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


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