丹酚酸 A | 96574-01-5

• 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 - 二苯乙烯类
• 中文名称: 丹酚酸 A
• 中文别名: (2R)-3-(3,4-二羟基苯基)-2-[(E)-3-[2-[(E)-2-(3,4-二羟基苯基)乙烯基]-3,4-二羟基苯基]丙-2-烯酰]氧丙酸；丹参酚酸A；丹酚酸A
• 英文名称: salvianolic acid A
• 英文别名: salvianolic acid；SAA；SalA；dan phenolic acid A；(2R)-3-(3,4-dihydroxyphenyl)-2-[(E)-3-[2-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]-3,4-dihydroxyphenyl]prop-2-enoyl]oxypropanoic acid
• CAS: 96574-01-5
• 化学式: C₂₆H₂₂O₁₀
• 分子量: 494.455
• InChiKey: YMGFTDKNIWPMGF-UCPJVGPRSA-N

物化性质

• 熔点：
  164-167°C
• 沸点：
  858.7±65.0 °C(Predicted)
• 密度：
  1.580±0.06 g/cm3(Predicted)
• 溶解度：
  在水中的溶解度为≥19mg/mL

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  185
• 氢给体数：
  7
• 氢受体数：
  10

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 吸湿性，存放于-20°C冷冻环境中，并在惰性气体氛围下保存 |

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Salvianolic acid A hydrate
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
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

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Dan phenolic acid A hydrate
Formula : C26H22O10 · xH2O
Molecular Weight : 494,45 g/mol

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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
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
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
Carbon oxides
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 vapors, mist or gas.
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.

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Section 7. HANDLING AND STORAGE
Precautions for safe handling
Provide appropriate exhaust ventilation at places where dust is formed.
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 uses
no data available

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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).

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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) Autoignition 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
no data available
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

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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 sensitization
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
Potential health effects
Inhalation
May be harmful if inhaled. May cause respiratory tract irritation.
Ingestion May be harmful if swallowed.
Skin May be harmful if absorbed through skin. May cause skin irritation.
Eyes May cause eye irritation.
Signs and Symptoms of Exposure
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.
Additional Information
RTECS: Not available

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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
no data available
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.

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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
no data available

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Section 16. OTHER INFORMATION
Further information
Copyright 2012 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

生物活性

Salvianolic acid A 可通过抑制基质金属钛酶 9 (MMP-9) 和发挥抗炎作用来保护血脑屏障。

靶点

| MMP-9 |

体内研究

Salvianolic acid A (SAA) 在治疗组中显示出显著的有益效果。20 mg/kg 的 Salvianolic acid A 可显著延长小鼠在平板上的停留时间。与假手术组相比，模型组的小脑水分含量显著增加，这一现象通过 Salvianolic acid A (10 和 20 mg/kg) 处理得到了显著缓解。与模型组相比，Salvianolic acid A (5, 10, 和 20 mg/kg) 可以维持正常的神经元结构并增加神经元数量。还发现，20 mg/kg 的 Salvianolic acid A 能够显著减少缺血-再灌注诱导的 MMP-9 过表达，而 MMP-2 表达未受显著影响。组织抑制剂金属蛋白酶 (TIMPs) 可通过高亲和力结合到金属蛋白酶催化域来抑制其活性。

化学性质

黄色针状结晶，可溶于甲醇、乙醇、DMSO 等有机溶剂，来源于丹参根茎。

用途

Salvianolic acid A 适用于治疗心绞痛及急性心肌梗塞后遗症和脑血栓形成。

此外，还可用于含量测定、鉴定以及药理实验。其药理作用包括抗凝血作用和显著的抗血小板聚集作用，以及抗分泌和抗溃疡作用等。

反应信息

• 作为反应物：
  描述：

  丹酚酸 A 在 sodium hydroxide 作用下， 以 水 为溶剂， 以948 g的产率得到salvianolic acid A sodium salt
  参考文献：
  名称：

  CN106748733

  摘要：

  公开号：
• 作为产物：
  描述：

  sodium danshensu 在 吗啉 、 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 potassium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 56.0h， 生成 丹酚酸 A
  参考文献：
  名称：

  由丹参素钠合成（+）-丹酚酸A

  摘要：

  （+）-丹酚酸A是传统中药丹参中活性最高的成分之一，已通过10步合成，总收率为6.5％。从廉价的原香草醛和丹参素钠（在我们的小组中通过不对称催化合成）开始，该过程包括以下内容：Wittig反应可得到具有绝对E-构型的所需产物，AlCl 3脱甲基反应的产率令人满意，以及对烯丙基基团进行实际的脱保护以提供最终产物（+）-丹酚酸A。当前的合成技术具有使用廉价的起始原料，反应条件温和的优势，并且具有用于大规模合成的潜力。

  DOI：

  10.1016/j.tet.2018.08.044

文献信息

• MYOCARDIAL REGENERATION PROMOTING COMPOUNDS, PREPARATION METHOD THEREOF, PHARMACEUTICAL COMPOSITION, AND THEIR USE
  申请人：GENHEALTH PHARMA CO., LTD.

  公开号：US20200317602A1

  公开（公告）日：2020-10-08

  The present invention discloses a novel 3-aryl-2-propen-1-one series derivative and the synthesis processes thereof. Besides, the present invention also discloses the series derivative as a pharmaceutical composition and their use for promoting myocardial regeneration.

  本发明公开了一种新型的3-芳基-2-丙烯-1-酮系列衍生物及其合成方法。此外，本发明还公开了该系列衍生物作为一种药物组合物，以及它们用于促进心肌再生的用途。
• 含有丹酚酸盐的组合物及其应用
  申请人：上海华汇拓医药科技有限公司

  公开号：CN108101788A

  公开（公告）日：2018-06-01

  本发明提供了丹酚酸化合物的二甲双胍盐及其药物组合物，本发明还涉及了此物质在预防和治疗糖尿病并发症方面的作用。
• The asymmetric total synthesis of (+)-salvianolic acid A
  作者：Yong Zheng、Wei-Bin Song、Li-Jiang Xuan

  DOI：10.1016/j.tet.2016.05.070

  日期：2016.8

  An asymmetric synthesis of (+)-salvianolic acid A with cardioprotective properties, has been accomplished in a convergent manner in eight steps and 10.6% overall yield. This synthesis features an asymmetric addition of organometallics to optically pure 2,3-epoxypropionate in the presence of BF3·Et2O, Ru(III)-catalyzed directed CH olefination, and I2-catalyzed isomerization reaction.

  具有收敛性的（+）-丹酚酸A的不对称合成以八步收敛的方式完成，总收率为10.6％。该合成的特征是在BF 3 ·Et 2 O，Ru（III）催化的定向C H烯烃化和I 2催化的异构化反应的存在下，将有机金属化合物不对称地添加到光学纯的2,3-环氧丙酸酯中。
• 一种丹酚酸A的制备方法
  申请人：山东省分析测试中心

  公开号：CN106431915B

  公开（公告）日：2019-04-23

  本发明公开了一种丹酚酸A的制备方法，步骤如下：(1)将丹酚酸B用pH为3.5‑4.5的NaOH或NaHCO3水配制成35‑45mg/mL的溶液，置于亚临界水反应釜中，加热炉达到170℃‑190℃并稳定后，将反应釜放入加热炉，50min‑70min后取出反应釜并放入冰水浴或冷水冲中冷却，将液体取出，冷冻干燥，得富含丹酚酸A粗品；(3)应用高速逆流色谱分离纯化丹酚酸A：溶剂系统为石油醚：乙酸乙酯：正丁醇：水＝2:3:1:9，上相加10mM三氟乙酸为固定相，下相为10mM氨水为流动相，高速逆流色谱仪柱体积为200‑400mL，上样量1.0‑1.2g，转速600‑1000rpm，流速1‑4mL/min，检测波长280nm。本发明方法成本低，操作简便，效率高，可以较大批量将丹酚酸粗提物进行转化，分离制备出纯度大于98％的丹酚酸A单体化合物。
• Chemical conversions of salvianolic acid B by decoction in aqueous solution
  作者：Hyoung Jae Lee、Jeong-Yong Cho、Jae-Hak Moon

  DOI：10.1016/j.fitote.2012.06.015

  日期：2012.10

  Salvianolic acid B (Sal B) is the most abundant phenolic compound in Salvia miltiorrhiza, which has been widely used for the treatment of cardiovascular diseases in Oriental medicine. To elucidate structure of the converted compounds of Sal B by decoction in aqueous solution, Sal B (200 mg) was decocted in an aqueous solution (200 mL) at pH 4.9 and the decocted solution was purified by Sephadex LH-20

  丹酚酸B（Sal B）是丹参中含量最丰富的酚类化合物，在东方医学中已被广泛用于治疗心血管疾病。为了通过在水溶液中煎煮来阐明Sal B转化化合物的结构，将Sal B（200 mg）在pH 4.9的水溶液（200 mL）中煎煮，并将煎煮的溶液通过Sephadex LH-20柱色谱法纯化并制备HPLC。分离出13种转化的化合物，并通过NMR和MS确定化学结构。除了先前报道的4种化合物通过水煎制而成的Sal B转化产物外，首次报道了9种化合物具有从水煎Sal B溶液中分离出的化合物的完整结构，并且其中三种化合物被确定为新化合物。此外，