glycyrrhizic acid

glycyrrhetinic acid glycoside

CAS: 1405-86-3 C42 H62 O16 MW: 822.94334000 spicy sweet

Identification

Nameglycyrrhizic 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 Number1405-86-3
EINECS215-785-7
FDA UNII6FO62043WK
Molecular FormulaC42 H62 O16
Molecular Weight822.94334000
Nikkaji NumberJ1.238F
Beilstein0077922
CoE Number2221

Regulatory

FDA/DG SANTE Petitions, Reviews, Notices184.1408
DG SANTE Food Flavourings16.012 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

CosIngcosmetic data
Cosmetic Useshumectants

Organoleptic Properties

Odor Strength low
Odor Description at 100.00 %.
Taste Description sweet

Safety Information

Preferred SDSView
Oral/Parenteral Toxicityoral-human TDLo 5571 ug/kg/3D-
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorycosmetic and flavor agents
Recommendation for glycyrrhizic acid usage levels up tonot 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 Concern90 (μg/person/day)
Structure ClassIII
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

humectants FL licorice skin conditioning

Natural Occurrence

licorice root

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.