18β-Glycyrrhetinic Acid 18β-甘草次酸

CAS 471-53-4 MFCD00003706

化学结构图

471-53-4
SMILES: CC1(C)[C@@H](O)CC[C@@]2(C)[C@H]1CC[C@]1(C)[C@@H]2C(=O)C=C2[C@@H]3C[C@@](C)(C(=O)O)CC[C@]3(C)CC[C@]21C

化学属性

Mol. FormulaC30H46O4
Mol. Weight470.68
Density1.14
Melting Point292-295°C
Solubility可溶 IN ACETIC ACID
Appearance 由甘草酸-ff两个分子的葡萄糖醛酸组成的苷。白色结晶性粉末，味甜，甜度约为蔗糖的200倍。其甜味与蔗糖等甜味剂不同，入口后要略过片刻才有甜味感，但留存时间长。少量甘草苷与蔗糖并用可少用20%蔗糖而甜度不变。虽无香气，但有增香效能。熔点(分解)220℃。水溶液呈弱酸性，可由酸的作用
Refractive index162 ° (C=1, MeOH)
Boiling Point588.3°C at 760 mmHg

别名和识别编码

Chemical Name18β-Glycyrrhetinic Acid
CAS Number471-53-4
Synonym ######## (2S,4AS,6AS,6BR,8AR,10S,12AS,12BR,14BR)-10-HYDROXY-2,4A,6A,6B,9,9,12A-HEPTAMETHYL-13-OXO-1,2,3,4,4A,5,6,6A,6B,7,8,8A,9,10,11,12,12A,12B,13,14B-ICOSAHYDRO-PICENE-2-CARB (3b,20b)-3-羟基-11-氧代-齐墩果-12-烯-29-酸,18β-甘草次酸 (3beta,18alpha,20beta)-3-Hydroxy-11-oxoolean-12-en-29-oic acid 12, Po 18-beta-Glycyrrhetinic acid 18-beta-Glycyrrhetinic acid; 3b-Hydroxy-11-oxo-18b,20b-olean-12-en 18-β-Glycyrrhetinsäure 18B-GLYCYRRHETINIC ACID 18Beta-glycyrrhetinic acid 18β-Glycyrrhetic acid 18β-Glycyrrhetinic acid {SNA} 18β-甘草次酸 3 3-Glycyrrhetinic acid 3-Hydroxy-11-oxoolean-12-en-29-säure, (3β,20β)- 3-beta-Hydroxy-11-oxoolean-12-en-3 3-beta-hydroxy-11-oxo-olean-12-en-30-oicaci 3B-HYDRO {} {uni_hamburg} 18β-Glycyrrhtinic a
EC Number207-444-6
Beilstein Registry Number2229654
MDL NumberMFCD00003706
PubChem Substance ID87570347
Reaxys-RN2229654
Merck Number3590
Chemical Name Translation18β-甘草次酸
Wiswesser Line NotationL F6 E6 B666 CV DUTJ A1 HVQ H1 K1 N1 O1 S1 S1 TQ-ALPHA
LabNetwork Molecule IDLN00839314
InChIInChI=1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1
Canonical SMILESCC1(C)[C@@H](O)CC[C@]([C@@]1([H])CC[C@@]([C@@]2(CC[C@]3(CC[C@](C(O)=O)(C[C@]3(C2=C4)[H])C)C)C)5C)(C)[C@@]5([H])C4=O
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分类

  • {uni_hamburg}
  • {SNA} Analytical Standards, EP Standards, EP Standards E - F, Pharmacopeia Metrological Institutes Standards, 分析/色谱
  • Heterocycles
  • {SNA} Asymmetric Synthesis,
  • {Chemicalbook} 食品添加剂: 调味剂（风味增强剂）: 甜味剂
  • {SNA} Analytical Standards, Chromatography, EP Standards, EP Standards E - F, Pharmaceutical Standards, Pharmacopeia Standards, 分析/色谱
  • {SNA} Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks,
  • Chiral Reagents
  • {SNA} Analytical Standards, Analytical/Chromatography, Chromatography, EP Standards, EP Standards E - F, Pharmaceutical Standards, Pharmacopeia Standards
  • Pharmaceuticals
  • Intermediates & Fine Chemicals
  • {SNA} Asymmetric Synthesis, Chemical Synthesis, Chiral Building Blocks,

产品应用

  • The aglycone of the triterpenoid Glyccyrrhizic acid.

相关文献及参考

  • [2]. Zhou J, et al. 18β-glycyrrhetinic acid suppresses experimental autoimmune encephalomyelitis through inhibition of microglia activation and promotion of remyelination. Sci Rep. 2015 Sep 2;5:13713.
  • [3]. Yang G, et al. Protective Effect of 18β-Glycyrrhetinic Acid against Triptolide-Induced Hepatotoxicity in Rats. Evid Based Complement Alternat Med. 2017;2017:3470320.
  • Carmichael, J., et al.: Cancer Res., 47, 943 (1987),
  • Deschesnes, R., et al.: J. Pharmacol. Exp. Ther., 320, 853 (2007),
  • Merck: 14,3590
  • Merck: 14,3590 Beilstein:10(3)4392
  • Short: EINECS
  • Short: III/5b
  • [1]. Huang RY, et al. 18β-Glycyrrhetinic acid suppresses cell proliferation through inhibiting thromboxane synthase in non-small cell lung cancer. PLoS One.
  • [1]. Huang RY, et al. 18β-Glycyrrhetinic acid suppresses cell proliferation through inhibiting thromboxane synthase in non-small cell lung cancer. PLoS One. 2014 Apr 2;9(4):e93690.

安全信息

Signal word Warning
GHS Symbol
WGK Germany3
Safety Statements
  • S22 Do not breathe dust 不要吸入粉尘；
  • S24/25 Avoid contact with skin and eyes 避免皮肤和眼睛接触；
  • S26 In case of contact with eyes, rinse immediately with plenty of water and seek medical advice 眼睛接触后，立即用大量水冲洗并征求医生意见；
  • S36/37/39 Wear suitable protective clothing, gloves and eye/face protection 穿戴适当的防护服、手套和眼睛/面保护；
Risk Statements
  • R22 Harmful if swallowed 吞咽有害
  • R36 Irritating to eyes 刺激眼睛
  • R36/37/38 Irritating to eyes, respiratory system and skin 对眼睛、呼吸系统和皮肤有刺激性
Precautionary statements
  • P264 Wash hands thoroughly after handling. 处理后要彻底洗净双手。
  • P270 Do not eat, drink or smoke when using this product. 使用本产品时不要吃东西，喝水或吸烟。
  • P280 Wear protective gloves/protective clothing/eye protection/face protection. 戴防护手套/防护服/眼睛的保护物/面部保护物。
  • P301+P312
  • P305+P351+P338
  • P330 Rinse mouth. 漱口
  • P337+P313
  • P501 Dispose of contents/container to..… 处理内容物/容器.....
Hazard statements
  • H302 Harmful if swallowed 吞食有害
  • H319 Causes serious eye irritation 严重刺激眼睛
Personal Protective Equipment dust mask type N95 (US), Eyeshields, Gloves
RTECSRK0180000
Hazard Codes Xn 
TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intraperitoneal
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 308 mg/kg
TOXIC EFFECTS :
   Details of toxic effects not reported other than lethal dose value
REFERENCE :
   NIIRDN Drugs in Japan (Ethical Drugs).  (Yakugyo Jiho Co., Ltd., Tokyo,
   Japan)  Volume(issue)/page/year: -,319,1990

TYPE OF TEST            : LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE       : Intravenous
SPECIES OBSERVED        : Rodent - mouse
DOSE/DURATION           : 56 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#02067

Storage condition 2-8°C

其他信息

  • 甘草次酸价格(试剂级):更新日期 产品编号 产品名称 包装 价格 2014/06/02 G0149 甘草次酸 Glycyrrhetic Acid 25G 1410元 2014/06/02 G0149 甘草次酸 Glycyrrhetic Acid 1G 185元 2010/06/21 120150050 甘草次酸 18-beta-Glycyrrhetinic acid 98+% 5 GR 735元
  • 图谱信息:甘草次酸(471-53-4)红外图谱(IR1) 甘草次酸(471-53-4)核磁图( 13 CNMR) 甘草次酸(471-53-4)红外图谱(IR2)
  • Acros Organics:甘草次酸 18-beta-Glycyrrhetinic acid, 98+%(471-53-4)
  • 18 β-Glycyrrhetinic Acid is an aglycone of the triterpenoid Glyccyrrhizic acid, which is found in liquorice. inhibits the PGDH (15-hydroxyprostaglandin dehydrogenase) leading to increased prostaglandin concentration in the digestive system. Also investigated for potential antibiotic activities.
  • 参考质量标准:中国企标 水分 ≤13% 灰分 ≤15% 熔点 220℃
  • 比旋光度:165 ° (c=1, CHCl3,on dry ba)
  • 上游原料:乙醇 --> 乙醇溶液 --> 蔗糖 --> 甘草酸 --> 甘草 --> SIS --> 甘草酸三铵盐
  • 方法二:由豆科植物基草（Glycyrrhiza uralen-sis fisch）的根茎中提取的甘草酸，制成铵盐后再经水解而得。甘草为我年生草本，主产于内蒙古和甘肃等地。甘草的根及根茎主要含甘草甜素，为甘草酸（Glycyrrhiz-ic acid）的钾、钙盐，是甘草的甜味成分。甜约为蔗糖的50倍。将粉碎后的甘草加水加热，连续逆流提取，分离除去草渣杂质，得水溶液。蒸发、浓缩，搅拌下加硫酸pH2-3。静置沉淀，除去上清液。沉淀物用水洗尽硫酸根，加热浓缩浓缩，熬制成甘草酸膏。将甘草酸膏粉碎，用95%乙醇加流提取2-3次，每次3h，得乙醇溶液。经过滤后搅拌通氨至pH为7-7.5。再过滤，得甘草酸三铵盐粗品，用冰醋酸精制，即为米黄色的甘草酸单铵盐。将甘草酸单铵盐加入5%硫酸水溶液中，搅拌加热至近沸，回流水解15h，过滤、水洗得甘草次酸粗品。经重结晶、脱色即得含量在92%以上的基草次酸。以甘草计，总收率约0.5%。
  • MOL 文件:471-53-4.mol
  • 用途二:抗生素类药，用于治疗葡萄球菌、链球菌、大肠杆菌、螺旋杆菌等的感染
  • 毒性:天然品，无毒。有解毒保肝作用。 LD 50 805mg/kg(小鼠，腹腔)。
  • Sigma Aldrich:471-53-4(sigmaaldrich)
  • 用途三:甜味剂；甜味改良剂；调味剂(与食盐配合应用，效果特别大)；香味增强剂(乳制品、可可制品、蛋制品、羊肉等除膻增香用)。我国民间惯用于酱及酱制品、腌渍品等。
  • MSDS 信息:18-beta-Glycyrrhetinic acid(471-53-4).msds
  • 用途四:该品为消炎药。用于治疗肾上腺皮质机能减退、胃及十二指肠溃疡等疾病。
  • 使用限量:GB 2760--1996：对甘草酸一钾、三钾的限量，同“02317，甘草”。
  • 用途一:是一种重要的医药和高档化妆品原料，具有抗炎抗过敏、抑制细菌繁殖等作用
  • TCI Shanghai:甘草次酸 Glycyrrhetic Acid,>;97.0%(T)(471-53-4)
  • 方法一:由甘草抽提液(见“02317甘草”)经浓缩、干燥后，制得粗结晶，然后在稀酒精中重结晶而得。得率6%-14% 也可直接用氨水萃取，经浓缩后用硫酸沉淀，再用95

系列性分类

  1. Chemical Synthesis 化学合成
  2. Building Blocks 合成砌块
  3. Organic Building Blocks 有机砌块
  1. Chemical Synthesis 化学合成
  2. Asymmetric Synthesis 不对称合成
  3. Chiral Building Blocks 手性分子砌块
  4. Complex Molecules - Chiral Building Blocks
  1. Life Science 生命科学
  2. Biochemistry / Glyco-Chemistry
  3. Terpenes
  1. Medical Research Areas
  2. Metabolism
  3. Endogenous Metabolite  (内源性代谢物)

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