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1449-05-4

Basic Information
CAS No.: 1449-05-4
Name: 18alpha-Glycyrrhetinic acid
Article Data: 16
Molecular Structure:
Molecular Structure of 1449-05-4 (18alpha-Glycyrrhetinic acid)
Formula: C30H46O4
Molecular Weight: 470.693
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;
EINECS: 215-907-9
Density: 1.143 g/cm3
Melting Point: 331-333°C
Boiling Point: 588.337 °C at 760 mmHg
Flash Point: 323.651 °C
Hazard Symbols: HarmfulXn
Risk Codes: 22
Safety: ection
PSA: 74.60000
LogP: 6.41260
Synthetic route
650140-36-6

methyl 3-benzoyl-18α-glycyrrhetinate

1449-05-4

18-α-glycyrrhetinic acid

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

18α-glycyrrhizic acid

1449-05-4

18-α-glycyrrhetinic acid

Conditions
ConditionsYield
With hydrogenchloride In water; acetic acid at 100℃; for 1h;72%
471-53-4

enoxolone

1449-05-4

18-α-glycyrrhetinic acid

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With potassium hydroxide

18α-glycyrrhizic acid

A

1449-05-4

18-α-glycyrrhetinic acid

B

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

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

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

1449-05-4

18-α-glycyrrhetinic acid

Conditions
ConditionsYield
With β-glucuronidase for 10h; Enzymatic reaction;
1449-05-4

18-α-glycyrrhetinic acid

5092-01-3

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

Conditions
ConditionsYield
In diethyl ether100%
In diethyl ether; dichloromethane76.3%
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
ConditionsYield
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
ConditionsYield
In methanol; diethyl ether at 45℃;84%
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  • 1449-05-4          C30H46O4              18alpha-Glycyrrhetinic acid

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    1449-05-4 C30H46O4 18alpha-Glycyrrhetinic acid

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Chemistry

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

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 .

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): HarmfulXn
Risk Statements:
R22:Harmful if swallowed.

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 .