1449-05-4

• 常用中文名：甘草次酸(α型)
• 常用英文名：Glycyrrhetinic acid
• CAS号：1449-05-4
• 分子式：C₃₀H₄₆O₄
• 分子量：470.684
• 相关类别： 生物化工 植物提取物
• 发布时间：2018-08-16 12:58:46
• 更新时间：2024-01-03 16:33:14
• 18α-Glycyrrhetinic acid,一种饮食衍生的化合物,是 NF-kB 的抑制剂和蛋白酶体 (proteasome) 的激活剂,在多细胞生物中起到促进长寿和抗聚集因子的作用。18α-Glycyrrhetinic acid 诱导细胞凋亡。

名称

• 中文名: 18α-甘草次酸
• 英文名: glycyrrhetinate
• 中文别名: 18-ALFA-甘草次酸; 甘草次酸(α型); 甘草次酸
• 英文别名: 18a-Glycyrrhetic acid; (3β,18α)-3-Hydroxy-11-oxoolean-12-en-29-oic acid; 18a-Glycyrrhetinic acid; MFCD00064897; Olean-12-en-29-oic acid, 3-hydroxy-11-oxo-, (3β,18α)-; Glycyrrhetinic acid; EINECS 215-907-9

物化性质

• 密度: 1.1±0.1 g/cm3
• 沸点: 588.3±50.0 °C at 760 mmHg
• 熔点: 331-333°C
• 分子式: C₃₀H₄₆O₄
• 分子量: 470.684
• 闪点: 323.7±26.6 °C
• 精确质量: 470.339600
• PSA: 74.60000
• LogP: 6.57
• 蒸汽压: 0.0±3.7 mmHg at 25°C
• 折射率: 1.563
• 储存条件:

  保持贮藏器密封、储存在阴凉、干燥的地方，确保工作间有良好的通风或排气装置

• 稳定性:

  如果遵照规格使用和储存则不会分解，未有已知危险反应，避免氧化物

• 分子结构:

  1、 摩尔折射率：133.69

  2、 摩尔体积（cm³/mol）：411.6

  3、 等张比容（90.2K）：1082.2

  4、 表面张力（dyne/cm）: 47.7

  5、 介电常数：无可用

  6、 偶极距（10^-24cm³）：无可用

  7、 极化率：52.99

• 计算化学:

  1、 疏水参数计算参考值（XlogP）：6.4

  2、 氢键供体数量：2

  3、 氢键受体数量：4

  4、 可旋转化学键数量：1

  5、 互变异构体数量：5

  6、 拓扑分子极性表面积（TPSA）：74.6

  7、 重原子数量：34

  8、 表面电荷：0

  9、 复杂度：965

  10、 同位素原子数量：0

  11、 确定原子立构中心数量：8

  12、 不确定原子立构中心数量：1

  13、 确定化学键立构中心数量：0

  14、 不确定化学键立构中心数量：0

  15、 共价键单元数量：1

• 更多:

  1. 性状：未确定。

  2. 密度（g/mL,25/4℃）： 未确定

  3. 相对蒸汽密度（g/mL,空气=1）：未确定

  4. 熔点（ºC）：331-333

  5. 沸点（ºC,常压）：未确定

  6. 沸点（ºC,5.2kPa）： 未确定

  7. 折射率： 未确定

  8. 闪点（ºC）： 未确定

  9. 比旋光度（º）： 未确定

  10. 自燃点或引燃温度（ºC）： 未确定

  11. 蒸气压（kPa,25ºC）： 未确定

  12. 饱和蒸气压（kPa,60ºC）： 未确定

  13. 燃烧热（KJ/mol）：未确定

  14. 临界温度（ºC）： 未确定

  15. 临界压力（KPa）： 未确定

  16. 油水（辛醇/水）分配系数的对数值： 未确定

  17. 爆炸上限（%,V/V）：未确定

  18. 爆炸下限（%,V/V）： 未确定

  19. 溶解性：未确定

生物活性

• 描述: 18α-Glycyrrhetinic acid,一种饮食衍生的化合物,是 NF-kB 的抑制剂和蛋白酶体 (proteasome) 的激活剂,在多细胞生物中起到促进长寿和抗聚集因子的作用。18α-Glycyrrhetinic acid 诱导细胞凋亡。
• 相关类别:
  信号通路 >> 细胞凋亡 >> 细胞凋亡
  研究领域 >> 癌症
  研究领域 >> 炎症/免疫
  信号通路 >> 代谢酶/蛋白酶 >> 蛋白酶体
  研究领域 >> 神经疾病
• 靶点:

  NF-κB

  Proteasome

• 体外研究: 18α-甘草次酸(18a-GA)分别在治疗48小时和72小时后显着降低LX-2细胞数14.8％和31.2％(P <0.05)。与对照组相比,18α-甘草次酸在G0/G1期也显著增加LX-2细胞的百分比,并在处理48小时和72小时后在S期降低。18α-甘草次酸在48h时使细胞凋亡增加至6.8%,与对照组(2.5%)相比,72h时LX-2细胞凋亡率分别为3.1%和15.6%(P<0.01)。此外,18α-甘草次酸诱导PPAR-γ的表达并改变一些细胞周期和凋亡相关蛋白。18α-甘草次酸也抑制NF-κB DNA结合活性[1]。
• 体内研究: 18α-甘草次酸(18α-GA)处理显著提高秀丽隐杆线虫菌株的寿命,最有效浓度为20μg/mL。结果显示,18α-甘草次酸处理可显著延迟麻痹。18α-甘草次酸处理也使Aβ沉积显著减少[2]。
• 细胞实验: 为了测定细胞周期，将每孔5×105个细胞接种到6孔板上，并在完全生长培养基（DMEM+10％FBS）中孵育过夜。饥饿24小时后，随后用含有或不含有18α-甘草次酸（18a-GA）的10％FBS刺激细胞。18α-甘草次酸的最终浓度为8.0mM。将细胞分别孵育24小时、48小时和72小时，然后进行流式细胞术分析。流式细胞术分析一式三份。用18α-甘草次酸处理后，对细胞进行染色，然后通过流式细胞术测量细胞凋亡状态[1]。
• 动物实验: 本研究使用秀丽隐杆线虫菌株。将同步L4幼虫CL2006动物（每种条件100至120只动物）在20℃下转移到含有18α-甘草次酸（18α-GA）或DMSO的线虫生长培养基（NGM）平板上。将同步CL4176动物（每种条件150至300只动物）转移到含有在16°C下将18α-甘草次酸或DMSO加热48小时，然后升温至25°C进行转基因诱导。在CL2006菌株的成年第1天和CL4176菌株升温后24小时开始对瘫痪动物进行评分。每次瘫痪试验至少重复三次。如果线虫头部周围出现清除的细菌晕圈，或者在刺激时无法进行半端体波传播，则线虫被评为瘫痪[2]。
• 参考文献:

  [1]. Zong L et al. 18α-glycyrrhetinic acid extracted from Glycyrrhiza radix inhibits proliferation and promotes apoptosis of the hepatic stellate cell line. J Dig Dis. 2013 Jun;14(6):328-36.

  [2]. Papaevgeniou N, et al. 18α-Glycyrrhetinic Acid Proteasome Activator Decelerates Aging and Alzheimer's Disease Progression in Caenorhabditis elegans and Neuronal Cultures. Antioxid Redox Signal. 2016 Dec 1;25(16):855-869.

MSDS

Section1. IDENTIFICATION OF THE SUBSTANCE/MIXTURE Product identifiers : 18α-Glycyrrhetinic acid Product name CAS-No.: 1449-05-4 Relevant identified uses of the substance or mixture and uses advised against Identified uses: Laboratory chemicals, Manufacture of substances Section2. HAZARDS IDENTIFICATION Classification of the substance or mixture Classification according to Regulation (EC) No 1272/2008 [EU-GHS/CLP] Acute toxicity, Oral (Category 4) Classification according to EU Directives 67/548/EEC or 1999/45/EC Harmful if swallowed. Label elements Labelling according Regulation (EC) No 1272/2008 [CLP] Pictogram Signal wordWarning Hazard statement(s) H302Harmful if swallowed. Precautionary statement(s) none Supplemental Hazardnone Statements According to European Directive 67/548/EEC as amended. Hazard symbol(s) R-phrase(s) R22Harmful if swallowed. S-phrase(s)none Other hazards - none Section3. COMPOSITION/INFORMATION ON INGREDIENTS Substances : 3β-Hydroxy-11-oxo-18α,20β-olean-12-en-29-oic acid Synonyms Formula: C30H46O4 Molecular Weight: 470,68 g/mol ComponentConcentration (3β,18α,20β)-3-Hydroxy-11-oxoolean-12-en-29-oic acid CAS-No.1449-05-4- EC-No.215-907-9 Section4. 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 Overexposure can cause sodium retention and potassium loss leading to hypertension, water retention, and electrolyte imbalance. Indication of any immediate medical attention and special treatment needed no data available Section5. 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 Section6. ACCIDENTAL RELEASE MEASURES Personal precautions, protective equipment and emergency procedures Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. 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. Section7. HANDLING AND STORAGE Precautions for safe handling Avoid contact with skin and eyes. 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. Specific end uses no data available Section8. 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 Safety glasses with side-shields conforming to EN166 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 Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Respiratory protection For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU). Section9. PHYSICAL AND CHEMICAL PROPERTIES Information on basic physical and chemical properties a) AppearanceForm: solid b) Odourno data available c) Odour Thresholdno data available d) pHno data available e) Melting point/freezingno data available point f) Initial boiling point and no data available boiling range g) Flash pointno data available h) Evaporation rateno data available i) Flammability (solid, gas) no data available j) Upper/lowerno data available flammability or explosive limits k) Vapour pressureno data available l) Vapour densityno data available m) Relative densityno data available n) Water solubilityno data available o) Partition coefficient: n- no data available octanol/water p) Autoignitionno data available temperature q) Decompositionno data available temperature r) Viscosityno data available s) Explosive propertiesno data available t) Oxidizing propertiesno data available Other safety information no data available Section10. 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, Strong bases Hazardous decomposition products Other decomposition products - no data available Section11. TOXICOLOGICAL INFORMATION Information on toxicological effects Acute toxicity LD50 Oral - mouse - 560 mg/kg Remarks: Behavioral:Change in motor activity (specific assay). Gastrointestinal:Other changes. 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 InhalationMay be harmful if inhaled. May cause respiratory tract irritation. IngestionHarmful if swallowed. Skin May be harmful if absorbed through skin. May cause skin irritation. EyesMay cause eye irritation. Signs and Symptoms of Exposure Overexposure can cause sodium retention and potassium loss leading to hypertension, water retention, and electrolyte imbalance. Additional Information RTECS: RK0190000 Section12. 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 Section13. 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. Section14. 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: noIMDG Marine pollutant: noIATA: no Special precautions for user no data available Section15. 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 Section16. 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.

毒性和生态

毒理学数据: 急性毒性：小鼠口经LD50：560mg/kg；小鼠腹经LD50：455mg/kg；小鼠静脉LD50：100mg/kg 生态学数据: 对是水稍微有危害的不要让未稀释或大量的产品接触地下水、水道或者污水系统，若无政府许可，勿将材料排入周围环境。 CHEMICAL IDENTIFICATION RTECS NUMBER : RK0190000 CHEMICAL NAME : 18-alpha-Olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo- CAS REGISTRY NUMBER : 1449-05-4 LAST UPDATED : 199612 DATA ITEMS CITED : 3 MOLECULAR FORMULA : C30-H46-O4 MOLECULAR WEIGHT : 470.76 WISWESSER LINE NOTATION : L F6 E6 B666 CV DUTJ A1 HVQ H1 K1 N1 O1 S1 S1 TQ -BETA HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 560 mg/kg TOXIC EFFECTS : Behavioral - changes in motor activity (specific assay) Gastrointestinal - other changes REFERENCE : CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 28,3449,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intraperitoneal SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 455 mg/kg TOXIC EFFECTS : Behavioral - changes in motor activity (specific assay) Gastrointestinal - other changes REFERENCE : CPBTAL Chemical and Pharmaceutical Bulletin. (Japan Pub. Trading Co., USA, 1255 Howard St., San Francisco, CA 94103) V.6- 1958- Volume(issue)/page/year: 28,3449,1980 TYPE OF TEST : LD50 - Lethal dose, 50 percent kill ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : 100 mg/kg TOXIC EFFECTS : Details of toxic effects not reported other than lethal dose value REFERENCE : CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) Volume(issue)/page/year: NX#02068

安全

• 危害码 (欧洲): Xn: Harmful;
• 风险声明 (欧洲): R22
• 安全声明 (欧洲): S22-S23-S36/37/39
• WGK德国: 3
• RTECS号: RK0190000
• 海关编码: 2938909030

合成路线

471-53-4 ~46% 1449-05-4

文献：Ullah, Nisar; Seebacher, Werner; Haslinger, Ernst; Jurenitsch, Johann; Rauchensteiner, Katharina; Weis, Robert Monatshefte fur Chemie, 2002 , vol. 133, # 2 p. 139 - 150

650140-36-6 ~85% 1449-05-4

文献：Ignatov; Prokof'ev; Ipatova; Timofeev; Medvedeva; Misharin Russian Journal of Bioorganic Chemistry, 2003 , vol. 29, # 4 p. 390 - 394

上下游产品

上游产品  1
471-53-4
下游产品  0

海关

海关编码	2915900090
中文概述	2915900090. 其他饱和无环一元羧酸及其酸酐（酰卤、过氧）化物、过氧酸及其卤化、硝化、磺化、亚硝化衍生物. 增值税率:17.0%. 退税率:9.0%. 监管条件:AB(入境货物通关单,出境货物通关单). 最惠国关税:5.5%. 普通关税:30.0%
申报要素	品名, 成分含量, 用途
监管条件	A.入境货物通关单 B.出境货物通关单
检验检疫	R.进口食品卫生监督检验 S.出口食品卫生监督检验 M.进口商品检验 N.出口商品检验
Summary	2915900090 other saturated acyclic monocarboxylic acids and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:5.5% General tariff:30.0%