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1405-86-3

Basic Information
CAS No.: 1405-86-3
Name: Glycyrrhizic acid
Article Data: 9
Cas Database
Molecular Structure:
Molecular Structure of 1405-86-3 (Glycyrrhizic acid)
Formula: C42H62O16
Molecular Weight: 822.945
Synonyms: 6-[(11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl)oxy]-5-(6-carboxy-3,4,5-trihydroxy-oxan-2-yl)oxy-3,4-dihydroxy-oxane-2-carboxylic acid;See R-D-Glucopyranosiduronic acid,(3a,20a)-20-carboxy-11-oxo-30- norolean-12-en-3-yl 2-O-a-D-glucopyranuronosyl-;Glycyrrhizinic acid;Glycyrrhizinate;Rizinsan K2 A2 (free acid);Glycyrrizin;Glycyrrhizin (JAN);Glycrrhizin;Glycyron (TN);Glycyrrhetinic acid glycoside;Liquorice;
EINECS: 215-785-7
Density: 1.43 g/cm3
Melting Point: 220ºC decomposes
Boiling Point: 971.4 °C at 760 mmHg
Flash Point: 288.1 °C
Solubility: N/A
Appearance: White powder
Hazard Symbols: N/A
Risk Codes: N/A
Safety: 22-24/25
Transport Information: N/A
PSA: 267.04000
LogP: 2.24560
Synthetic route

diammonium glycyrrhizinate

A

1405-86-3

glycyrrhizin

B

18α-glycyrrhizic acid

Conditions
ConditionsYield
With sulfuric acid In methanol at 0℃; pH=3; Overall yield = 98 g;A n/a
B n/a

C45H68O15

1405-86-3

glycyrrhizin

Conditions
ConditionsYield
With sodium hydroxide for 2h; Reflux;8.5 g
30430-55-8

trimethyl glycyrrhizate

1405-86-3

glycyrrhizin

Conditions
ConditionsYield
With potassium hydroxide In ethanol; water for 2h; Heating; Yield given;
149553-79-7

C42H62O12

1405-86-3

glycyrrhizin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 31.3 percent / AgOTf, 1,1,3,3-tetramethylurea, Drierite / CH2Cl2 / 4 h / Ambient temperature
2: NaOMe / methanol / Ambient temperature
3: KOH / ethanol; H2O / 2 h / Heating
View Scheme

C44H61Cl3O13

1405-86-3

glycyrrhizin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 66.7 percent / NH3-sat. Et2O / 0.17 h / 0 °C
2: 31.3 percent / AgOTf, 1,1,3,3-tetramethylurea, Drierite / CH2Cl2 / 4 h / Ambient temperature
3: NaOMe / methanol / Ambient temperature
4: KOH / ethanol; H2O / 2 h / Heating
View Scheme
60192-37-2

C55H78O21

1405-86-3

glycyrrhizin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaOMe / methanol / Ambient temperature
2: KOH / ethanol; H2O / 2 h / Heating
View Scheme
1405-86-3

glycyrrhizin

AGR-GLY

Conditions
ConditionsYield
In water at 20℃; for 24h;95%
1405-86-3

glycyrrhizin

strontium glycyrrhizinate

Conditions
ConditionsYield
With strontium chloride In ethanol; water at 50℃; for 8h;93.7%
1405-86-3

glycyrrhizin

7585-39-9

β‐cyclodextrin

C42H62O16*C42H70O35

Conditions
ConditionsYield
In ethanol; water for 0.333333h; Sonication;93.5%
54-05-7

Chloroquine

1405-86-3

glycyrrhizin

chloroquine glycyrrhizinate

Conditions
ConditionsYield
In methanol at 55℃; for 8h; Inert atmosphere;91.5%
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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Glycyrrhizinic acid, with the CAS registry number 1405-86-3, is also known as 3-O-(2-O-beta-D-Glucopyranuronosyl-alpha-D-glucopyranuronosyl)-18beta-glycyrrhetinic acid. It belongs to the product categories of Tri-Terpenoids; Biochemistry; Disaccharides; Glycosides; Sugars; The group of Liquorice. Its EINECS registry number is 215-785-7. This chemical's molecular formula is C42H62O16 and molecular weight is 822.94. Its IUPAC name is called (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4alphaR,6alphaR,6betaS,8alphaS,11S,12alphaR,14alphaR,14betaS)-11-carboxy-4,4,6alpha,6blpha,8alpha,11,14beta-heptamethyl-14-oxo-2,3,4alpha,5,6,7,8,9,10,12,12alpha,14alpha-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid. This chemical's classification codes are Anti-Inflammatory Agents; Drug / Therapeutic Agent; Human Data; Mutation data. When you are using this chemical, please be cautious about it. You should not breathe its dust. In addition, you must avoid contacting it with skin and eyes.

Physical properties of Glycyrrhizinic acid: (1)ACD/LogP: 4.64; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): -0.7; (4)ACD/LogD (pH 7.4): -1.1; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 16; (10)#H bond donors: 8; (11)#Freely Rotating Bonds: 12; (12)Index of Refraction: 1.62; (13)Molar Refractivity: 201.36 cm3; (14)Molar Volume: 572.6 cm3; (15)Surface Tension: 73.6 dyne/cm; (16)Density: 1.43 g/cm3; (17)Flash Point: 288.1 °C; (18)Enthalpy of Vaporization: 160.44 kJ/mol; (19)Boiling Point: 971.4 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by supercritical CO2 extraction. The reaction time is 5 hours with reaction temperature of 40 °C.

Uses of Glycyrrhizinic acid: This chemical can be used as sweeteners, flavoring agents, flavor enhancers. Besides, It can be used as a drug for anti-inflammatory response. This chemical is used as a sweetener widely used in various types of food.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)[C@H]7O[C@@H](O[C@@H]6[C@@H](O)[C@H](O)[C@H](O[C@@H]6O[C@@H]2C(C)(C)[C@@H]3CC[C@@]1(C)[C@]5(C(=C/C(=O)[C@@H]1[C@@]3(C)CC2)\[C@@H]4C[C@](C(=O)O)(C)CC[C@]4(C)CC5)C)C(=O)O)[C@H](O)[C@@H](O)[C@@H]7O
(2)InChI: InChI=1/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1
(3)InChIKey: LPLVUJXQOOQHMX-QWBHMCJMBD

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
human TDLo oral 5571ug/kg/3D- (5.571mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION Toxicologist. Vol. 54, Pg. 109, 2000.
human TDLo oral 280mg/kg/4W (280mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) British Medical Journal. Vol. 1, Pg. 488, 1977.
man TDLo oral 662mg/kg/1Y-I (662mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: MUSCLE WEAKNESS
Internal Medicine. Vol. 31, Pg. 708, 1992.
mouse LD50 intravenous 589mg/kg (589mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 28, Pg. 215, 1993.
mouse LD50 oral 4320mg/kg (4320mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Zhongguo Yaoxue Zazhi. Chinese Pharmacuetical Journal. Vol. 28, Pg. 215, 1993.
mouse LDLo intraperitoneal 1gm/kg (1000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2041, 1977.
rat LD intravenous > 300mg/kg (300mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2041, 1977.
rat LDLo intraperitoneal 2gm/kg (2000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2041, 1977.
rat LDLo oral 3gm/kg (3000mg/kg)   Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 5, Pg. 2041, 1977.

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