glycyrrhizic acid
glycyrrhetinic acid glycoside
Identification
| Name | glycyrrhizic acid |
| IUPAC | (2S,3S,4S,5R,6R)-6-[(2S,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14 |
| CAS Number | 1405-86-3 |
| EINECS | 215-785-7 |
| FDA UNII | 6FO62043WK |
| Molecular Formula | C42 H62 O16 |
| Molecular Weight | 822.94334000 |
| Nikkaji Number | J1.238F |
| Beilstein | 0077922 |
| CoE Number | 2221 |
Regulatory
| FDA/DG SANTE Petitions, Reviews, Notices | 184.1408 |
| DG SANTE Food Flavourings | 16.012 glycyrrhizic acid |
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 200.00 to 214.00 °C. @ 760.00 mm Hg |
| Boiling Point | 970.00 to 972.00 °C. @ 760.00 mm Hg |
| Flash Point | 550.00 °F. TCC ( 287.78 °C. ) |
| logP (o/w) | 2.800 |
| Soluble in | alcohol |
| Insoluble in | water |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | humectants |
Organoleptic Properties
| Odor Strength | low |
| Odor Description | at 100.00 %. |
| Taste Description | sweet |
Safety Information
| Preferred SDS | View |
| Oral/Parenteral Toxicity | oral-human TDLo 5571 ug/kg/3D- |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | cosmetic and flavor agents |
| Recommendation for glycyrrhizic acid usage levels up to | not for fragrance use. |
| Maximised Survey-derived Daily Intakes (MSDI-EU) | 240.00 (μg/capita/day) |
| Modified Theoretical Added Maximum Daily Intake (mTAMDI) | 210000 (μg/person/day) |
| Threshold of Concern | 90 (μg/person/day) |
| Structure Class | III |
| Dairy products, excluding products of category 02.0 (01.0) | 375.00000 |
| Fats and oils, and fat emulsions (type water-in-oil) (02.0) | - |
| Edible ices, including sherbet and sorbet (03.0) | 375.00000 |
| Processed fruit (04.1) | - |
| Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2) | - |
| Confectionery (05.0) | 5000.00000 |
| Chewing gum (05.3) | - |
| Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0) | - |
| Bakery wares (07.0) | 200.00000 |
| Meat and meat products, including poultry and game (08.0) | 25.00000 |
| Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0) | 20.00000 |
| Eggs and egg products (10.0) | - |
| Sweeteners, including honey (11.0) | - |
| Salts, spices, soups, sauces, salads, protein products, etc. (12.0) | - |
| Foodstuffs intended for particular nutritional uses (13.0) | - |
| Non-alcoholic ("soft") beverages, excl. dairy products (14.1) | 50.00000 |
| Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2) | 550.00000 |
| Ready-to-eat savouries (15.0) | - |
| Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0) | 10.00000 |
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Potential Uses
Natural Occurrence
Synonyms
(3b,20b)-20-
carboxy-11-oxo-30-norolean-12-en-3-yl 2-O-b-D-glucopyranuronosyl-a-D-glucopyranosiduronic acid
20b-
carboxy-11-oxo-30-norolean-12-en-3b-yl-2-O-b-D-glucopyranuronosyl-a-D-glucopyranosiduronic acid
glycyram
glycyron
glycyrrhetinic acid glycoside
glycyrrhetinic acid, 18 alpha
glycyrrhetinic acid, 18 beta
18-beta-
glycyrrhizic acid
glycyrrhizin
glycyrrizin
potenlini
PubMed:
Liquorice, a unique "guide drug" of traditional Chinese medicine: a review of its role in drug interactions.
PubMed:
Exploring the possible metabolism mediated interaction of Glycyrrhiza glabra extract with CYP3A4 and CYP2D6.
PubMed:
Toxicologic evaluation of licorice extract as a cigarette ingredient.
PubMed:
Mutual interactions among ingredients of betel quid in inducing genotoxicity on Chinese hamster ovary cells.
PubMed:
A Review on the Role of Nutraceuticals as Simple as Se(2+) to Complex Organic Molecules Such as Glycyrrhizin That Prevent as Well as Cure Diseases.
PubMed:
Glycyrrhizic acid attenuated glycative stress in kidney of diabetic mice through enhancing glyoxalase pathway.
PubMed:
Antidepressant-like effects of Xiaochaihutang in a rat model of chronic unpredictable mild stress.
PubMed:
Formulating blackberry leaf mixtures for preparation of infusions with plant derived sources of sweeteners.
PubMed:
Ameliorative effect of Pracparatum mungo extract on high cholesterol diets in hamsters.
PubMed:
Rikkunshito ameliorates bleomycin-induced acute lung injury in a ghrelin-independent manner.
PubMed:
[Simultaneous determination of twelve sweeteners and nine preservatives in foods by solid-phase extraction and LC-MS/MS].
PubMed:
[About flavouring substances and flavouring preparations regulation in the field of manufacturing of flavourings and foodstuffs].
PubMed:
CDK2 and mTOR are direct molecular targets of isoangustone A in the suppression of human prostate cancer cell growth.
PubMed:
Water extract of licorice had anti-viral activity against human respiratory syncytial virus in human respiratory tract cell lines.
PubMed:
Subacute toxicity and stability of Soshiho-tang, a traditional herbal formula, in Sprague-Dawley rats.
PubMed:
Development of sample preparation method for isoliquiritigenin, liquiritin, and glycyrrhizic acid analysis in licorice by ionic liquids-ultrasound based extraction and high-performance liquid chromatography detection.
PubMed:
Anti-inflammatory effect of Sosihotang via inhibition of nuclear factor-kB and mitogen-activated protein kinases signaling pathways in lipopolysaccharide-stimulated RAW 264.7 macrophage cells.
PubMed:
Glycyrrhizic acid and 18beta-glycyrrhetinic acid recover glucocorticoid resistance via PI3K-induced AP1, CRE and NFAT activation.
PubMed:
Licorice abuse: time to send a warning message.
PubMed:
Liquorice reduced cyclosporine bioavailability by activating P-glycoprotein and CYP 3A.
PubMed:
Gamma-cyclodextrin production using cyclodextrin glycosyltransferase from Bacillus clarkii 7364.
PubMed:
Influence of fungal elicitation on glycyrrhizin production in transformed cell cultures of Abrus precatorius Linn.
PubMed:
Glycyrrhizic acid and 18beta-glycyrrhetinic acid modulate lipopolysaccharide-induced inflammatory response by suppression of NF-κB through PI3K p110δ and p110γ inhibitions.
PubMed:
Hexane/ethanol extract of Glycyrrhiza uralensis and its active compound isoangustone A induce G1 cycle arrest in DU145 human prostate and 4T1 murine mammary cancer cells.
PubMed:
Genotoxicity assessment of Pyungwi-san (PWS), a traditional herbal prescription.
PubMed:
Is glycyrrhizin sensitivity increased in anorexia nervosa and should licorice be avoided? Case report and review of the literature.
PubMed:
Glycyrrhizic acid and 18beta-glycyrrhetinic acid inhibit inflammation via PI3K/Akt/GSK3beta signaling and glucocorticoid receptor activation.
PubMed:
Hexane-ethanol extract of Glycyrrhiza uralensis containing licoricidin inhibits the metastatic capacity of DU145 human prostate cancer cells.
PubMed:
Quantification of glycyrrhizin in Glycyrrhiza glabra extract by validated HPTLC densitometry.
PubMed:
Inhibition of human renin activity by saponins.
PubMed:
EST analysis reveals putative genes involved in glycyrrhizin biosynthesis.
PubMed:
Roasted licorice extracts dampen high glucose-induced mesangial hyperplasia and matrix deposition through blocking Akt activation and TGF-beta signaling.
PubMed:
Isoangustone A present in hexane/ethanol extract of Glycyrrhiza uralensis induces apoptosis in DU145 human prostate cancer cells via the activation of DR4 and intrinsic apoptosis pathway.
PubMed:
Dietary exposure to flavouring substances: from screening methods to detailed assessments using food consumption data collected with EPIC-Soft software.
PubMed:
Determination of glycyrrhetic acid after consumption of liquorice and application to a fatality.
PubMed:
Liquorice alert.
PubMed:
[Culture of transgenic Glycyrrhiza uralensis hairy root with licorice squalene synthase (SQS) gene].
PubMed:
Rapid in vivo screening system for anti-oxidant activity using bacterial redox sensor strains.
PubMed:
Glycyrrhizin and licorice significantly affect the pharmacokinetics of methotrexate in rats.
PubMed:
Licorice flavonoids inhibit eotaxin-1 secretion by human fetal lung fibroblasts in vitro.
PubMed:
Neuroprotective effects of glycyrrhizic acid and 18beta-glycyrrhetinic acid in PC12 cells via modulation of the PI3K/Akt pathway.
PubMed:
Glycyrrhizic acid modulates t-BHP induced apoptosis in primary rat hepatocytes.
PubMed:
Effect of the extracts from Glycyrrhiza uralensis Fisch on the growth characteristics of human cell lines: Anti-tumor and immune activation activities.
PubMed:
Bimodal effect of glycyrrhizin on macrophage nitric oxide and prostaglandin E2 production.
PubMed:
Hexane/ethanol extract of Glycyrrhiza uralensis licorice suppresses doxorubicin-induced apoptosis in H9c2 rat cardiac myoblasts.
PubMed:
Biotransformation of ginsenoside Rb1, crocin, amygdalin, geniposide, puerarin, ginsenoside Re, hesperidin, poncirin, glycyrrhizin, and baicalin by human fecal microflora and its relation to cytotoxicity against tumor cells.
PubMed:
[Hypertension due to liquorice and liquorice tea consumption].
PubMed:
[Properties of commercial licorice extracts used as a food additive].
PubMed:
Determination of glycyrrhizin in liqueurs by on-line coupled capillary isotachophoresis with capillary zone electrophoresis.
PubMed:
Activation of rapid signaling pathways and the subsequent transcriptional regulation for the proliferation of breast cancer MCF-7 cells by the treatment with an extract of Glycyrrhiza glabra root.
PubMed:
Blockade of cytokine-induced endothelial cell adhesion molecule expression by licorice isoliquiritigenin through NF-kappaB signal disruption.
PubMed:
Simultaneous quantification of flavonoids and triterpenoids in licorice using HPLC.
PubMed:
Glycyrrhizin.
PubMed:
Risk and safety assessment on the consumption of Licorice root (Glycyrrhiza sp.), its extract and powder as a food ingredient, with emphasis on the pharmacology and toxicology of glycyrrhizin.
PubMed:
Simultaneous HPLC analysis, with isocratic elution, of glycyrrhizin and glycyrrhetic acid in liquorice roots and confectionery products.
PubMed:
Rapid detection of glycyrrhizin by immunochromatographic assay.
PubMed:
Evaluation of certain food additives.
PubMed:
[Analysis of nine kinds of sweeteners in foods by LC/MS].
PubMed:
Ultrasound-assisted extraction methodology as a tool to improve the antioxidant properties of herbal drug Xiao-chia-hu-tang.
PubMed:
Toxicologic evaluation of licorice extract as a cigarette ingredient.
PubMed:
[Simultaneous determination of stevioside, rebaudioside A and glycyrrhizic acid in foods by HPLC].
PubMed:
Effects of Sho-saiko-to extract and its components, Baicalin, baicalein, glycyrrhizin and glycyrrhetic acid, on pharmacokinetic behavior of salicylamide in carbon tetrachloride intoxicated rats.
PubMed:
Cytoprotective effects of Glycyrrhizae radix extract and its active component liquiritigenin against cadmium-induced toxicity (effects on bad translocation and cytochrome c-mediated PARP cleavage).
PubMed:
Anti-allergic activity of 18beta-glycyrrhetinic acid-3-O-beta-D-glucuronide.
PubMed:
Simultaneous identification of soyasaponins and isoflavones and quantification of soyasaponin Bb in soy products, using liquid chromatography/electrospray ionization-mass spectrometry.
PubMed:
Several culinary and medicinal herbs are important sources of dietary antioxidants.
PubMed:
Source of arsenic in licorice confectionery products.
PubMed:
[Prospect of the development of new bactericidal drugs against Helicobacter pylori for eradication therapy].
PubMed:
Efficient method for determining the glycyrrhizin content of fresh and dried roots, and root extracts, of Glycyrrhiza species.
PubMed:
Licorice and cancer.
PubMed:
Sweetener preference of C57BL/6ByJ and 129P3/J mice.
PubMed:
The pharmacokinetics of glycyrrhizic acid evaluated by physiologically based pharmacokinetic modeling.
PubMed:
Antidiabetic effect of glycyrrhizin in genetically diabetic KK-Ay mice.
PubMed:
Isolation and identification of main constituents in an enzymatically hydrolysed licorice extract sweetener.
PubMed:
Constituents and their sweetness of food additive enzymatically modified licorice extract.
PubMed:
Development of anorexia in concanavalin A-induced hepatitis in mice.
PubMed:
A population physiologically based pharmacokinetic/pharmacodynamic model for the inhibition of 11-beta-hydroxysteroid dehydrogenase activity by glycyrrhetic acid.
PubMed:
Inhibition of N-acetyltransferase activity and DNA-2-aminofluorene adducts by glycyrrhizic acid in human colon tumour cells.
PubMed:
Physiologically based pharmacokinetic modeling of glycyrrhizic acid, a compound subject to presystemic metabolism and enterohepatic cycling.
PubMed:
Effects of Sho-saiko-to extract on liver fibrosis in relation to the changes in hydroxyproline and retinoid levels of the liver in rats.
PubMed:
Cytotoxic and non-genotoxic effects of arecoline on human buccal fibroblasts in vitro.
PubMed:
Localization of enzymes involved in metabolism of glycyrrhizin in contents of rat gastrointestinal tract.
PubMed:
Glycyrrhizic acid in liquorice--evaluation of health hazard.
PubMed:
Inhibition of mutagenicity in Salmonella typhimurium and skin tumor initiating and tumor promoting activities in SENCAR mice by glycyrrhetinic acid: comparison of 18 alpha- and 18 beta-stereoisomers.
PubMed:
The determination of glycyrrhizin in selected UK liquorice products.
PubMed:
Effects of some purified saponins on transmural potential difference in mammalian small intestine.
PubMed:
Teratogenicity study of ammonium glycyrrhizinate in the Sprague-Dawley rat.
PubMed:
[Estimation of daily intake of glycyrrhizic acid according to the market basket studies in Japan (I)].
PubMed:
[Glycyrrhizin levels in various food stuffs].
PubMed:
Tests for mutagenic effects of ammoniated glycyrrhizin, butylated hydroxytoluene, and gum Arabic in rodent germ cells.
PubMed:
Tumorigenicity study of disodium glycyrrhizinate administered orally to mice.