(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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• 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

• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: false
• Acid pKa: 4.4443316
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.940498
• LogD (pH = 7.4): 3.1778886
• Log P: 6.031328
• Molar Refractivity: 134.2685 cm^3
• Polarizability: 53.29785 Å^3

PROPERTIES

Physical Property

• Melting Point: 292-295 °C(lit.)
• Optical Rotation: [α]20/D +165±3°, c = 1% in chloroform; [α]22/D +170.0°, c = 1 in chloroform

Safety Information

• Storage Condition: -20°C
• RTECS: RK0180000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36
• Safety Statements: 22-24/25
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Gene Information: human ... HSD11B1(3290), HSD11B2(3291)rat ... Hsd11b1(25116), Hsd11b2(25117)
• Mechanism of Action: Calcium-mobilizer in P815 cells in-vitro; Reported to inhibit reactive oxygen species generation by human neutrophils in-vitro; Reported to trap hydroxyl radicals to suppress rat liver injury caused by ischemia-perfusion

Product Information

• Purity: ≥97.0% (T); 97%
• Grade: purum
• Salt Data: Free Base
• Biological Source: Aglycone from Glycyrrhiza glabra and some other plants
• Application(s): Antibacterial, antitussive agent; Antiinflammatory; Used in treatment of noninfective inflammatory disorders (skin, mouth, etc.)
• Empirical Formula (Hill Notation): C30H46O4

DETAILS

Selleck Chemicals - S2296

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

Packaging
10, 25 g in poly bottle

Toronto Research Chemicals - G735000

An anti-inflammatory (topical).

REFERENCES

• 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