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471-53-4 molecular structure
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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 ID: 72941
Molecular Formular: C30H46O4
Molecular Mass: 470.68384
Monoisotopic Mass: 470.33960995
SMILES and 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

Cite this record

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

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(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 Traditional name
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
Synonyms
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
甘草次酸
18β-甘草次酸
CAS Number
471-53-4
EC Number
207-444-6
MDL Number
MFCD00003706
Beilstein Number
2229654
PubChem SID
162037861
24873370
24895033
PubChem CID
10114
CHEBI ID
30853
ATC CODE
D03AX10
CHEMBL
230006
Chemspider ID
9710
Wikipedia Title
Glycyrrhetinic_acid

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Polar Surface Area 74.6 Å2 Rotatable Bonds
Lipinski's Rule of Five false  Acid pKa 4.4443316 
H Acceptors H Donor
LogD (pH = 5.5) 4.940498  LogD (pH = 7.4) 3.1778886 
Log P 6.031328  Molar Refractivity 134.2685 cm3
Polarizability 53.29785 Å3

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Melting Point
292-295 °C(lit.) expand Show data source
Optical Rotation
[α]20/D +165±3°, c = 1% in chloroform expand Show data source
[α]22/D +170.0°, c = 1 in chloroform expand Show data source
Storage Condition
-20°C expand Show data source
RTECS
RK0180000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22-36 expand Show data source
Safety Statements
22-24/25 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302-H319 expand Show data source
GHS Precautionary statements
P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Gene Information
human ... HSD11B1(3290), HSD11B2(3291)rat ... Hsd11b1(25116), Hsd11b2(25117) expand Show data source
Mechanism of Action
Calcium-mobilizer in P815 cells in-vitro expand Show data source
Reported to inhibit reactive oxygen species generation by human neutrophils in-vitro expand Show data source
Reported to trap hydroxyl radicals to suppress rat liver injury caused by ischemia-perfusion expand Show data source
Purity
≥97.0% (T) expand Show data source
97% expand Show data source
Grade
purum expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Biological Source
Aglycone from Glycyrrhiza glabra and some other plants expand Show data source
Application(s)
Antibacterial, antitussive agent expand Show data source
Antiinflammatory expand Show data source
Used in treatment of noninfective inflammatory disorders (skin, mouth, etc.) expand Show data source
Empirical Formula (Hill Notation)
C30H46O4 expand Show data source

DETAILS

DETAILS

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
Packaging
10, 25 g in poly bottle
Toronto Research Chemicals - G735000 external link
An anti-inflammatory (topical).

REFERENCES

REFERENCES

From Suppliers 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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PATENTS

PATENTS

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INTERNET

INTERNET

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