天竺葵素-3-氯化葡萄糖苷 | 18466-51-8

• 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 - 黄酮类化合物
• 中文名称: 天竺葵素-3-氯化葡萄糖苷
• 中文别名: 天竺葵素-3-葡萄糖苷；天竺葵素葡萄糖苷；氯化翠菊苷
• 英文名称: pelargonidin-3-glucoside chloride
• 英文别名: 3-(β-D-glucopyranosyloxy)-5,-7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride；3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxyphenyl)-1-benzopyrylium chloride；pelargonidin 3-O-β-glucopyranoside chloride；pelargonidin‐3‐O‐glucoside；pelargonidin 3-β-D-glucoside chloride；pelargonidin 3-O-β-glucoside；Pelargonidin 3-glucoside；(2S,3R,4S,5S,6R)-2-[5,7-dihydroxy-2-(4-hydroxyphenyl)chromenylium-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol;chloride
• CAS: 18466-51-8
• 化学式: C₂₁H₂₁O₁₀*Cl
• mdl: MFCD00017578
• 分子量: 468.845
• InChiKey: CAHGSEFWVUVGGL-UBNZBFALSA-N

物化性质

• 溶解度：
  氯仿：可溶，二氯甲烷：可溶，DMSO：可溶，乙酸乙酯：可溶

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  161
• 氢给体数：
  7
• 氢受体数：
  10

安全信息

• WGK Germany：
  3
• 储存条件：
  -20°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : Callistephin chloride
CAS-No. : 18466-51-8
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
Caution - substance not yet tested completely.
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : Pelargonidin 3-O-glucoside chloride
3-(Glucosyloxy)-4′,5,7-trihydroxyflavylium chloride
Formula : C21H21ClO10
Molecular Weight : 468,84 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
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, Hydrogen chloride gas
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
Store under inert gas. Moisture sensitive.
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
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
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.
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: powder
Colour: brown
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.
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
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

概述

天竺葵素-3-O-葡萄糖苷（Pelargonidin 3-O-glucoside，以下简称Pg3G）是花色苷中最具有代表性的化合物之一，其水溶性较好。目前在草莓、红树莓、红皮萝卜、山竹皮和黑豆等多种果蔬中均发现了Pg3G的存在。其中，草莓中的花色苷主要以Pg3G为主，含量占80-95%，使其成为较为理想的Pg3G提取原料。研究表明，Pg3G具有抗氧化及防护氧化应激损伤的功效，因此不仅可以作为天然色素用于食品加工，还能作为天然抗氧化剂及功能食品因子应用于保健食品的开发。

天竺葵素-3-氯化葡萄糖苷是天竺葵素-3-O-葡萄糖苷的氯化物。

制备

将9.75mg（0.020mmol）山奈酚-3-（6-O-乙酰基）葡糖苷与164mg锌粉在真空条件下干燥后放入反应器中。随后，向反应器内通入氩气并制成氩气气氛。将温度降至0℃，在超声波照射下加入3.5%氯化氢-无水甲醇溶液（1.2ml），进行7分钟的超声波照射和强力搅拌后，在干燥条件下过滤反应混合物，并去除锌粉，得到滤液。

将上述滤液与干燥空气接触并强烈搅拌，反应持续3.5小时。此过程中，反应混合物的颜色从浅红色变为深红色。然后将混合物倒入水中（30ml），并通过填充有“Amberlite XAD-7凝胶”柱（内径1.5cm、高17cm）进行染料分子的吸附，该柱用0.5％TFA水溶液替代。接着使用0.5％TFA水溶液（250ml）洗涤柱子，然后加入含0.5％TFA的90%乙腈水溶液以洗脱柱中吸附的染料。

通过制备分离ODS-HPLC精制颜料级分。HPLC分析结果显示颜料部分含有两种花青素成分。随后在40℃、减压条件下将得到的颜料部分浓缩至干，最终获得了5.8mg天竺葵苷-3-（6-O-乙酰基）葡糖苷（产率50%）和5.4mg天竺葵素-3葡萄糖苷（产率50%）。通过与盐酸反应制备天竺葵素-3-氯化葡萄糖苷。所有颜料的纯度均不低于95%。

反应信息

• 作为反应物：
  描述：

  天竺葵素-3-氯化葡萄糖苷 在 水 作用下， 生成 2-(4-Hydroxy-phenyl)-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-2H-chromene-2,5,7-triol
  参考文献：
  名称：

  3-甲氧基-和3-（β-D-Glucopyranosyloxy）黄酮离子的合成。黄酮取代模式对水溶液中花色苷反应性的影响

  摘要：

  描述了3-糖基氧基化的黄酮离子（花青素），特别是天然花青素Callistephin（4）的合成。研究了合成颜料3和4在水溶液中的结构转变以及与绿原酸（7）和咖啡因（8）的分子络合，并将其与相应的3-甲氧基黄酮离子1和2以及卵磷脂（5）进行了比较。）和马尔文（6），两种非常常见的天然花青素。就糖基氧基残基在花色苷的化学性质中所起的作用进行了讨论。花色苷分子的络合（色素沉着）通过UV / VIS光谱和1 H-NMR进行定量研究。特别是，使用一般的理论处理方法来解释UV / VIS光谱数据，例如，可以证明无色形式的花色苷与8之间形成了分子配合物。

  DOI：

  10.1002/hlca.19940770616
• 作为产物：
  描述：

  4-(2-hydroxyacetyl)phenyl acetate 在 盐酸 、 calcium sulfate 、 氢氧化钾 、 4 A molecular sieve 、 氰化汞 作用下， 以 甲醇 、 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 53.0h， 生成 天竺葵素-3-氯化葡萄糖苷
  参考文献：
  名称：

  3-甲氧基-和3-（β-D-Glucopyranosyloxy）黄酮离子的合成。黄酮取代模式对水溶液中花色苷反应性的影响

  摘要：

  描述了3-糖基氧基化的黄酮离子（花青素），特别是天然花青素Callistephin（4）的合成。研究了合成颜料3和4在水溶液中的结构转变以及与绿原酸（7）和咖啡因（8）的分子络合，并将其与相应的3-甲氧基黄酮离子1和2以及卵磷脂（5）进行了比较。）和马尔文（6），两种非常常见的天然花青素。就糖基氧基残基在花色苷的化学性质中所起的作用进行了讨论。花色苷分子的络合（色素沉着）通过UV / VIS光谱和1 H-NMR进行定量研究。特别是，使用一般的理论处理方法来解释UV / VIS光谱数据，例如，可以证明无色形式的花色苷与8之间形成了分子配合物。

  DOI：

  10.1002/hlca.19940770616

文献信息

• Production of flavonoids by recombinant microorganisms
  申请人：Koffas Mattheos

  公开号：US20060019334A1

  公开（公告）日：2006-01-26

  Methods and compositions are provided for production of flavonoids in microbial hosts. The compositions comprises a set of genes which encode for enzymes involved in one or more steps in the biosymthetic pathway for the conversion of phenylpropanoids to various flavonoids. The method comprises the steps of introducing the set of genes into a heterologous host cell, allowing growth of the cells in a suitable medium such that the expression of the genes results in production of enzymes. When specific substrate(s) is/are provided to the transformed cell, the enzymes act on the substrate(s) to produce the desired flavonoids.

  本发明提供了一种在微生物宿主中生产黄酮类化合物的方法和组合物。该组合物包括一组基因，这些基因编码参与苯丙烷类物质转化为各种黄酮类化合物生物合成途径中的酶。该方法包括将该基因组引入异源宿主细胞中，让细胞在适宜培养基中生长，使得基因的表达导致酶的产生。当将特定底物提供给转化后的细胞时，酶作用于底物以产生所需的黄酮类化合物。
• MANUFACTURING METHOD FOR POLYPHENOL COMPOSITION
  申请人：Yamada Yasushi

  公开号：US20130085270A1

  公开（公告）日：2013-04-04

  A method for producing a polyphenol composition including a step of subjecting (A) a hardly water-soluble polyphenol and (B) one or more selected from cathechins, chlorogenic acids and methylated compounds of hardly water-soluble polyphenols to a heat treatment at from 100 to 180° C. in the presence of an aqueous medium.

  一种生产多酚组合物的方法，包括以下步骤：在水介质中，在100至180°C的温度下，将（A）一种难溶于水的多酚和（B）从儿茶素、绿原酸和难溶于水的多酚的甲基化化合物中选择一种或多种进行热处理。
• Selective Iodination Enables Anthocyanin Synthesis to Be More General
  作者：Jun Hu、Yue Li、Guangkai Wu、Shuer Liang、Zihan Zhao、Jia Liu、Jiali Chen、Guocan Yu、Jianxia Sun、Weibin Bai

  DOI：10.1021/acs.orglett.3c00597

  日期：——

  The current synthesis routes of anthocyanins are relatively complicated, which significantly hinders their development. We optimized the method by introducing a selective iodination reaction and also established a general scheme for preparing anthocyanin diglycosides. This method allows anthocyanin synthesis to require fewer steps and costs. Based on this, we prepared four common anthocyanins and two

  目前花青素的合成路线较为复杂，严重制约了其发展。我们通过引入选择性碘化反应优化了该方法，并建立了制备花青素二糖苷的通用方案。这种方法允许花青素合成需要更少的步骤和成本。基于此，我们制备了四种常见的花青素和两种花青素二葡萄糖苷，并测量了它们的抗氧化和抗胰岛素抵抗活性。
• LIQUID SEASONING
  申请人：Kao Corporation

  公开号：EP1949798A1

  公开（公告）日：2008-07-30

  The present invention is a liquid seasoning containing the following (A), (B), and (C): (A) 0.4 to 8% by mass of sodium (B) 0.01 to 4% by mass of flavonoid (C) 1 to 10% by mass of ethanol wherein, the flavonoid (B) satisfies the formula (1) and/or has one or more OH groups on the A-ring or B-ring in a molecule and no OH group at the position adjacent to the OH group (ortho position). Y/X+Y=0.05to1 wherein, X and Y represent the following numbers, respectively: X; the number of OH group bonded to benzene rings in a molecule of the flavonoid, Y; the number of OCH3 group bonded to benzene rings in a molecule of the flavonoid.

  本发明是一种液体调味料，含有以下(A)、(B)和(C)： (A) 0.4%至 8%（按质量计）钠 (B) 0.01 至 4%（按质量计）的黄酮类化合物 (C) 1%至 10%（以质量计）乙醇 其中，类黄酮（B）满足式（1）和/或在分子中的 A 环或 B 环上有一个或多个 OH 基团，而在与 OH 基团相邻的位置（正交位置）没有 OH 基团。Y/X+Y=0.05to1 其中，X 和 Y 分别代表以下数字： X：类黄酮分子中与苯环结合的 OH 基团的数目、 Y；类黄酮分子中与苯环结合的 OCH3 基团的数目。
• FLAVONOID GLYCOSYLTRANSFERASE AND UTILIZATION THEREOF
  申请人：International Flower Developments Proprietary Limited

  公开号：EP1985704A1

  公开（公告）日：2008-10-29

  A novel flavonoid glucosyltransferase originating from rose, a nucleic acid encoding that enzyme, for example, a flavonoid glucosyltransferase having an amino acid sequence indicated in SEQ ID NO. 2 or SEQ ID NO. 4, a nucleic acid encoding that enzyme, a method for changing the color of a rose flower using that nucleic acid, and a rose plant capable of changing color, are provided.

  本发明提供了一种源自玫瑰的新型类黄酮葡萄糖基转移酶、一种编码该酶的核酸（例如，具有 SEQ ID NO.2 或 SEQ ID NO.4 所示氨基酸序列的类黄酮葡萄糖基转移酶）、一种编码该酶的核酸、一种使用该核酸改变玫瑰花颜色的方法以及一种能够改变颜色的玫瑰植物。