络塞维 | 84954-92-7

• 物质功能分类: 生物化工 - 天然产物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: 络塞维
• 中文别名: 洛塞维；络赛维
• 英文名称: cinnamyl 6-O-(α-L-arabinopyranosyl)-β-D-glucopyranoside
• 英文别名: rosarin；rosavin；3-[6-O-(α-L-arabinopyranosyl)-β-D-glucopyranosyl]-oxy-1-phenylpropene；(2R,3R,4S,5S,6R)-2-[(E)-3-phenylprop-2-enoxy]-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• CAS: 84954-92-7
• 化学式: C₂₀H₂₈O₁₀
• 分子量: 428.436
• InChiKey: RINHYCZCUGCZAJ-IPXOVKFZSA-N

物化性质

• 熔点：
  171～173℃
• 沸点：
  709.1±60.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)
• 溶解度：
  在水中的溶解度为≥5mg/mL（加热）

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  158
• 氢给体数：
  6
• 氢受体数：
  10

安全信息

• 安全说明：
  S24/25
• WGK Germany：
  3
• 海关编码：
  29329990
• 储存条件：
  -20°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Rosavin
: SML0336
CAS-No. : 84954-92-7

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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
This substance is not classified as dangerous according to Directive 67/548/EEC.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Rosavidin
2E)-3-Phenylprop-2-en-1-yl 6-O-?-L-arabinopyranosyl-b-D-
glucopyranoside
(2R,3R,4S,5S,6R)-2-[(E)-3-Phenylprop-2-enoxy]-6-([(2S,3R,4S,5S)-3,4,5-
trihydroxyoxan-2-yl]oxymethyl)oxane-3,4,5-triol
(E)-3-Phenyl-2-propenyl 6-O-a-L-arabinopyranosyl- b-D-glucopyranoside
Formula : C20H28O10
Molecular Weight : 428,43 g/mol

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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
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
Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Avoid
breathing dust.
Environmental precautions
Do not let product enter drains.
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
Avoid formation of dust and aerosols.
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
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).

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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 not applicable
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. 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: - 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

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

络塞维主要用于抗疲劳、抗缺氧、缓解压力、提高工作效率和治疗神经系统的功能型疾病。其主要来源为玫瑰红景天（RhodioLa rosea L.），尤其是其根茎。

生物活性

Rosavin 从 R. rosea 中提取。研究显示，Rosavin 在小鼠模型中显示出抗抑郁、适应原性和抗焦虑作用。

化学性质

络塞维是一种黄色膏体，可溶于甲醇、乙醇和 DMSO 等有机溶剂，来源于玫瑰红景天。

用途

络塞维具有抗疲劳、抗缺氧、抗微波辐射和抗毒的作用。此外，它还用于含量测定、鉴定及药理实验等。

药理药效

主要作用为增强免疫力、消除忧郁感以及保护心血管系统。

反应信息

• 作为反应物：
  描述：

  络塞维 在 吡啶 、 盐酸 作用下， 反应 24.5h， 生成 乙酸肉桂酯
  参考文献：
  名称：

  Glycosides of cinnamyl alcohol from the rhizomes ofRhodiola rosea

  摘要：

  DOI：

  10.1007/bf00579423
• 作为产物：
  描述：

  cinnamyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-α-L-arabinopyranosyl)-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以 二氯甲烷 为溶剂， 以98.6 %的产率得到络塞维
  参考文献：
  名称：

  一种络塞维的晶型及其制备方法

  摘要：

  本发明公开了一种络塞维的晶型及其制备方法。具体公开了一种络塞维的制备方法，其包括如下步骤：将络塞维粗品与溶剂混合，进行析晶，得到络塞维的晶体；所述的溶剂为甲醇与“乙酸乙酯和/或二氯甲烷”的混合溶液。本发明的晶型具有良好的稳定性，吸湿性较弱，易于储存，对药物的优化和开发具有重要的价值。

  公开号：

  CN115124580A

文献信息

• Synthesis of the Rhodiola rosea glycoside rosavin
  作者：S. A. Patov、V. V. Punegov、A. V. Kuchin

  DOI：10.1007/s10600-006-0165-8

  日期：2006.7

  A synthetic scheme was proposed for the glycoside rosavin that includes a one-step glycosylation of cinnamyl alcohol with a disaccharide. The structure of the product was confirmed by PMR and 13C NMR spectroscopy.

  提出了一种糖苷罗沙文的合成方案，包括肉桂醇与二糖的一步糖基化。通过 PMR 和 13C NMR 光谱证实了产品的结构。
• 一种络塞维的合成方法
  申请人：济南山目生物医药科技有限公司

  公开号：CN110627845A

  公开（公告）日：2019-12-31

  本发明提供了一种络塞维的合成方法：在保护气氛中，除水剂存在下，三氟甲磺酸三甲基硅酯催化2,3,4‑三‑O‑乙酰基‑L‑呋喃阿拉伯糖三氯乙酰亚胺酯和乙基2,3,4‑三‑O‑乙酰基‑beta‑D‑硫代吡喃葡萄糖苷在有机溶剂中反应，然后将beta‑(E)‑肉桂醇、NIS和TfOH依次加入继续反应至完全，加入反应猝灭剂，分离获得中间体粗品，然后将中间体粗品与甲醇钠在甲醇中反应，分离纯化获得络塞维。本发明以商品化的L‑阿拉伯糖供体、D‑葡萄糖受体和beta‑(E)‑肉桂醇为原料，经三步反应得到高纯度的络塞维产品，中间体不需要纯化，终产品经析晶获得，总收率70%以上。本发明的方法体系反应干净，产物可以直接从体系中析晶分离，产物收率高、纯度高，有利于洛塞维的大规模产业化制备。
• Medicinal herbal extract carpediol for treating depression
  申请人：SWEDISH HERBAL INSTITUTE

  公开号：US20030194449A1

  公开（公告）日：2003-10-16

  The present invention is directed to anti-depressive activity of Crassulaceae special extracts, Carpediol, containing 2-(4-hydroxyphenyl)ethyl-&bgr;-d-glucopyranoside or 3-[6-o-(&agr;-1-arabinopyranosyl)-&bgr;-d-glucopyranosyl)-&bgr;-d-glucopyranosyl]-oxy-1-phenylpropene in mammals, to method of preparation and analysis of these extract, as well to safety of their usage in combination with other drugs.

  本发明涉及含有2-(4-羟基苯基)乙基-&bgr;-d-吡喃葡萄糖苷或3-[6-o-(&agr;-1-阿拉伯吡喃糖基)-&bgr；和 3-[6-o-(&agr;-1-阿拉伯吡喃糖基)-&bgr;-d-吡喃葡萄糖基]-氧-1-苯基丙烯在哺乳动物中的作用，以及这些提取物的制备和分析方法，以及它们与其他药物联合使用的安全性。
• 一种络塞维中间体、其制备方法和用途
  申请人：上海医药工业研究院

  公开号：CN115124578A

  公开（公告）日：2022-09-30

  本发明公开了一种络塞维中间体、其制备方法和用途。其中，具体公开了一种如式P8所示的化合物的制备方法，其包括以下步骤：(1)溶剂中，如式P6所示的化合物与BzCl进行羟基保护反应，得如式P7所示的化合物；(2)溶剂中，在酸的作用下，如式P7所示的化合物进行脱保护反应，得如式P8所示的化合物。还公开了所述如式P6所示的化合物用于制备络塞维的用途。本发明方法成本低、反应时间短、收率高、环保，且避免了柱层析步骤易于操作，适合放大生产。
• 一种络塞维中间体的制备方法
  申请人：上海医药工业研究院

  公开号：CN115124579A

  公开（公告）日：2022-09-30

  本发明公开了一种络塞维中间体的制备方法。具体公开了一种如式P6所示的化合物的制备方法，其包括如下步骤：溶剂中，在缚酸剂的作用下，如式P5所示的化合物与叔丁基二甲基氯硅烷(TBDMSCl)进行羟基保护反应，得如式P6所示的化合物；所述缚酸剂为咪唑。本发明方法成本便宜、收率及纯度高、且避免了柱层析步骤易于操作，适合放大生产。