10-姜酮醇 | 23513-15-7

• 物质功能分类: 生物化工 - 中草药成分
• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 10-姜酮醇
• 中文别名: 10-姜辣醇；(S)-5-羟基-1-(4-羟基-3-甲氧基苯基)十四烷-3-酮；[10]-姜酚；10-姜酚；1-姜酮醇
• 英文名称: (10)-Gingerol
• 英文别名: (5S)-5-hydroxy-1-(4-hydroxy-3-methoxyphenyl)tetradecan-3-one
• CAS: 23513-15-7
• 化学式: C₂₁H₃₄O₄
• mdl: MFCD01682694
• 分子量: 350.499
• InChiKey: AIULWNKTYPZYAN-SFHVURJKSA-N

物化性质

• 熔点：
  56-58 °C
• 沸点：
  499.7±35.0 °C(Predicted)
• 密度：
  1.037±0.06 g/cm3(Predicted)
• 闪点：
  166℃
• 溶解度：
  溶于甲醇：5mg/mL，透明，无色
• LogP：
  4.900 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 安全说明：
  S24/25
• 危险类别码：
  R53
• WGK Germany：
  3
• 海关编码：
  2914509090
• 危险性防范说明：
  P264,P270,P273,P301+P312+P330,P501
• 危险性描述：
  H302,H413
• 储存条件：
  2-8°C

SDS

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Section 1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE
Product identifiers
Product name : [10]-Gingerol
CAS-No. : 23513-15-7
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 [EU-GHS/CLP]
Chronic aquatic toxicity (Category 4)
This substance is not classified as dangerous according to Directive 67/548/EEC.
Label elements
Labelling according Regulation (EC) No 1272/2008 [CLP]
Pictogram none
Signal word none
Hazard statement(s)
H413 May cause long lasting harmful effects to aquatic life.
Precautionary statement(s) none
Supplemental Hazard none
Statements
Other hazards - none

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Section 3. COMPOSITION/INFORMATION ON INGREDIENTS
Substances
Synonyms : 10-Gingerol
(S)- 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone
Formula : C21H34O4
Molecular Weight : 350,49 g/mol
Component Concentration
(S)- 5-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)-3-tetradecanone
CAS-No. 23513-15-7 -

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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
Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation.
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.
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: 2 - 8 °C
Specific end use(s)
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
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 with lumps
Colour: light yellow
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 499,7 °C at 1.013 hPa - lit.
boiling range
g) Flash point 166,3 °C - closed cup
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- log Pow: 5,035
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
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
LD50 Intraperitoneal - mouse - > 100 mg/kg
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
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

简介

研究表明，生（干）姜的主要活性成分为挥发油和10-姜酮醇。10-姜酮醇是多种具有姜辣味的结构类似物质的总称，其结构中均含有3-甲氧基-4-羟基苯基官能团，主要包括姜酚类（Gingerols）、姜烯酚类（Shogals）、副姜油酮类（Paradols）、姜酮类（Zingerone）、姜二酮类（Gingerdiones）和姜二醇类（Gingerdiols），而姜酚是其主要成分。

药理作用

现代药理学研究发现，10-姜酮醇是生姜发挥药理作用和呈现预防保健效果的主要活性成分。其主要药理作用包括抗血小板聚集、升高血压与强心、降血脂、抗动脉粥样硬化、保护胃黏膜、防治溃疡、保肝利胆、镇痛、抗病毒、抗炎、抗惊厥、抗氧化、预防肿瘤、抗过敏、抗辐射和抗运动病等。因此，有充分的理由预期高含量高品质的10-姜酮醇将具有广阔的应用领域和巨大的市场需求。

用途

10-姜酮醇被观察到对脂类具有抗氧化作用，并能有效抑制肥胖及脂肪组织炎症。

化学性质

白色蜡状物质，可溶于甲醇、乙醇和DMSO等有机溶剂，来源于生姜。

用途

用于含量测定/鉴定/药理实验等。其药理药效包括止呕、强心、降压、降血脂、抗血小板聚集、抗动脉粥样硬化、抗肿瘤、抗氧化、抗炎及解热镇痛等多种作用。[10]-姜酚是一种具有抗发炎和抗氧化活性的生物活性化合物。

反应信息

• 作为反应物：
  描述：

  10-姜酮醇 在 1,1-二苯-2-苦基肼 作用下， 以 甲醇 为溶剂， 生成 [10]-gingerol 6,6’ dimer
  参考文献：
  名称：

  植物酚二聚反应：从基本规则到非对映选择性及其他

  摘要：

  植物酚二聚化是一种自由基介导的偶联反应，在包括木质素生物合成在内的许多领域发挥着关键作用。为了了解该反应，使用 2,2-二苯基-1-苦基肼自由基在甲醇中引发一系列植物酚二聚反应。使用超高效液相色谱结合电喷雾四极杆飞行时间串联质谱 (UHPLC-ESI-Q-TOF-MS/MS) 原位分析对产物进行鉴定。鉴定出的产品主要有联苯酚、厚朴酚、和厚朴酚、姜酚6,6'-二聚体、3,6-二甲氧基儿茶酚β,β'二聚体、大戟红素、双丁香酚、脱氢二异丁香酚、反式-ε-葡萄素、(+)松脂醇、 (-) 松脂醇。结构-功能关系分析允许定义四个基本规则：间位排除、C-C 键合优势、邻-diOH 共激活和环外 C=C 参与。然而，环外 C=C 的参与需要与酚核心和对位共轭。-OH 基团的 - 位点，产生具有两个手性中心的呋喃稠合二聚体。计算化学表明，整个过程是通过自由基偶联反应和分子内共轭加成反应完成的。对于辣根过氧化物酶

  DOI：

  10.3390/molecules27154842
• 作为产物：
  描述：

  3-(4-羟基-3-甲氧基苯基)丙酸 在 吡啶 、 chromium(VI) oxide 、 lithium aluminium tetrahydride 、 硫酸 、 三氟化硼乙醚 、 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 、 对甲苯磺酸 、 calcium carbonate 、 碘甲烷 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 二氯甲烷 、 氯仿 、 水 、 乙腈 为溶剂， 反应 37.0h， 生成 10-姜酮醇
  参考文献：
  名称：

  Total synthesis of natural gingerols, the three active principles of ginger

  摘要：

  Natural gingerols, (+)(S)[6]-, (+)(S)[8]-, and (+)(S)[10]-gingerols, the three active principles of ginger, have been prepared from a common optically active intermediate 9 which was readily made by asymmetric synthesis from a chiral beta-keto sulfoxide 5.

  DOI：

  10.1021/jo00060a038

文献信息

• An enantioselective synthesis of (+)-(S)-[n]-gingerols via the l-proline-catalyzed aldol reaction
  作者：Shichao Ma、Shilei Zhang、Wenhu Duan、Wei Wang

  DOI：10.1016/j.bmcl.2009.03.081

  日期：2009.7

  An enantioselective approach to (+)-(S)-[n]-gingerols (1a–c) has been developed. The requisite stereogenic centers of target molecules are facilely constructed by the proline-catalyzed cross-aldol reaction from readily available achiral starting materials.

  对（+）-（S）-[ n ]-姜酚（1a – c）的对映选择性方法已经开发出来。靶分子的必需立体异构中心是由脯氨酸催化的交叉羟醛缩合反应轻松地从容易获得的非手性原料中构建的。
• Kinetic Resolution of β-Hydroxy Carbonyl Compounds via Enantioselective Dehydration Using a Cation-Binding Catalyst: Facile Access to Enantiopure Chiral Aldols
  作者：Sushovan Paladhi、In-Soo Hwang、Eun Jeong Yoo、Do Hyun Ryu、Choong Eui Song

  DOI：10.1021/acs.orglett.8b00547

  日期：2018.4.6

  β-hydroxy carbonyl (aldol) compounds through enantioselective dehydration process was developed using a cation-binding Song’s oligoethylene glycol (oligoEG) catalyst with potassium fluoride (KF) as base. A wide range of racemic aldols was resolved with extremely high selectivity factors (s = up to 2393) under mild reaction conditions. This protocol is easily scalable. It provides an alternative approach for

  通过使用阳离子结合的宋氏低聚乙二醇（oligoEG）催化剂，以氟化钾（KF）为基础，开发了通过对映选择性脱水过程开发的外消旋β-羟基羰基（aldol）化合物的实用且高度对映选择性的非酶动力学拆分方法。在温和的反应条件下，极高的选择性因子（s =高达2393）可分离出多种外消旋醇醛。该协议易于扩展。它为合成对映体纯形式的多种生物学和药学上相关的手性醇醛提供了另一种方法。例如，外消旋姜醇可以以极高的效率（s> 240），在一个步骤中同时提供对映体纯的姜黄醇和相应的Shogaols。这种动力学拆分过程的显着效果可归因于在由手性催化剂，底物和KF产生的密闭超分子手性笼中的系统协同氢键催化。
• [EN] GINGEROL COMPOUNDS AND THEIR USE AS FLAVOR MODIFIERS<br/>[FR] COMPOSÉS DE GINGÉROL ET LEUR UTILISATION EN TANT QUE MODIFICATEURS D'ARÔME
  申请人：FIRMENICH & CIE

  公开号：WO2021094268A1

  公开（公告）日：2021-05-20

  The present disclosure relates to gingerol compounds, whether in their diol form or as a derivative, and their use to enhance the salty taste or the umami taste of a flavored article. The disclosure also provides compositions and flavored products containing such compounds. In some embodiments, the flavored products have reduced amounts of salt or umami-enhancing compounds (glutamates, arginates, purinic ribonucleotides, such as inosine monophosphate (IMP) and guanosine monophosphate (GMP)), relative to comparable flavored products that do not incorporate the gingerol compounds. The disclosure further provides methods of making monoacetate or diacetate derivatives of gingerol diols.

  本公开涉及姜酚化合物，无论是以它们的二醇形式还是作为衍生物，并且它们的用途是增强调味品的咸味或鲜味。该公开还提供了含有这些化合物的组合物和调味产品。在某些实施例中，相对于不含姜酚化合物的类似调味产品，这些调味产品的盐或鲜味增强化合物（谷氨酸盐、精氨酸盐、嘌呤核苷酸盐，例如肌苷酸酸（IMP）和鸟苷酸酸（GMP））的含量减少。该公开还提供制备姜酚二醇的单醋酸酯或双醋酸酯衍生物的方法。
• An Efficient Enantioselective Synthesis of Natural Gingerols, the Active Principles of Ginger
  作者：A. Ramesh Reddy、Sachin B. Wadavrao、J. S. Yadav、A. Venkat Narsaiah

  DOI：10.1002/hlca.201400393

  日期：2015.7

  A straightforward synthesis of (S)‐gingerols 1–3 has been described. The requisite stereogenic center in the target molecules was introduced by Sharpless asymmetric dihydroxylation using a chiral complex, AD‐mix β. This route is simple and efficient to prepare the products in very good yields.

  （的一种直接合成小号）-gingerols 1 - 3进行了说明。使用手性复合物AD- mixβ，通过Sharpless不对称二羟基化作用在靶分子中引入必要的立体异构中心。这条路线简单高效，可以非常好地制备产品。
• Myricanol Derivatives and Uses Thereof for Treatment of Neurodegenerative Diseases
  申请人：UNIVERSITY OF SOUTH FLORIDA

  公开号：US20150051294A1

  公开（公告）日：2015-02-19

  The subject invention pertains to myricanol derivatives, therapeutic compositions, and methods for treatment of neurodegenerative diseases, in particular, neurodegenerative diseases associated with abnormal accumulation of protein tau.

  本发明涉及myricanol衍生物、治疗组合物和治疗神经退行性疾病的方法，特别是与蛋白质tau异常积累相关的神经退行性疾病的治疗方法。