18alpha-Glycyrrhetinic acid supplier

Name
18alpha-Glycyrrhetinic acid
EINECS 215-907-9
CAS No. 1449-05-4
Article Data16
CAS DataBase
Density 1.143 g/cm³
Solubility
Melting Point 331-333°C
Formula C₃₀H₄₆O₄
Boiling Point 588.337 °C at 760 mmHg
Molecular Weight 470.693
Flash Point 323.651 °C
Transport Information
Appearance
Safety ection
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms 18a-Olean-12-en-30-oic acid, 3b-hydroxy-11-oxo- (6CI,7CI,8CI);18-Isoglycyrrhetinic acid;18a-Glycyrrhetic acid;18a-Glycyrrhetinic acid;NSC 35350;STX 353;b-Glycyrrhetinic acid;
PSA 74.60000
LogP 6.41260

Synthetic route

: 650140-36-6
methyl 3-benzoyl-18α-glycyrrhetinate

: 1449-05-4
18-α-glycyrrhetinic acid

Conditions

Conditions	Yield
With sodium hydroxide In water; ethylene glycol; isopropyl alcohol for 2h; Heating;	84%

: 18α-glycyrrhizic acid

: 1449-05-4
18-α-glycyrrhetinic acid

Conditions

Conditions	Yield
With hydrogenchloride In water; acetic acid at 100℃; for 1h;	72%

: 471-53-4
enoxolone

: 1449-05-4
18-α-glycyrrhetinic acid

Conditions

Conditions	Yield
With potassium tert-butylate for 8h; Reagent/catalyst; Reflux;	68.5%
With potassium hydroxide In diethylene glycol for 2h; Reflux;	46%
With potassium hydroxide In diethylene glycol at 220℃; for 2h;	45%
With potassium hydroxide In diethylene glycol at 100 - 220℃;	43.7%
With hydrogenchloride; acetic acid

: methyl 18α,b-glycyrrhetinate

: 1449-05-4
18-α-glycyrrhetinic acid

Conditions

Conditions	Yield
With sodium hydroxide In water; ethylene glycol; isopropyl alcohol for 2h; Heating;	20%
Multi-step reaction with 2 steps 1: pyridine / 14 h / 20 °C 2: 84 percent / sodium hydroxide / H2O; propan-2-ol; ethane-1,2-diol / 2 h / Heating View Scheme

glycyrrhetinoic acid methyl ester: glycyrrhetinoic acid methyl ester

: 1449-05-4
18-α-glycyrrhetinic acid

Conditions

Conditions	Yield
With potassium hydroxide

: 18α-glycyrrhizic acid

A: 1449-05-4
18-α-glycyrrhetinic acid

B: glycyrrhetic acid 3-O-mono-β-D-glucuronide

Conditions

Conditions	Yield
With β-glucuronidase Kinetics; Reagent/catalyst; Enzymatic reaction;

: glycyrrhetic acid 3-O-mono-β-D-glucuronide

: 1449-05-4
18-α-glycyrrhetinic acid

Conditions

Conditions	Yield
With β-glucuronidase for 10h; Enzymatic reaction;

: 186581-53-3, 908094-01-9
diazomethane

: 1449-05-4
18-α-glycyrrhetinic acid

: 5092-01-3
(3β,18α)-methyl 3-hydroxy-11-oxoolean-12-30-oate

Conditions

Conditions	Yield
In diethyl ether	100%
In diethyl ether; dichloromethane	76.3%

: 1449-05-4
18-α-glycyrrhetinic acid

: 74-88-4
methyl iodide

: 5092-01-3
(3β,18α)-methyl 3-hydroxy-11-oxoolean-12-30-oate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 2h;	86%

: 1449-05-4
18-α-glycyrrhetinic acid

: 908093-98-1
diazodiphenylmethane

: 441759-67-7
(3β,18α,20β)-3-hydroxy-11-oxoolean-12-en-29-oic acid diphenylmethyl ester

Conditions

Conditions	Yield
In methanol; diethyl ether at 45℃;	84%

: 1449-05-4
18-α-glycyrrhetinic acid

: 6184-16-3
3,11-dioxo-18α-olean-12-en-30-oic acid

Conditions

Conditions	Yield
With chromium trioxide-pyridine complex In dichloromethane at 20℃; for 1h;	80%

: 1449-05-4
18-α-glycyrrhetinic acid

: 251105-80-3
N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride

: (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-10-hydroxy-N-((2S,3R)-3-hydroxy-4-(N-isobutyl-4-nitrophenylsulfonamido)-1-phenylbutan-2-yl)-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-carboxamide

Conditions

Conditions	Yield
Stage #1: 18-α-glycyrrhetinic acid; N-(3S-amino-2R-hydroxy-4-phenylbutyl)-N-isobutyl-4-nitro-benzenesulfonamide hydrochloride With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere; Stage #2: With dmap at 20℃; for 11h; Inert atmosphere;	69%

: 1449-05-4
18-α-glycyrrhetinic acid

: 159005-71-7
N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide

: (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-10-hydroxy-N-((2S,3R)-3-hydroxy-4-(N-isobutyl-4-methoxyphenylsulfonamido)-1-phenylbutan-2-yl)-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-carboxamide

Conditions

Conditions	Yield
Stage #1: 18-α-glycyrrhetinic acid; N-((2R,3S)-3-amino-2-hydroxy-4-phenylbutyl)-N-isobutyl-4-methoxybenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere; Stage #2: With dmap at 20℃; for 11h; Inert atmosphere;	65%

: 1449-05-4
18-α-glycyrrhetinic acid

: 169280-56-2
4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide

: (2S,4aS,6aS,6bR,8aR,10S,12aS,12bR,14bS)-N-((2S,3R)-4-(4-amino-N-isobutylphenylsulfonamido)-3-hydroxy-1-phenylbutan-2-yl)-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-carboxamide

Conditions

Conditions	Yield
Stage #1: 18-α-glycyrrhetinic acid; 4-amino-N-(2R,3S)(3-amino-2-hydroxy-4-phenylbutyl)-N-isobutylbenzenesulfonamide With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 1.16667h; Inert atmosphere; Stage #2: With dmap at 20℃; for 11h; Inert atmosphere;	65%

: 1449-05-4
18-α-glycyrrhetinic acid

: 5092-01-3
(3β,18α)-methyl 3-hydroxy-11-oxoolean-12-30-oate

Conditions

Conditions	Yield
With diazomethane; methanol; diethyl ether

: 1449-05-4
18-α-glycyrrhetinic acid

: 108-24-7
acetic anhydride

: 18305-96-9
3β-acetoxy-11-oxo-18α-oleanen-(12)-oic acid-(30)

Conditions

Conditions	Yield
With pyridine

: 186581-53-3, 908094-01-9
diazomethane

: 108-30-5
succinic acid anhydride

: 1449-05-4
18-α-glycyrrhetinic acid

: 17175-23-4
Methyl 3-O-(β-carboxypropionyl)-18α-glycyrrhetat

Conditions

Conditions	Yield
(i) MeOH, Et2O, (ii) /BRN= 108441/, Py; Multistep reaction;

...Expand

: 1449-05-4
18-α-glycyrrhetinic acid

: 60209-40-7
11-oxo-18α-olean-12-ene-3β,30-diol

Conditions

Conditions	Yield
With manganese(IV) oxide; lithium aluminium tetrahydride 1.) THF, 60 deg C, 1 h, 2.) CHCl3, THF, 25 h; Yield given. Multistep reaction;

: 1449-05-4
18-α-glycyrrhetinic acid

: 6588-91-6
(18α)-methyl 3,11-dioxoolean-12-en-30-oate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / CrO3-Py / CH2Cl2 / 1 h / 20 °C 2: 100 percent / diethyl ether View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 25 °C View Scheme

: 1449-05-4
18-α-glycyrrhetinic acid

: methyl β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-3-O-18α-glycyrrhetinate

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 31.1 percent / Ag2O; I2 / CHCl3 / 48 h / 20 °C 2: 405 mg / sodium methylate / CHCl3 / 1.5 h / -20 °C 3: 85 mg / H2 / 10 percent Pd/C / methanol / 20 °C / 2587.71 Torr 4: 65.5 percent / diethyl ether; methanol / 1 h View Scheme

: 1449-05-4
18-α-glycyrrhetinic acid

: 22596-24-3
β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-3-O-18α-glycyrrhetic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 31.1 percent / Ag2O; I2 / CHCl3 / 48 h / 20 °C 2: 405 mg / sodium methylate / CHCl3 / 1.5 h / -20 °C 3: 85 mg / H2 / 10 percent Pd/C / methanol / 20 °C / 2587.71 Torr View Scheme

: 1449-05-4
18-α-glycyrrhetinic acid

: C55H76O14

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 31.1 percent / Ag2O; I2 / CHCl3 / 48 h / 20 °C 2: 405 mg / sodium methylate / CHCl3 / 1.5 h / -20 °C View Scheme

: 1449-05-4
18-α-glycyrrhetinic acid

: 441759-70-2
diphenylmethyl 2',3',6',2'',3'',4'',6''-heptaacetyl-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-3-O-18α-glycyrrhetinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 31.1 percent / Ag2O; I2 / CHCl3 / 48 h / 20 °C View Scheme

: 1449-05-4
18-α-glycyrrhetinic acid

: 10301-82-3
(3β,18α)-methyl 3-acetoxy-11-oxoolean-12-en-30-oate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: diazomethane; diethyl ether View Scheme
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 25 °C 2: pyridine / dichloromethane / 2 h / 25 °C View Scheme

: 1449-05-4
18-α-glycyrrhetinic acid

A: (3α,18α)-methyl 3-amino-11-oxoolean-12-en-30-oate

B: (3β,18α)-methyl 3-amino-11-oxoolean-12-en-30-oate

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 25 °C 3: ammonium acetate; sodium cyanoborohydride / methanol / 24 h / 25 °C View Scheme

: 1449-05-4
18-α-glycyrrhetinic acid

A: (3β)-methyl 3-acetoxy-13-carboxy-19-hydroxy-11-oxo-C-norolean-18-en-30-oate-12,19-lactone

B: (3β,18β)-3-acetoxy-18-hydroxy-11-oxoolean-12-en-30-oic acid-30,18-lactone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 25 °C 2: pyridine / dichloromethane / 2 h / 25 °C 3: acetic acid; selenium(IV) oxide / 4 h / 145 °C / Microwave irradiation View Scheme

: 1449-05-4
18-α-glycyrrhetinic acid

: 3-ethoxycarbonyl-7-oxabicyclo[2.2.1]heptane-2-carbonyl chloride

: 3β-(2-formyl-7-oxabicyclo[2.2.1]heptane-3-carbethoxy)oxy-18α-glycyrrhetinic acid

Conditions

Conditions	Yield
With dmap In dichloromethane for 10h; Reflux;

: 15307-86-5
[2-(2,6-dichloroanilino)phenyl]acetic acid

: 1449-05-4
18-α-glycyrrhetinic acid

: DC

Conditions

Conditions	Yield
With pyridine; dmap In dichloromethane at 30℃;

: 1449-05-4
18-α-glycyrrhetinic acid

: 2616-64-0
UDP-glucuronic acid

: 18α-glycyrrhetinic acid 30-O-β-D-glucoside

Conditions

Conditions	Yield
With recombinant Glycyrrhiza uralensis glycosyltransferase UGT73F17; magnesium(II) In aq. phosphate buffer at 45℃; for 12h; pH=7.5; regiospecific reaction;

18alpha-Glycyrrhetinic acid Chemical Properties

Molecular Formula: C₃₀H₄₆O4
Molar mass: 470.68 g/mol
EINECS: 215-907-9
Density: 1.14 g/cm³
Flash Point: 323.7 °C
Index of Refraction: 1.562
Boiling Point: 588.3 °C at 760 mmHg
Vapour Pressure: 2.71E-16 mmHg at 25 °C
Melting point: 331-333 °C
Product categories of 18alpha-Glycyrrhetinic acid (CAS NO.1449-05-4): Tri-Terpenoids
Structure of 18alpha-Glycyrrhetinic acid (CAS NO.1449-05-4):

XLogP3-AA: 6.4
H-Bond Donor: 2
H-Bond Acceptor: 4
IUPAC Name: 10-Hydroxy-2,4a,6a,6b,9,9,12a-heptamethyl-13-oxo-3,4,5,6,6a,7,8,8a,10,11,12,14b-dodecahydro-1H-picene-2-carboxylic acid
Canonical SMILES: CC1(C2CCC3(C(C2(CCC1O)C)C(=O)C=C4C3(CCC5(C4CC(CC5)(C)C(=O)O)C)C)C)C
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)
InChIKey: MPDGHEJMBKOTSU-UHFFFAOYSA-N

18alpha-Glycyrrhetinic acid Toxicity Data With Reference

1.	orl-mus LD50:560 mg/kg	CPBTAL Chemical and Pharmaceutical Bulletin. 28 (1980),3449.
2.	ipr-mus LD50:455 mg/kg	CPBTAL Chemical and Pharmaceutical Bulletin. 28 (1980),3449.
3.	ivn-mus LD50:100 mg/kg	CSLNX* U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#02068 .

18alpha-Glycyrrhetinic acid Safety Profile

Poison by intravenous route. Moderately toxic by ingestion and intraperitoneal routes. When heated to decomposition it emits acrid smoke and irritating fumes.

Hazard Codes of 18alpha-Glycyrrhetinic acid (CAS NO.1449-05-4): Harmful Xn
Risk Statements:
R22:Harmful if swallowed.

18alpha-Glycyrrhetinic acid Specification

18alpha-Glycyrrhetinic acid ,its cas register number is 1449-05-4. It also can be called beta-Glycyrrhetinic acid ; 18-alpha-Olean-12-en-30-oic acid, 3-beta-hydroxy-11-oxo- and (3beta,18alpha,20beta)-3-Hydroxy-11-oxoolean-12-en-29-oic acid .

Product Name

18alpha-Glycyrrhetinic acid

Synthetic route

18alpha-Glycyrrhetinic acid Chemical Properties

18alpha-Glycyrrhetinic acid Toxicity Data With Reference

18alpha-Glycyrrhetinic acid Safety Profile

18alpha-Glycyrrhetinic acid Specification

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