Name: Glycyrrhizic acid
SKU: 1405-86-3

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Basic Information

Molecular Structure:
CAS No.:	1405-86-3
Name:	Glycyrrhizic acid
Article Data:	9

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
Appearance:	White powder
Safety:	22-24/25
PSA:	267.04000
LogP:	2.24560

Synthetic route

: diammonium glycyrrhizinate

A: 1405-86-3
glycyrrhizin

B: 18α-glycyrrhizic acid

Conditions

Conditions	Yield
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

Conditions	Yield
With sodium hydroxide for 2h; Reflux;	8.5 g

: 30430-55-8
trimethyl glycyrrhizate

: 1405-86-3
glycyrrhizin

Conditions

Conditions	Yield
With potassium hydroxide In ethanol; water for 2h; Heating; Yield given;

: 149553-79-7
C42H62O12

: 1405-86-3
glycyrrhizin

Conditions

Conditions	Yield
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

Conditions	Yield
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

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

: 7200-25-1
Arg

: 1405-86-3
glycyrrhizin

: AGR-GLY

Conditions

Conditions	Yield
In water at 20℃; for 24h;	95%

: 1405-86-3
glycyrrhizin

: strontium glycyrrhizinate

Conditions

Conditions	Yield
With strontium chloride In ethanol; water at 50℃; for 8h;	93.7%

: 1405-86-3
glycyrrhizin

: 7585-39-9
β‐cyclodextrin

: C42H62O16*C42H70O35

Conditions

Conditions	Yield
In ethanol; water for 0.333333h; Sonication;	93.5%

: 54-05-7
Chloroquine

: 1405-86-3
glycyrrhizin

: chloroquine glycyrrhizinate

Conditions

Conditions	Yield
In methanol at 55℃; for 8h; Inert atmosphere;	91.5%

Downstream Products

53-96-3

471-53-4

6556-12-3

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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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Consensus Reports

Specification