穗花杉双黄酮 | 1617-53-4

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: 穗花杉双黄酮
• 中文别名: 阿曼托黄酮
• 英文名称: amentoflavone
• 英文别名: 8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• CAS: 1617-53-4
• 化学式: C₃₀H₁₈O₁₀
• mdl: MFCD00017470
• 分子量: 538.467
• InChiKey: YUSWMAULDXZHPY-UHFFFAOYSA-N

物化性质

• 熔点：
  >300°C (dec.)
• 沸点：
  910.5±65.0 °C(Predicted)
• 密度：
  1.656±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（轻微）、甲醇（轻微、加热）、吡啶（轻微）
• LogP：
  3.492 (est)
• 物理描述：
  Solid
• 碰撞截面：
  230.16 Ų [M+H]+ [CCS Type: DT, Method: stepped-field]

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  40
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  174
• 氢给体数：
  6
• 氢受体数：
  10

安全信息

• 安全说明：
  S22,S24/25
• WGK Germany：
  3
• 海关编码：
  29329990
• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

SDS

Amentoflavone Revision number: 5
SAFETY DATA SHEET

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Section 1. IDENTIFICATION
Product name: Amentoflavone

Revision number: 5

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Section 2. HAZARDS IDENTIFICATION
GHS classification
PHYSICAL HAZARDS Not classified
Not classified
HEALTH HAZARDS
ENVIRONMENTAL HAZARDS Not classified
GHS label elements, including precautionary statements
Pictograms or hazard symbols None
No signal word
Signal word
Hazard statements None
None
Precautionary statements:

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substance/mixture: Substance
Components: Amentoflavone
Percent: >98.0%(LC)
CAS Number: 1617-53-4
Chemical Formula: C30H18O10

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Section 4. FIRST AID MEASURES
Inhalation: Remove victim to fresh air and keep at rest in a position comfortable for breathing.
Get medical advice/attention if you feel unwell.
Skin contact: Remove/Take off immediately all contaminated clothing. Rinse skin with
water/shower. If skin irritation or rash occurs: Get medical advice/attention.
Eye contact: Rinse cautiously with water for several minutes. Remove contact lenses, if present
and easy to do. Continue rinsing. If eye irritation persists: Get medical
advice/attention.
Ingestion: Get medical advice/attention if you feel unwell. Rinse mouth.
A rescuer should wear personal protective equipment, such as rubber gloves and air-
Protection of first-aiders:
tight goggles.

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Section 5. FIRE-FIGHTING MEASURES
Suitable extinguishing Dry chemical, foam, water spray, carbon dioxide.
media:
Precautions for firefighters: Fire-extinguishing work is done from the windward and the suitable fire-extinguishing
method according to the surrounding situation is used. Uninvolved persons should
evacuate to a safe place. In case of fire in the surroundings: Remove movable
containers if safe to do so.
Amentoflavone

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Section 5. FIRE-FIGHTING MEASURES
Special protective When extinguishing fire, be sure to wear personal protective equipment.
equipment for firefighters:

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Section 6. ACCIDENTAL RELEASE MEASURES
Personal precautions, Use personal protective equipment. Keep people away from and upwind of spill/leak.
protective equipment and Entry to non-involved personnel should be controlled around the leakage area by
emergency procedures: roping off, etc.
Environmental precautions: Prevent product from entering drains.
Methods and materials for Sweep dust to collect it into an airtight container, taking care not to disperse it.
containment and cleaning Adhered or collected material should be promptly disposed of, in accordance with
up: appropriate laws and regulations.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Handling is performed in a well ventilated place. Wear suitable protective equipment.
Technical measures:
Prevent dispersion of dust. Wash hands and face thoroughly after handling.
Use a local exhaust if dust or aerosol will be generated.
Advice on safe handling: Avoid contact with skin, eyes and clothing.
Conditions for safe storage, including any
incompatibilities
Keep container tightly closed. Store in a refrigerator.
Storage conditions:
Store away from incompatible materials such as oxidizing agents.
Heat-sensitive
Packaging material: Comply with laws.

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Section 8. EXPOSURE CONTROLS / PERSONAL PROTECTION
Engineering controls: Install a closed system or local exhaust as possible so that workers should not be
exposed directly. Also install safety shower and eye bath.
Personal protective equipment
Respiratory protection: Dust respirator. Follow local and national regulations.
Hand protection: Protective gloves.
Eye protection: Safety glasses. A face-shield, if the situation requires.
Skin and body protection: Protective clothing. Protective boots, if the situation requires.

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Section 9. PHYSICAL AND CHEMICAL PROPERTIES
Solid
Physical state (20°C):
Form: Crystal- Powder
Colour: White - Pale yellow green
Odour: No data available
pH: No data available
Melting point/freezing point:No data available
Boiling point/range: No data available
No data available
Flash point:
Flammability or explosive
limits:
Lower: No data available
No data available
Upper:
Relative density: No data available
Solubility(ies):
[Water] No data available
[Other solvents] No data available

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Section 10. STABILITY AND REACTIVITY
Chemical stability: Stable under proper conditions.
Possibility of hazardous No special reactivity has been reported.
reactions:
Amentoflavone

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Section 10. STABILITY AND REACTIVITY
Incompatible materials: Oxidizing agents
Hazardous decomposition Carbon monoxide, Carbon dioxide
products:

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Section 11. TOXICOLOGICAL INFORMATION
Acute Toxicity: No data available
Skin corrosion/irritation: No data available
Serious eye No data available
damage/irritation:
Germ cell mutagenicity: No data available
Carcinogenicity:
IARC = No data available
NTP = No data available
Reproductive toxicity: No data available

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Section 12. ECOLOGICAL INFORMATION
Ecotoxicity:
Fish: No data available
No data available
Crustacea:
Algae: No data available
Persistence / degradability: No data available
Bioaccumulative No data available
potential(BCF):
Mobility in soil
No data available
Log Pow:
Soil adsorption (Koc): No data available
No data available
Henry's Law
constant(PaM3/mol):

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Section 13. DISPOSAL CONSIDERATIONS
Recycle to process, if possible. Consult your local regional authorities. You may be able to dissolve or mix material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber system.
Observe all federal, state and local regulations when disposing of the substance.

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Section 14. TRANSPORT INFORMATION
Does not correspond to the classification standard of the United Nations
Hazards Class:
UN-No: Not listed

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Section 15. REGULATORY INFORMATION
Safe management ordinance of dangerous chemical product (State Council announces on January 26, 2002
and revised on February 16,2011): Safe use and production, the storage of a dangerous chemical, transport,
loading and unloading were prescribed.
Amentoflavone

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

穗花杉双黄酮具有多种生物活性，包括抗炎、抗氧化、抗病毒、抗胖瘤、降血糖和扩张血管等作用。它是一种环氧化酶（COX）和黄嘌呤氧化酶抑制剂，同时也是蝶酸醋酶抑制剂。其体外对柯萨奇病毒和泡疹病毒型有良好抑制效果。

穗花杉双黄酮 (Amentoflavone) 是一种天然的双黄酮类化合物，具有抗炎、抗氧化及神经保护等多种生物活性。它是一种黄色结晶粉末，易溶于甲醇，几乎不溶于乙醚，来源于卷柏和杉木枝叶。

这种化合物在肿瘤治疗方面表现出显著效果，能够清除自由基、舒张血管以及降血糖。研究表明，Amentoflavone 能抑制诱导的内皮型一氧化氮合酶（INOS）表达，并阻断 LPS 诱导的 NF-κB p50 活化及 p65 的转位和 IKKα 的降解，在巨噬细胞中发挥抗炎作用。此外，它还能上调 PPAR-γ 并抑制 COX-2 的诱导。Amentoflavone 还是一种 GABAA 受体的负调节剂，能够阻断苯二氮卓类药物结合位点。在体外实验中，该化合物对呼吸道合胞病毒 (RSV) 具有抗病毒活性，IC50 为 5.5 μg/ml，并且在体外对苯二氮卓受体的抑制作用 IC50 值为 14.9 ± 1.9 nM。

反应信息

• 作为反应物：
  描述：

  穗花杉双黄酮 在 氢溴酸 作用下， 生成 罗波斯塔双黄酮
  参考文献：
  名称：

  13C NMR studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids

  摘要：

  DOI：

  10.1016/s0031-9422(00)82499-1
• 作为产物：
  描述：

  四氢阿曼托黄素; 穗花杉双黄酮 在 硫酸 、 碘 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 生成 穗花杉双黄酮
  参考文献：
  名称：

  Tetrahydroamentoflavone from nuts of Semecarpus prainii

  摘要：

  DOI：

  10.1016/0031-9422(81)83061-0

文献信息

• Synthesis of C-3 Coupled Biflavonoids and C-3 Coupled Biflavonoid Analogues
  申请人：Van Der Westhuizen Jan Hendrik

  公开号：US20120289715A1

  公开（公告）日：2012-11-15

  The invention relates to methods for the preparation of an optically inactive and optically active compounds which are selected from the group consisting of C-3 coupled biflavonoids and C-3 coupled biflavonoid analogues from a starting material or intermediate which are respectively selected from the group consisting of optically inactive or optically active flavan-3-ols and optically active flavan-3-ones, the method comprising the steps of (a) providing an optically inactive or active compound having a flavan-3-ol structure or a compound which is a flavan-3-one, (b) if a compound having a flavan-3-ol structure with a hydroxy group on the C-3 carbon is selected as starting material, converting the hydroxy group on the C-3 carbon of the compound having the flavan-3-ol structure to an oxo group to form a flavan-3-one of that compound, (c) providing a compound having a nucleophilic aromatic moiety, which compound is selected from the group of compounds having a nucleophilic aromatic moiety and which have flavonoid base structures and compounds having a nucleophilic aromatic moiety and which do not have a flavonoid base structure, (d) contacting the flavan-3-one provided by step (a) or obtained by step (b) with the compound containing the nucleophilic aromatic moiety in the presence of a Lewis acid; (e) forming a first intermediate compound wherein the oxo group on the C-3 carbon is converted to a hydroxy group by virtue of nucleophilic addition when the compound containing the nucleophilic aromatic moiety is contacted to the C-3 carbon of the flavan-3-one, (f) subjecting the first intermediate compound to dehydration so as to introduce a double bond between the C-3 carbon and C-4 carbon of the intermediate compound with the concomitant removal of the hydroxy group from the C-3 carbon to form an optically active flavene compound which is substituted by the nucleophilic aromatic moiety on the C-3 carbon, (g) optionally subjecting the resultant flavene compound to hydroboration-oxidation hydration thereby removing said double bond between the C-3 carbon and the C-4 carbon with the concomitant introduction of a hydroxy group at the C-4 carbon to form a second intermediate compound, (h) further optionally oxidizing the second intermediate compound of step (g) thereby converting the hydroxy group at the said C-4 carbon to an oxo group, thereby forming a biflavonoid or biflavonoid analogue which is substituted by the selected nucleophilic aromatic moiety on the C-3 carbon, (i) further optionally, and alternatively to step (h), subjecting the resultant flavene compound of step (f) to OsO 4 dihydroxylation thereby removing said double bond between the C-3 carbon and C-4 carbon with the concomitant introduction of a hydroxy group at the C-4 carbon and a hydroxy group at the C-3 carbon to form a third intermediate compound, and (j) subjecting the third intermediate compound to dehydration whereby the hydroxy group at the C-3 carbon is removed and a double bond is introduced between the C-3 carbon and C-4 carbon thereby forming an enol product and allowing such enol product to rearrange spontaneously to form a biflavonoid or biflavonoid analogue having an oxo group at its C-4 carbon and which is substituted by the selected nucleophilic aromatic moiety on its C-3 carbon.

  该发明涉及一种从起始物质或中间体中选择的光学不活性和光学活性化合物的制备方法，所述化合物选自C-3偶联的双黄酮类化合物和C-3偶联的双黄酮类似物，所述起始物质或中间体分别选自光学不活性或光学活性的黄酮-3-醇和光学活性的黄酮-3-酮，所述方法包括以下步骤：(a)提供具有黄酮-3-醇结构或为黄酮-3-酮的化合物，该化合物是光学不活性或活性的；(b)如果选择具有C-3碳上羟基的黄酮-3-醇结构化合物作为起始物质，则将具有黄酮-3-醇结构的化合物的C-3碳上的羟基转化为羟基，形成该化合物的黄酮-3-酮；(c)提供具有亲核芳香基团的化合物，所述化合物选自具有亲核芳香基团的化合物和具有黄酮类基本结构的化合物以及具有亲核芳香基团的化合物和不具有黄酮类基本结构的化合物；(d)在存在Lewis酸的情况下，将步骤(a)提供或步骤(b)获得的黄酮-3-酮与含有亲核芳香基团的化合物接触；(e)形成第一中间化合物，其中通过亲核加成使含有亲核芳香基团的化合物与黄酮-3-酮的C-3碳接触时，C-3碳上的羟基转化为羟基；(f)将第一中间化合物脱水，以在中间化合物的C-3碳和C-4碳之间引入双键，并同时去除C-3碳上的羟基，形成由亲核芳香基团取代C-3碳上的光学活性黄烯化合物；(g)可选地将所得的黄烯化合物经过氢硼氧化水合反应，从而去除C-3碳和C-4碳之间的双键，并同时在C-4碳引入羟基，形成第二中间化合物；(h)可选地进一步氧化步骤(g)中的第二中间化合物，将C-4碳上的羟基转化为羟基，从而形成在C-3碳上由所选亲核芳香基团取代的双黄酮或双黄酮类似物；(i)可选地，作为步骤(h)的替代，将步骤(f)中的所得黄烯化合物经过OsO4二羟基化反应，从而去除C-3碳和C-4碳之间的双键，并同时在C-4碳和C-3碳引入羟基，形成第三中间化合物；(j)将第三中间化合物脱水，从而去除C-3碳上的羟基，并在C-3碳和C-4碳之间引入双键，从而形成烯醇产物，并使该烯醇产物自发重排，形成在其C-4碳上具有羟基的双黄酮或双黄酮类似物，并在其C-3碳上由所选亲核芳香基团取代。
• [EN] COMPOUNDS, COMPOSITION AND USES THEREOF FOR TREATING CANCER<br/>[FR] COMPOSÉS, COMPOSITION ET LEURS UTILISATIONS DANS LE TRAITEMENT DU CANCER
  申请人：ROUSSY INST GUSTAVE

  公开号：WO2018189210A1

  公开（公告）日：2018-10-18

  The present invention relates to the fields of medicine and cancer treatment. The invention more specifically relates to new compounds which are typically for use as a medicament. In particular, the invention relates to the use of these new compounds for increasing the presentation, typically the production and presentation, of Pioneer Translation Products (PTPs)-derived antigens by cancer cells in a subject, and inducing or stimulating an immune response in the subject. The present disclosure also relates to uses of such compounds, in particular to prepare a pharmaceutical composition and/or to allow or improve the efficiency of a cancer therapy in a subject in need thereof. The invention also discloses methods for preventing or treating cancer, cancer metastasis and/or cancer recurrence in a subject. The present invention in addition provides kits suitable for preparing a composition according to the present invention and/or for implementing the herein described methods.

  本发明涉及医学和癌症治疗领域。该发明更具体地涉及通常用作药物的新化合物。特别是，该发明涉及利用这些新化合物来增加在受试者的癌细胞中由先驱翻译产物（PTPs）衍生的抗原的表达，通常是生产和展示，并在受试者中诱导或刺激免疫反应。本公开还涉及这些化合物的用途，特别是制备药物组合物和/或允许或改善受试者中癌症治疗的效率。该发明还揭示了用于预防或治疗受试者的癌症、癌症转移和/或癌症复发的方法。此外，本发明还提供了适用于根据本发明制备组合物和/或实施本文所述方法的试剂盒。
• Phosphodiesterase inhibitors
  申请人：Bernard Philippe

  公开号：US20070161628A1

  公开（公告）日：2007-07-12

  The invention relates especially to novel stereospecific derivatives of 2,3-benzodiazepine type as inhibitors of phosphodiesterases, especially 2 and 4, and uses thereof in the therapeutic field, most particularly for preventing and treating pathologies involving a central and/or peripheral disorder. The compounds of the invention more particularly correspond to the general formulae (I) and (II):

  该发明特别涉及2,3-苯二氮䓬啶类的新立体特异性衍生物，作为磷酸二酯酶，特别是2和4的抑制剂，以及在治疗领域中的用途，尤其是用于预防和治疗涉及中枢和/或外周障碍的病理。该发明的化合物更特别地对应于一般式(I)和(II)：
• METHODS OF DESIGNING, PREPARING, AND USING NOVEL PROTONOPHORES
  申请人：Martineau Louis C.

  公开号：US20140135359A1

  公开（公告）日：2014-05-15

  The present invention provides a computer-assisted method of generating a protonophore requiring the use of a computer including a processor. The method includes: designing the protonophore, calculating, using the processor, an estimated protonophoric activity; producing the protonophore if the estimated protonophoric activity corresponds to an U 50 of about 20 μM or less; and determining the uncoupling activity of the protonophore. The present invention also provides novel protonophores that meet the above requirement and their methods of use.

  本发明提供了一种利用计算机辅助的方法来生成需要使用处理器的质子载体。该方法包括：设计质子载体，使用处理器计算估计的质子载体活性；如果估计的质子载体活性对应于大约20微米或更少的U50，则生产质子载体；并确定质子载体的解耦活性。本发明还提供了符合上述要求的新型质子载体及其使用方法。
• NEW USE FOR A COMPOUND AS A MATRIX IN THE SPECIFIC DETECTION, IDENTIFICATION AND/OR QUANTIFICATION OF ALKALOIDS BY MALDI-TOF MASS SPECTROMETRY
  申请人：Dias Marylène

  公开号：US20140319331A1

  公开（公告）日：2014-10-30

  There is provided (i) a method of analysing small molecules that may have a mass of <800 Da, in particular alkaloids, said method being generally referred to as MALDI-TOF-MS (or MALDI time-of-flight mass spectrometry), which is an acronym for a method of analysis by matrix-assisted laser desorption/ionisation time-of-flight mass spectrometry. Also provided is (ii) a molecule according to formula (I) and the use of the molecule as a matrix in the analysis method.

  提供了一种分析可能具有质量小于800 Da的小分子的方法，特别是生物碱，该方法通常被称为MALDI-TOF-MS（或MALDI飞行时间质谱），这是一种通过基质辅助激光解吸/电离飞行时间质谱分析的方法的首字母缩写。还提供了一种根据式（I）的分子以及将该分子用作分析方法中的基质的用途。