茎方形，四面有棱角；叶对生，卵形至披针形，边缘有锯齿；花小，聚集成顶生的穗状花序。

化学成分

含有多种黄酮类化合物，其中以汉黄芩素最为重要。汉黄芩素极易溶于甲醇、乙醇、丙酮和醋酸乙酯，溶于乙醇、醋酸和氯仿，微溶于苯和水，不溶于二硫化碳和石油醚。

提取方法

1. 水蒸汽蒸馏法
2. 有机溶剂萃取法
3. 索氏提取法
4. 酶提取法
5. 超声提取法

药理作用

• 解痉作用：黄芩具有显著的平滑肌松弛效果，可用于治疗各种消化道、呼吸道及血管平滑肌痉挛。
• 抗癌作用：研究表明，汉黄芩素等成分对多种癌细胞有抑制作用，显示出一定的抗癌潜力。
• 利尿作用：能促进尿液分泌，有助于消除体内多余的水分和盐分，适用于水肿、高血压等症状的辅助治疗。

鉴别方法

采用高效液相色谱法（HPLC）测定汉黄芩素的含量。具体条件如下：

• 分离成分：汉黄芩素
• 色谱柱固定相：Nova-Pak C18 5 μm (4.5 mmＸ150 mm)
• 流动相：水-乙腈-冰醋酸（73:23:3）
• 流速：1.0 ml/min
• 检测波长：257 nm
• 柱温：25℃

用途

黄芩及其提取物广泛应用于中药含量测定、鉴定和药理实验中。同时，汉黄芩素因其多种生物活性，在解痉、抗癌及利尿等方面显示出巨大潜力。

反应信息

• 作为反应物：
  描述：

  汉黄芩素 在 三氯氧磷 、 水 作用下， 以 乙腈 为溶剂， 反应 7.0h， 以0.63 g的产率得到(8-Methoxy-4-oxo-2-phenyl-5-phosphonooxychromen-7-yl) dihydrogen phosphate
  参考文献：
  名称：

  用于治疗的汉黄芩素衍生物

  摘要：

  本发明提供汉黄芩素的衍生物及其制备方法和用途，汉黄芩素的衍生物是通过对其结构的羟基基团进行化学修饰所得，所涉及的汉黄芩素的衍生物可以在药物组合物中使用，用于生产治疗乙肝及白血病治疗用的药物。

  公开号：

  CN102516301B
• 作为产物：
  描述：

  7-Benzyloxy-5,8-dihydroxy-flavon 在 palladium on activated charcoal 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 汉黄芩素
  参考文献：
  名称：

  过渡金属催化的 C-H 键氧化对黄酮类化合物的区域选择性羟基化

  摘要：

  5,6,7-三羟基和 5,7,8-三羟基黄酮的区域选择性合成是通过过渡金属催化的 C-H 氧化作为使用天然富集的 5,7-二羟基黄酮的关键步骤实现的。已开发的化学方法用于合成天然存在且具有生物活性的类黄酮汉黄芩素 ( 2 )、oroxylin A ( 3 ) 及其糖基化衍生物（4和5），作为潜在的肉碱棕榈酰转移酶 1 激活剂。

  DOI：

  10.1021/acs.orglett.3c00517
• 作为试剂：
  描述：

  silver nitrate 在 汉黄芩素 作用下， 生成 silver
  参考文献：
  名称：

  Combination Effect of Silver Nanoparticles and Histone Deacetylases Inhibitor in Human Alveolar Basal Epithelial Cells

  摘要：

  虽然已经报告了许多治疗肺部疾病的策略，但使用银纳米颗粒（AgNPs）和组蛋白去乙酰化酶抑制剂（HDACi）的联合治疗机制仍不清楚。因此，创新的治疗策略对于解决这种高度侵袭性肺癌的治疗挑战至关重要。AgNPs和HDACi似乎是最佳的抗癌治疗候选者，因为它们在各种癌细胞中具有抗增殖作用。首先，我们使用黄芩素作为还原和稳定剂合成了AgNPs，随后通过各种分析技术对合成的AgNPs进行了表征。合成的AgNPs对A549细胞表现出剂量和大小依赖性毒性。有趣的是，AgNPs和MS-275的组合显著诱导凋亡，伴随着反应性氧化物（ROS）水平的增加；乳酸脱氢酶（LDH）泄漏；TNFα分泌；线粒体功能障碍；自噬体积累；caspase 9/3激活；分别上调和下调促凋亡基因和抗凋亡基因；最终诱导DNA断裂。我们的研究结果表明，AgNPs和MS-275通过线粒体介导的内源性凋亡途径诱导A549肺细胞死亡。最后，我们的数据显示，AgNPs和MS-275的组合是治疗肺癌的一种有前途的新方法，我们的研究结果有助于理解AgNPs和MS-275在肺部疾病中的潜在作用。然而，需要进一步研究以增强这种联合治疗在癌症治疗试验中的使用。

  DOI：

  10.3390/molecules23082046

文献信息

• [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] COMPOUNDS FOR THE TREATMENT OF HEPATITIS B VIRUS INFECTION<br/>[FR] COMPOSÉS POUR LE TRAITEMENT D'UNE INFECTION PAR LE VIRUS DE L'HÉPATITE B
  申请人：GILEAD SCIENCES INC

  公开号：WO2017205115A1

  公开（公告）日：2017-11-30

  The present disclosure generally relates to compounds and pharmaceutical compositions which may be used in methods of treating a hepatitis B virus infection.

  本公开涉及一般与化合物和药物组合物有关，这些化合物和药物组合物可用于治疗乙型肝炎病毒感染的方法。
• Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches
  作者：Baojian Wu、Xiaoqiang Wang、Shuxing Zhang、Ming Hu

  DOI：10.1007/s11095-012-0666-z

  日期：2012.6

  Catalytic selectivity of human UGT1A9, an important membrane-bound enzyme catalyzing glucuronidation of xenobiotics, was determined experimentally using 145 phenolics and analyzed by 3D-QSAR methods. Catalytic efficiency of UGT1A9 was determined by kinetic profiling. Quantitative structure activity relationships were analyzed using CoMFA and CoMSIA techniques. Molecular alignment of substrate structures was made by superimposing the glucuronidation site and its adjacent aromatic ring to achieve maximal steric overlap. For a substrate with multiple active glucuronidation sites, each site was considered a separate substrate. 3D-QSAR analyses produced statistically reliable models with good predictive power (CoMFA: q2 = 0.548, r2 = 0.949, r pred 2  = 0.775; CoMSIA: q2 = 0.579, r2 = 0.876, r pred 2  = 0.700). Contour coefficient maps were applied to elucidate structural features among substrates that are responsible for selectivity differences. Contour coefficient maps were overlaid in the catalytic pocket of a homology model of UGT1A9, enabling identification of the UGT1A9 catalytic pocket with a high degree of confidence. CoMFA/CoMSIA models can predict substrate selectivity and in vitro clearance of UGT1A9. Our findings also provide a possible molecular basis for understanding UGT1A9 functions and substrate selectivity.

  通过实验使用145种酚类化合物，并通过3D-QSAR方法分析，确定了人UGT1A9的催化选择性。UGT1A9是一种重要的膜结合酶，催化外源性物质的葡糖醛酸化反应。通过动力学分析确定了UGT1A9的催化效率。使用CoMFA和CoMSIA技术分析了定量结构活性关系。通过将葡糖醛酸化位点及其相邻的芳香环重叠，实现了底物结构的最大立体重叠。对于具有多个活性葡糖醛酸化位点的底物，每个位点被视为单独的底物。3D-QSAR分析产生了统计上可靠的模型，具有良好的预测能力（CoMFA：q2=0.548，r2=0.949，r pred 2=0.775；CoMSIA：q2=0.579，r2=0.876，r pred 2=0.700）。通过轮廓系数图阐明了底物中负责选择性差异的结构特征。将轮廓系数图叠加在UGT1A9的同源模型的催化口袋中，能够高度自信地识别UGT1A9的催化口袋。CoMFA/CoMSIA模型可以预测底物的选择性和UGT1A9的体外清除率。我们的发现还提供了理解UGT1A9功能和底物选择性的可能分子基础。
• [EN] COMBINATION OF HEPATITIS B VIRUS (HBV) VACCINES AND PYRIDOPYRIMIDINE DERIVATIVES<br/>[FR] ASSOCIATION DE VACCINS CONTRE LE VIRUS DE L'HÉPATITE B (VHB) ET DE DÉRIVÉS DE PYRIDOPYRIMIDINE
  申请人：JANSSEN SCIENCES IRELAND UNLIMITED CO

  公开号：WO2020255038A1

  公开（公告）日：2020-12-24

  Therapeutic combinations of hepatitis B virus (HBV) vaccines and a pyridopyrimidine derivative are described. Methods of inducing an immune response against HBV or treating an HBV-induced disease, particularly in individuals having chronic HBV infection, using the disclosed therapeutic combinations are also described. The invention provides therapeutic combinations or compositions and methods for inducing an immune response against hepatitis B viruses (HBV) infection.

  本发明描述了乙型肝炎病毒（HBV）疫苗和吡啶吡嘧啶衍生物的治疗组合。还描述了利用所述治疗组合诱导免疫应答对抗HBV或治疗HBV引起的疾病的方法，特别是在患有慢性HBV感染的个体中。该发明提供了用于诱导免疫应答对抗乙型肝炎病毒（HBV）感染的治疗组合或组成物和方法。
• [EN] ANTICANCER AGENTS<br/>[FR] AGENTS ANTICANCÉREUX
  申请人：YISSUM RES DEV CO OF HEBREW UNIV JERUSALEM LTD

  公开号：WO2021024256A1

  公开（公告）日：2021-02-11

  The invention generally concerns a method for conjugating an active material to a Pt complex.

  这项发明通常涉及一种将活性材料与铂配合物结合的方法。

表征谱图