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471-53-4 分子结构
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(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-icosahydropicene-2-carboxylic acid

ChemBase编号:72941
分子式:C30H46O4
平均质量:470.68384
单一同位素质量:470.33960995
SMILES和InChIs

SMILES:
C1[C@@H](C([C@H]2[C@](C1)([C@@H]1[C@@](CC2)([C@]2(C(=CC1=O)[C@H]1[C@@](CC2)(CC[C@](C1)(C)C(=O)O)C)C)C)C)(C)C)O
Canonical SMILES:
O=C1C=C2[C@@H]3C[C@](C)(CC[C@]3(C)CC[C@]2([C@]2([C@H]1[C@@]1(C)CC[C@@H](C([C@@H]1CC2)(C)C)O)C)C)C(=O)O
InChI:
InChI=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
InChIKey:
MPDGHEJMBKOTSU-YKLVYJNSSA-N

引用这个纪录

CBID:72941 http://www.chembase.cn/molecule-72941.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(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-icosahydropicene-2-carboxylic acid
IUPAC传统名
jintan
(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-icosahydropicene-2-carboxylic acid
别名
甘草次酸
18β-甘草次酸
3β-Hydroxy-11-oxo-18β,20β-olean-12-en-29-oic acid
18β-Glycyrrhetinic acid
Enoxolone
(3β,20β)-3-Hydroxy-11-oxoolean-12-en-29-oic Acid
3β-Hydroxy-11-oxo-olean-12-en-30-oic Acid
18β-Glycyrrhetic Acid
18β-Glycyrrhetinic Acid
Biosone
GM 1658
Glycyrrhetinic acid
NSC 35347
PO 12
STX 352
Subglycyrrhelinic Acid
α-Glycyrrhetinic Acid
Glycyrrhetic Acid
(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-icosahydropicene-2-carboxylic acid
Glycyrrhetinate
Arthrodont
3β-Hydroxy-11-oxoolean-12-en-30-olic acid
Glycyrrhetinic acid
Enoxolone
Glycyrrhetin
Uralenic acid
Glycyrrhetic acid
Biogastrone acid
Rhetinic acid
Enoxolone
CAS号
471-53-4
EC号
207-444-6
MDL号
MFCD00003706
Beilstein号
2229654
PubChem SID
162037861
24873370
24895033
PubChem CID
10114
CHEBI ID
30853
ATC码
D03AX10
CHEMBL
230006
Chemspider ID
9710
维基百科标题
Glycyrrhetinic_acid

理论计算性质

理论计算性质

JChem
极化表面积 74.6 Å2 可自由旋转的化学键
里宾斯基五规则 false  Acid pKa 4.4443316 
质子受体 质子供体
LogD (pH = 5.5) 4.940498  LogD (pH = 7.4) 3.1778886 
Log P 6.031328  摩尔折射率 134.2685 cm3
极化性 53.29785 Å3

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
熔点
292-295 °C(lit.) expand 查看数据来源
比旋光度
[α]20/D +165±3°, c = 1% in chloroform expand 查看数据来源
[α]22/D +170.0°, c = 1 in chloroform expand 查看数据来源
保存条件
-20°C expand 查看数据来源
RTECS编号
RK0180000 expand 查看数据来源
欧盟危险性物质标志
有害性(Harmful) 有害性(Harmful) (Xn) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
22-36 expand 查看数据来源
安全公开号
22-24/25 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H302-H319 expand 查看数据来源
GHS警示性声明
P305 + P351 + P338 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
相关基因信息
human ... HSD11B1(3290), HSD11B2(3291)rat ... Hsd11b1(25116), Hsd11b2(25117) expand 查看数据来源
生物活性机理
Calcium-mobilizer in P815 cells in-vitro expand 查看数据来源
Reported to inhibit reactive oxygen species generation by human neutrophils in-vitro expand 查看数据来源
Reported to trap hydroxyl radicals to suppress rat liver injury caused by ischemia-perfusion expand 查看数据来源
纯度
≥97.0% (T) expand 查看数据来源
97% expand 查看数据来源
级别
purum expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
生物来源
Aglycone from Glycyrrhiza glabra and some other plants expand 查看数据来源
应用领域
Antibacterial, antitussive agent expand 查看数据来源
Antiinflammatory expand 查看数据来源
Used in treatment of noninfective inflammatory disorders (skin, mouth, etc.) expand 查看数据来源
Empirical Formula (Hill Notation)
C30H46O4 expand 查看数据来源

详细说明

详细说明

Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
Selleck Chemicals -  S2296 external link
Research Area: Inflammation
Biological Activity:
Enoxolone is a pentacyclic triterpenoid derivative of the beta-amyrin type obtained from the hydrolysis of glycyrrhizic acid, which was obtained from the herb liquorice.It inhibits the enzymes (15-hydroxyprostaglandin dehydrogenase and delta-13-prostaglandin) that metabolize the prostaglandins PGE-2 and PGF-2α to their respective 15-keto-13,14-dihydro metabolites which are inactive. This causes an increased level of prostaglandins in the digestive system. Prostaglandins inhibit gastric secretion but stimulate pancreatic secretion and mucous secretion in the intestines and markedly increase intestinal motility. [1]
Sigma Aldrich -  G10105 external link
包装
10, 25 g in poly bottle
Toronto Research Chemicals -  G735000 external link
An anti-inflammatory (topical).

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • http://en.wikipedia.org/wiki/Glycyrrhetinic_acid
  • Carmichael, J., et al.: Cancer Res., 47, 943 (1987)
  • Deschesnes, R., et al.: J. Pharmacol. Exp. Ther., 320, 853 (1987)
  • Yamaguchi, H., et al.: Biol. Pharm. Bull., 31, 1008 (1987)
  • Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 1057D, (ir)
  • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 596A, (nmr)
  • Beaton, J.M. et al., J.C.S., 1955, 3126, (synth)
  • Mer, J., Am. Perfum. Aromat., 1959, 74, 39, (isol)
  • U.K. Pat., 1960, 843 133; CA, 55, 2027i, (Carbenoxolone)
  • Witz, P. et al., Bull. Soc. Chim. Fr., 1963, 1101, (cd)
  • Budzikiewicz, H. et al., J.A.C.S., 1963, 85, 3688, (ms)
  • Murav'ev, I.A. et al., CA, 1966, 69, 44029v, (rev)
  • Canonica, L. et al., Gazz. Chim. Ital., 1967, 97, 1347; 1968, 98, 602, (Glycyrrhetol)
  • Robson, J.M. et al., Carbenoxolone Sodium, Orig. Pap. Discuss. Group Meet., Butterworth, London, 1969, (rev)
  • Wahlberg, I. et al., Acta Chem. Scand., 1971, 25, 3192, (ms)
  • Sandiya, R. et al., J. Het. Chem., 1984, 21, 845, (isol)
  • Tolstikov, G.A. et al., Khim. Prir. Soedin., 1985, 21, 645; Chem. Nat. Compd. (Engl. Transl.), 1985, 21, 605, (cmr)
  • Sakano, K. et al., Agric. Biol. Chem., 1986, 50, 763, (deriv)
  • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7889; 8042, (synonyms)
  • Kanaoka, M. et al., Chem. Pharm. Bull., 1988, 36, 3264, (synth)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 758; 873
  • Saito, S. et al., Chem. Pharm. Bull., 1994, 42, 1016, (synth)
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, GIE000; BGD000; GIEO5O; CBO500
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专利

专利

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