甜叶悬钩子苷 | 64849-39-4

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: 甜叶悬钩子苷
• 中文别名: 甜茶苷
• 英文名称: rubusoside
• 英文别名: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,4S,5R,9S,10R,13S)-5,9-dimethyl-14-methylidene-13-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxytetracyclo[11.2.1.01,10.04,9]hexadecane-5-carboxylate
• CAS: 64849-39-4
• 化学式: C₃₂H₅₀O₁₃
• 分子量: 642.741
• InChiKey: YWPVROCHNBYFTP-OSHKXICASA-N

物化性质

• 熔点：
  178～181℃
• 沸点：
  802.5±65.0 °C(Predicted)
• 密度：
  1.45
• 溶解度：
  可溶于DMSO（轻微）、甲醇（轻微、超声处理）、水（轻微）
• 碰撞截面：
  241.31 Ų [M+H]+ [CCS Type: TW]

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  45
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  216
• 氢给体数：
  8
• 氢受体数：
  13

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 : Rubusoside
CAS-No. : 64849-39-4
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
Formula : C32H50O13
Molecular Weight : 642,73 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.
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

概述

甜茶苷与甜叶菊糖苷结构相似，仅在C13位缺少一个葡萄糖分子。甜茶苷是一种无毒、高甜度且低热值的天然甜味剂，具有多种健康益处，如降血压、降血糖和促进新陈代谢等作用。此外，它还能够缓解胃酸过多症状，并广泛应用于食品和医药工业领域，已成功出口至日本及东南亚等地。

制备

一种高效提取甜茶苷的方法包括以下步骤：

1. 采用5克过60目筛的甜茶粉末，加入15毫升0.3%十二烷基二甲基甜菜碱表面活性剂。
2. 冷浸15分钟后，以固液比1:15，在65℃下超声功率为200W的条件下提取35分钟。此步骤重复进行两次。
3. 抽滤并合并滤液后使用旋转蒸发仪浓缩至无醇味。
4. 采用60%乙醇过夜醇沉处理，然后以4000转/分钟离心20分钟后收集上清液。
5. 使用AB-8树脂进一步纯化，用3体积倍数（BV）的60%乙醇洗脱液洗脱。此洗脱液经过D941柱进一步进行脱色和去蛋白处理后合并。
6. 合并后的柱流液及5体积倍数（BV）水洗液通过聚酰胺柱除去多酚、黄酮和苦味物质。
7. 最终收集的纯净甜茶苷液用水淋洗至无甜味，再将此液体喷雾干燥以获得白色极甜的甜茶苷。

经测定，此方法从甜茶中提取出5.91%的甜茶苷，提取率达到98.5%，基本上没有苦涩味。

检测方法

CN201410705364.X报道了一种快速检测甜茶苷的方法。该方法包括以下步骤：

1. 分别配制甜茶苷的标准样品及待测试样溶液。
2. 将标准样品在紫外检测器的波长范围190～400纳米之间进行扫描，以确定最佳吸收波长。
3. 使用反相高效液相色谱法对样品进行分析。具体条件如下：
   • 色谱柱：C18（5μm，150×4.6mm i.d）；
   • 流动相组成的体积比：甲醇:水 = 50～80:10～30；
   • 流速：1.0 mL/min；
   • 柱温：30℃；
   • 进样量：3～5μL。
4. 建立标准曲线，从而求出待测试样品溶液中甜茶苷的含量。

生物活性

Rubusoside是一种天然甜味剂和增溶剂，具有良好的抗血管生成作用及抗过敏特性。

化学性质与用途

• 化学性质：白色结晶状固体，可溶于甲醇、乙醇、DMSO等有机溶剂。
• 用途：甜叶悬钩子苷具有降血糖、降血压和促进新陈代谢的作用。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  甜菊糖	stevioside	57817-89-7	C38H60O18	804.884
  甜菊醇19-葡萄糖苷	13-hydroxy-ent-kaur-16-en-19-oic acid β-D-glucopyranosyl ester	64977-89-5	C26H40O8	480.599
  13-(beta-D-吡喃葡萄糖基氧基)-(4alpha)-贝壳杉-16-烯-18-酸	steviolmonoside	60129-60-4	C26H40O8	480.599

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	rebaudioside G	127345-21-5	C38H60O18	804.884
  ——	13-O-β-Maltosyl-19-O-β-D-glucosyl-steviol	93973-87-6	C38H60O18	804.884
  ——	13-O-β-Maltotriosyl-19-O-β-D-glucosyl-steviol	93973-88-7	C44H70O23	967.026
  ——	13-O-β-D-Glucosyl-19-O-β-maltosyl-steviol	——	C38H60O18	804.884
  ——	13-O-β-D-Glucosyl-19-O-β-maltotriosyl-steviol	——	C44H70O23	967.026
  ——	13-O-β-D-glucosyl-19-O-β-maltotetrosylsteviol	134150-16-6	C50H80O28	1129.17
  ——	13-O-β-maltotetrosyl-19-β-D-glucosylsteviol	120602-95-1	C50H80O28	1129.17
  ——	13-O-β-maltosyl-19-O-β-maltotriosylsteviol	134150-15-5	C50H80O28	1129.17
  ——	13-O-β-maltotriosyl-19-O-β-maltosylsteviol	134150-14-4	C50H80O28	1129.17
  ——	13-O-β-D-glucosyl-19-O-β-maltopentosylsteviol	134150-21-3	C56H90O33	1291.31

反应信息

• 作为反应物：
  描述：

  甜叶悬钩子苷 在 UGT₇₆G₁ 、 UGT₉₁D₂ 、 magnesium chloride 作用下， 以 aq. phosphate buffer 为溶剂， 反应 1.0h， 生成 瑞鲍迪甙 A
  参考文献：
  名称：

  [EN] HIGH-PURITY STEVIOL GLYCOSIDES
  [FR] GLYCOSIDES DE STÉVIOL DE HAUTE PURETÉ

  摘要：

  描述了制备高度纯化的蒸馏甘甜苷，特别是蒸甘甜苷A、D和M的方法。这些方法包括利用重组微生物将各种原始成分转化为目标蒸甘甜苷。此外，还披露了新型蒸甘甜苷reb D2、reb M2和reb I，以及它们的制备方法。这些高度纯化的蒸甜苷可作为无热量甜味剂，用于食用和可咀嚼的产品，如任何饮料、糖果、烘焙产品、饼干和口香糖。

  公开号：

  WO2016043926A1
• 作为产物：
  描述：

  甜菊糖 在 immobilized β-galactosidase from Escherichia coli BL21 (DE3) pLysS 作用下， 生成 甜叶悬钩子苷
  参考文献：
  名称：

  Anti-cariogenic Characteristics of Rubusoside

  摘要：

  变形链球菌通过变形蔗糖酶活性从蔗糖合成粘性不溶性葡聚糖，从而在人类龋齿的发展中发挥重要作用。为了探讨蔷薇科悬钩子中天然甜味剂成分甜叶悬钩子苷 (Ru) 的抗龋齿特性，我们研究了 Ru 对变异蔗糖酶活性和变异链球菌生长的抑制作用。 Ru (50 mM) 对含有 500 mM 蔗糖的 0.1 U/mL 变形链球菌变异蔗糖酶显示出 97% 的抑制活性。它表现出竞争性抑制，Ki 值为 1.1 ± 0.2 mM，IC50 为 2.3 mM。根据分子对接分析，其抑制活性归因于疏水性和氢键相互作用。 Ru 作为抑菌剂抑制变形链球菌的生长，MIC 和 MBC 值分别为 6 mM 和 8 mM。此外，Ru与姜黄素结合时表现出协同抗菌活性。因此，Ru是一种天然的抗龋齿剂，具有抗变异蔗糖酶活性和对变异链球菌的抗菌活性。

  DOI：

  10.1007/s12257-018-0408-0

文献信息

• Synthesis and Sensory Evaluation of ent-Kaurane Diterpene Glycosides
  作者：Indra Prakash、Mary Campbell、Rafael Ignacio San Miguel、Venkata Sai Prakash Chaturvedula

  DOI：10.3390/molecules17088908

  日期：——

  rubusoside, stevioside, and rebaudioside-A has been carried out using Pd(OH)₂ and their corresponding dihydro derivatives have been isolated as the products. Synthesis of reduced steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR spectral data and chemical studies. Also, we report herewith the sensory evaluation of all the

  已使用 Pd(OH) 2 对从甜叶菊中分离出的三种对映贝壳杉烷二萜糖苷，即红花心甙、甜菊甙和莱鲍迪甙-A 进行催化氢化，并已分离出它们相应的二氢衍生物作为产物。还原型甜菊糖苷的合成使用简单的化学方法进行，其结构基于 1D 和 2D NMR 光谱数据和化学研究进行表征。此外，我们在此报告了所有还原化合物相对于它们相应的原始甜菊糖苷和蔗糖对这些分子的甜味特性的感官评价。
• [EN] NATURAL AND SYNTHETIC DITERPENE GLYCOSIDES, COMPOSITIONS AND METHODS<br/>[FR] GLYCOSIDES DITERPÉNIQUES NATURELS ET SYNTHÉTIQUES, COMPOSITIONS ET PROCÉDÉS
  申请人：COCA COLA CO

  公开号：WO2019147617A1

  公开（公告）日：2019-08-01

  Novel diterpene glycosides isolated from Stevia extract as well as diterpene glycosides that are synthetically prepared are provided herein. Compositions and consumables comprising the novel diterpene glycosides are also provided herein. Methods of enhancing the sweetness and/or flavor of consumables using the novel diterpene glycosides, methods of preparing compositions and consumables comprising the novel diterpene glycosides, methods of purifying the novel diterpene glycosides and methods of synthesizing the diterpene glycosides are also provided.

  本文提供了从甜菊提取物中分离出的新型二萜苷和合成制备的二萜苷。本文还提供了包含这些新型二萜苷的组合物和消费品。还提供了使用这些新型二萜苷增强消费品的甜味和/或风味的方法，制备包含这些新型二萜苷的组合物和消费品的方法，纯化这些新型二萜苷的方法以及合成二萜苷的方法。
• [EN] PRODUCTION OF STEVIOL GLYCOSIDES IN RECOMBINANT HOSTS<br/>[FR] PRODUCTION DE GLYCOSIDES DE STÉVIOL DANS DES HÔTES DE RECOMBINAISON
  申请人：EVOLVA SA

  公开号：WO2016120486A1

  公开（公告）日：2016-08-04

  The invention relates to recombinant microorganisms and methods for producing steviol glycosides, glycosylated ent-kaurenol, and glycosylated ent-kaurenoic acid.

  这项发明涉及重组微生物和生产叶草甙、糖基化的ent-kaurenol和糖基化的ent-kaurenoic酸的方法。
• [EN] METHODS FOR PREPARING REBAUDIOSIDE I AND USES<br/>[FR] PROCÉDÉS DE PRÉPARATION DE RÉBAUDIOSIDE I ET UTILISATIONS ASSOCIÉES
  申请人：COCA COLA CO

  公开号：WO2016028899A1

  公开（公告）日：2016-02-25

  Methods of preparing rebaudioside I, including highly purified rebaudioside I, are described herein. The methods utilize biocatalysts for converting rebaudioside A to rebaudioside I. Compositions and consumables comprising rebaudioside I, including sweetener compositions and flavor enhancing composition, are also provided.

  本文描述了制备鲜叶甙I的方法，包括高度纯化的鲜叶甙I。这些方法利用生物催化剂将鲜叶甙A转化为鲜叶甙I。还提供了包含鲜叶甙I的组合物和消费品，包括甜味剂组合物和增香组合物。
• [EN] HIGH-PURITY STEVIOL GLYCOSIDES<br/>[FR] GLYCOSIDES DE STÉVIOL DE GRANDE PURETÉ
  申请人：PURECIRCLE SDN BHD

  公开号：WO2014193888A1

  公开（公告）日：2014-12-04

  Methods of preparing highly purified steviol glycosides, particularly rebaudiosides A, D and M are described. The methods include utilizing recombinant microorganisms for converting various staring compositions to target steviol glycosides. In addition, novel steviol glycosides reb D2 and reb M2 are disclosed, as are methods of preparing the same. The highly purified rebaudiosides are useful as non-caloric sweetener in edible and chewable compositions such as any beverages, confectioneries, bakery products, cookies, and chewing gums.

  描述了制备高度纯化的甜菊糖苷方法，特别是A、D和M型再黄甜菊苷。这些方法包括利用重组微生物将不同的起始成分转化为目标甜菊糖苷。此外，还披露了新型甜菊糖苷reb D2和reb M2，以及其制备方法。这些高度纯化的再黄甜菊苷可用作无热量甜味剂，用于可食用和可咀嚼的组合物，如任何饮料、糖果、烘焙产品、饼干和口香糖。