奥沙京 | 482-53-1

• 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 - 异黄酮类化合物
• 中文名称: 奥沙京
• 英文名称: osajin
• 英文别名: 9-hydroxy-7-(p-hydroxyphenyl)-2,2-dimethyl-10-(3-methyl-2-butenyl)-1,5-dioxa-2H-phenanthren-8-one；5-hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one
• CAS: 482-53-1
• 化学式: C₂₅H₂₄O₅
• mdl: MFCD00076045
• 分子量: 404.463
• InChiKey: DCTLJGWMHPGCOS-UHFFFAOYSA-N

物化性质

• 熔点：
  189° (uncorr), 193° (corr)
• 沸点：
  632.3±55.0 °C(Predicted)
• 密度：
  1.258±0.06 g/cm3(Predicted)
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。
• 碰撞截面：
  201.4 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  76
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 危险品标志：
  N
• 安全说明：
  S61
• 危险类别码：
  R50
• WGK Germany：
  3
• 储存条件：
  -20°C

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
Product name : Osajin
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. : 482-53-1
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
Classification according to Regulation (EC) No 1272/2008
Acute aquatic toxicity (Category 1), H400
Chronic aquatic toxicity (Category 1), H410
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
N Dangerous for the R50
environment
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)
H410 Very toxic to aquatic life with long lasting effects.
Precautionary statement(s)
P273 Avoid release to the environment.
P501 Dispose of contents/ container to an approved waste disposal plant.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Molecular Weight : 404,46 g/mol
CAS-No. : 482-53-1
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Osajin
Aquatic Acute 1; Aquatic -
Chronic 1; H410
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Osajin
N, R50 -
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
no data available
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 vapours, mist or gas. Ensure adequate ventilation.
For personal protection see section 8.
Environmental precautions
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the
environment must be avoided.
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
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.
Recommended storage temperature: -20 °C
Specific end use(s)
A part 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
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
Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into
the environment must be avoided.

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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 194 °C
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- log Pow: 5,599
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

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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
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
Very toxic to aquatic life with long lasting 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: 3077 IMDG: 3077 IATA: 3077
UN proper shipping name
ADR/RID: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (Osajin)
IMDG: ENVIRONMENTALLY HAZARDOUS SUBSTANCE, SOLID, N.O.S. (Osajin)
IATA: Environmentally hazardous substance, solid, n.o.s. (Osajin)
Transport hazard class(es)
ADR/RID: 9 IMDG: 9 IATA: 9
Packaging group
ADR/RID: III IMDG: III IATA: III
Environmental hazards
ADR/RID: yes IMDG Marine pollutant: yes IATA: yes
Special precautions for user
Further information
EHS-Mark required (ADR 2.2.9.1.10, IMDG code 2.10.3) for single packagings and combination
packagings containing inner packagings with Dangerous Goods > 5L for liquids or > 5kg for solids.

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

生物活性

Osajin 是存在于 Maclura pomifera 果实中的一种主要生物活性异黄酮，具有抗肿瘤、抗氧化和抗炎作用。

靶点

• 凋亡：Osajin 显著抑制人鼻咽癌细胞（TW076, CG1 和 TW04 细胞）的存活率，呈剂量依赖性。Osajin 通过多种凋亡途径诱导人鼻咽癌细胞凋亡，包括外在死亡受体途径和内在通路，该途径依赖于线粒体和内质网应激。此外，Osajin 在六种人类癌细胞系（肾、肺、前列腺、乳腺、黑色素瘤和结肠癌细胞）中表现出生长抑制活性。

体外研究

• Osajin 显著降低人鼻咽癌细胞 (TW076, CG1 和 TW04 细胞) 的存活率，呈剂量依赖性。Osajin 通过多种凋亡途径诱导人鼻咽癌细胞凋亡，包括外在死亡受体途径和内在通路（依赖于线粒体和内质网应激）。此外，Osajin 在肾、肺、前列腺、乳腺、黑色素瘤和结肠癌等六种人类癌细胞系中表现出生长抑制活性。

体内研究

• Osajin 和 pomiferin 减轻了缺血再灌注引起的肌心功能障碍。这通过增加抗氧化酶的水平和总抗氧化活性得到证实。Osajin 和 pomiferin 的治疗提供的心脏保护作用来源于对氧化应激的抑制，这也与心室功能的改善相关。

反应信息

• 作为反应物：
  描述：

  奥沙京 在 四丁基溴化铵 、 硝酸 作用下， 以 水 、 1,2-二氯乙烷 为溶剂， 反应 72.0h， 以86%的产率得到
  参考文献：
  名称：

  来自Maclura pomifera的天然异黄酮的半合成衍生物，是一类新型的PDE-5A抑制剂。

  摘要：

  最近有报道称天然（异）黄酮类化合物可抑制环状核苷酸磷酸二酯酶（PDEs）并诱导血管舒张，尽管文献中描述的结果是不一致的。cGMP选择性同工型PDE-5A特别代表西地那非及其类似物，通过激活NO / cGMP途径促进血管平滑肌的松弛，从而治疗勃起功能障碍（ED）和肺动脉高压。我们进行了这项研究，以验证osajin和pomiferin，两种天然的异戊烯化异黄酮和Maclura pomifera提取物的主要成分是否先前对它们的抗癌，抗菌和抗糖尿病特性进行了研究，它们对PDE-5A均具有抑制作用。从植物提取物中分离出这两种异黄酮，然后进行合成修饰以获得一组在天然支架上进行了轻微和集中修饰的半合成衍生物。首先在体外针对PDE-5A筛选化合物，并基于令人鼓舞的结果，进一步测试了其对离体大鼠动脉环的松弛作用。还进行了计算对接研究，以探索与靶蛋白相互作用的方式。将获得的数据与众所周知的PDE-5A抑制剂西

  DOI：

  10.1016/j.fitote.2015.06.020
• 作为产物：
  描述：

  (E)-3-(dimethylamino)-1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)prop-2-en-1-one 在 吡啶 、 盐酸 、 copper(l) iodide 、 四(三苯基膦)钯 、 tris(6,6,7,7,8,8-heptafluoro-2,2-dimethyl-3,5-octadionato)europium(III) 、 乙醇 、 水 、 碘 、 三氯化硼 、 potassium carbonate 、 potassium iodide 、 potassium hydroxide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 、 三环己基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 二氯甲烷 、 水 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 54.0h， 生成 奥沙京
  参考文献：
  名称：

  天然异黄酮：Scandenone、Osajin 和 6,8-Diprenylgenistein 的全合成和抗菌研究

  摘要：

  异黄酮是一类天然产物，具有多种有趣的生物特性，包括抗氧化、保肝、抗菌和抗炎活性。 Scandenone (1)、osajin (2) 和 6,8-diprenylgenistein (3) 是天然异戊二烯异黄酮，具有相同的多酚骨架。本研究以关键中间体15为原料合成天然异黄酮1-3，建立了直链和角吡喃异黄酮的立体选择性合成方法。还对1-3的抗菌活性进行了评价，它们均对革兰氏阳性菌表现出良好的抗菌活性。其中，2是对MRSA最有效的一种，其MIC值为2 μg/mL，SEM分析表明2可以破坏MRSA和粪肠球菌的细菌细胞膜。这些结果表明，异黄酮类型可以作为开发治疗革兰氏阳性细菌感染的新型抗菌剂的先导。

  DOI：

  10.3390/molecules29112574

文献信息

• Synthesis and Biological Activity of Triazole Derivatives of Osajin
  作者：L.V. Ramana、K.M.Ch. Appa Rao、M. Suri Appa Rao、Ch. Venkata ramanaiah、G. Nageswara Rao

  DOI：10.14233/ajchem.2021.23195

  日期：——

  In the present study, osajin-1,2,3-triazole hybrids were designed, synthesized and evaluated for their anti-proliferative activity against MCF-7, PC-3 and Hela cell lines. Many of the synthesized hybrid derivatives were found potent than the parent compound, osajin (1). All the semi-synthesized derivatives (3a-j) were characterized by using mass and NMR spectroscopic techniques. Among the newly synthesized compounds, 3c, 3d, and 3e were shown promising activities against the tested cell lines compared with doxorubicin standard. In addition, molecular docking studies of the synthesized compounds have shown a good correlation with in silico molecular docking analysis by exhibiting strong interactions with the inhibitor HERA-protein.

  在本研究中，设计、合成并评估了osajin-1,2,3-三唑杂合物对MCF-7、PC-3和Hela细胞系的抗增殖活性。许多合成的杂合衍生物比母体化合物osajin（1）更具潜力。所有半合成衍生物（3a-j）均通过质谱和核磁共振光谱技术进行表征。在新合成的化合物中，3c、3d和3e显示出与阿霉素标准相比在测试细胞系中具有良好活性。此外，合成化合物的分子对接研究显示与体外分子对接分析具有良好的相关性，表现出与抑制剂HERA蛋白的强烈相互作用。
• Heteroleptic copper(II) complexes of prenylated flavonoid osajin behave as selective and effective antiproliferative and anti-inflammatory agents
  作者：Ján Vančo、Zdeněk Trávníček、Jan Hošek、Zdeněk Dvořák

  DOI：10.1016/j.jinorgbio.2021.111639

  日期：2022.1

  Heteroleptic copper(II) complexes, containing prenylated flavonoid osajin isolated from the fruits of Maclura pomifera Schneid., were prepared and thoroughly characterized, including single crystal X-ray analysis. Some of the following complexes of the general composition [Cu(L)(bpy)]NO3 (1), [Cu(L)(dimebpy)]NO3·2MeOH (2) [Cu(L)(phen)]NO3·H2O (3), [Cu(L)(bphen)]NO3 (4) and [Cu(L)(dppz)]NO3 (5), where

  制备了异配铜 (II) 配合物，其中含有从Maclura pomifera Schneid.果实中分离出的异戊二烯化黄酮 osajin ，并对其进行了彻底的表征，包括单晶 X 射线分析。以下一些一般组成的配合物 [Cu(L)(bpy)]NO 3 ( 1 ), [Cu(L)(dimebpy)]NO 3 ·2MeOH ( 2 ) [Cu(L)(phen)]NO 3 ·H 2 O ( 3 )、[Cu(L)(bphen)]NO 3 ( 4 ) 和 [Cu(L)(dppz)]NO 3 ( 5 )，其中 HL 代表 3-(4-羟基苯基) -5-羟基-8,8-二甲基-6-(3-甲基丁-2-烯-1-基)-4 H ,8 H-苯并[1,2- b :3,4- b' ]dipyran-4-one (osajin), bpy = 2,2'-bipyridine, dimebpy = 4,4'-dimethyl-2,2'-bipyridine
• [EN] HETEROLEPTIC COMPLEXES OF COPPER WITH OSAJIN OR POMIFERIN AND THEIR UTILIZATION FOR THE PREPARATION OF DRUGS FOR THE TREATMENT OF TUMOUR DISEASES<br/>[FR] COMPLEXES HÉTÉROLEPTIQUES DE CUIVRE AVEC DE L'OSAJINE OU DE LA POMIFÉRINE ET LEUR UTILISATION POUR LA PRÉPARATION DE MÉDICAMENTS POUR LE TRAITEMENT DE MALADIES TUMORALES
  申请人：UNIV PALACKEHO

  公开号：WO2021018324A1

  公开（公告）日：2021-02-04

  The invention provides the novel copper complexes in the oxidation state +II involving structural motif (I) and having the general formula [Cu(L)(LN)]X, where the symbol L represents a deprotonated derivative of 3-(4-hydroxyphenyl)-5-hydroxy-8,8-dimethyl-6-(3-methylbut-2-en-1-yl)-4H,8H-5benzo[1,2-b:3,4-b']dipyrane-4-one, osajin or pomiferin having the structural formula (II), and LN is bidentately coordinated N-donor ligand derived from 1,10-phenanthroline of the general formula (III) or 2,2'-bipyridine of the general formula (IV), and X represents a monoanion of acid selected from the group of: Cl-, NO3 -, HSO4 -, BF4 -, BPh4 -, HCOO-, CH3COO-. The complexes are designated for the preparation of drugs for the treatment of tumour diseases, particularly for the treatment of human ovarian carcinoma and/or human ovarian carcinoma resistant to cisplatin and/or human breast adenocarcinoma, human prostate carcinoma and/or human colorectal adenocarcinoma and/or human osteosarcoma and/or human lung adenocarcinoma.

  该发明提供了氧化态为+II的新型铜配合物，涉及结构基元（I），具有通式[Cu(L)(LN)]X，其中符号L代表3-(4-羟基苯基)-5-羟基-8,8-二甲基-6-(3-甲基丁-2-烯-1-基)-4H,8H-5苯并[1,2-b:3,4-b']二吡喃-4-酮、osajin或pomiferin的去质子衍生物，具有结构式（II），LN是从通式（III）的1,10-邻菲啰啉或通式（IV）的2,2'-联吡啉衍生的双齿配体，X代表来自以下酸单负离子组的酸的单负离子：Cl-、NO3-、HSO4-、BF4-、BPh4-、HCOO-、CH3COO-。这些配合物用于制备用于治疗肿瘤疾病的药物，特别是用于治疗人类卵巢癌和/或对顺铂耐药的人类卵巢癌和/或人类乳腺腺癌、人类前列腺癌和/或人类结肠腺癌和/或人类骨肉瘤和/或人类肺腺癌的治疗。
• New prenylated isoflavones and a prenylated dihydroflavonol from Millettia pachycarpa
  作者：Ashok K. Singhal、Ram P. Sharma、Gopalakrishna Thyagarajan、Werner Herz、Serengolam V. Govindan

  DOI：10.1016/0031-9422(80)85140-5

  日期：——

  Abstract Extraction of Millettia pachycarpa Benth. gave 5,7,4′-trihydroxy-6,8-diprenylisoflavone (1a), 5,7,4′-trihydroxy-6,3′-diprenylisoflavone (2a), 5,7,3′,4′-tetrahydroxy-6,8-diprenylisoflavone (3a) and (2R, 3R)-5,4′-dihydroxy-8-prenyl-6″,6″-dimethylpyrano[2″,3″: 7,6]-dihydroflavonol (4a) whose structures were established by chemical transformations and spectroscopic means. Pectolinarigenin and

  Millettia pachycarpa Benth的摘要提取。得到 5,7,4'-trihydroxy-6,8-diprenylisoflavone (1a), 5,7,4'-trihydroxy-6,3'-diprenylisoflavone (2a), 5,7,3',4'-tetrahydroxy- 6,8-diprenylisoflavone (3a) and (2R, 3R)-5,4'-dihydroxy-8-prenyl-6″,6″-dimethylpyrano[2″,3″: 7,6]-dihydroflavonol (4a)结构是通过化学转化和光谱方法建立的。Pectolinarigenin 和 Salvigenin 是从 Buddleia macrostachya Benth 中分离出来的。
• [EN] COMPOUNDS AND COMPOSITIONS THAT CAUSE MYCN AND/OR CMYC DEGRADATION AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS ET COMPOSITIONS QUI PROVOQUENT LA DÉGRADATION DE MYCN ET/OU DE CMYC ET LEURS PROCÉDÉS D'UTILISATION
  申请人：UNIV COLUMBIA

  公开号：WO2020123699A1

  公开（公告）日：2020-06-18

  The present disclosure provides, inter alia, scaffolds and compounds having the structure (I). Also provided are compositions containing a pharmaceutically acceptable carrier and one or more compounds according to the present disclosure. Further provided are methods for treating or ameliorating the effects of a cancer in a subject, methods for selectively killing a cancer cell, methods of modulating mTORC1/2 signaling activity in a cell, methods of modulating the activity of a Master Regulator for MycN in a subject having MycN-amplified neuroblastoma (MycNAMP NBL), methods of selectively treating or ameliorating effects of a cancer in a subject in need thereof, and platforms and methods for identifying a compound that induces degradation of a cancer-related protein. Also provided are kits comprising a compound or a pharmaceutical composition according to the present disclosure. Methods for treating cancers and methods for modulating MYC Master Regulators using other compounds are also provided.

  本公开提供了具有结构（I）的支架和化合物，以及含有药学上可接受的载体和一种或多种根据本公开的化合物的组合物。此外，还提供了治疗或改善受试者癌症影响的方法，选择性杀死癌细胞的方法，调节细胞中mTORC1 / 2信号活性的方法，调节MycN主调节因子在具有MycN放大的神经母细胞瘤（MycNAMP NBL）受试者中的活性的方法，选择性治疗或改善受试者癌症影响的方法，以及鉴定诱导癌相关蛋白降解的化合物的平台和方法。还提供了包含根据本公开的化合物或药物组合物的试剂盒。还提供了使用其他化合物治疗癌症和调节MYC主调节因子的方法。