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50531

Sigma-Aldrich

Glycyrrhizic acid ammonium salt from glycyrrhiza root (licorice)

≥95.0% (NT)

Synonym(s):

3-O-(2-O-β-D-Glucopyranuronosyl-α-D-glucopyranuronosyl)-18β-glycyrrhetinic acid ammonium salt, Glycyrrhizin

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About This Item

Linear Formula:
C42H62O16 · NH3
CAS Number:
53956-04-0
Molecular Weight:
839.96
Beilstein:
3897076
EC Number:
258-887-7
MDL number:
MFCD00167400
UNSPSC Code:
12352106
PubChem Substance ID:
57651257
NACRES:
NA.76
Pricing and availability is not currently available.

Assay

≥95.0% (NT)

optical activity

[α]20/D +48±4°, c = 1% in ethanol: water (1:1)

sweetness

50 × sucrose

impurities

≤7% water

SMILES string

N.CC1(C)[C@H](CC[C@@]2(C)[C@H]1CC[C@]3(C)[C@@H]2C(=O)C=C4[C@@H]5C[C@](C)(CC[C@]5(C)CC[C@@]34C)C(O)=O)O[C@H]6O[C@@H]([C@@H](O)[C@H](O)[C@H]6O[C@@H]7O[C@@H]([C@@H](O)[C@H](O)[C@H]7O)C(O)=O)C(O)=O

InChI

1S/C42H62O16.H3N/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);1H3/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30+,31+,34-,35-,38+,39-,40-,41+,42+;/m0./s1

InChI key

ILRKKHJEINIICQ-OOFFSTKBSA-N

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Related Categories

Biochem/physiol Actions

Biologically active constituent in the sweet root of Glycyrrhiza species (licorice). Antiviral.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H319

Hazard Classifications

Eye Irrit. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM3023
BCCK4968
BCCJ0144
BCCC1931
BCBX4974

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Beilei Liu et al.
Oxidative medicine and cellular longevity, 2019, 1703709-1703709 (2020-01-14)
High mobility group box 1 (HMGB1) participates actively in oxidative stress damage and the latter relates closely to diabetic complications, including poor implant osseointegration. This article is aimed at investigating the effects of HMGB1 on dysfunction of bone marrow stromal
Guannan Li et al.
European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences, 109, 182-190 (2017-08-05)
The potential of licorice dietary supplements to interact with drug metabolism was evaluated by testing extracts of three botanically identified licorice species (Glycyrrhiza glabra L., Glycyrrhiza uralensis Fish. ex DC. and Glycyrrhiza inflata Batalin) and 14 isolated licorice compounds for
Oluwaseun O Ojo et al.
American journal of physiology. Lung cellular and molecular physiology, 309(11), L1354-L1366 (2015-10-04)
High mobility group box 1 (HMGB1) is a damage-associated molecular pattern (DAMP) protein that binds Toll-like receptors (e.g., TLR4) and the receptor for advanced glycated end products (RAGE). The direct effects of HMGB1 on airway structural cells are not fully
Guangyi Zhao et al.
PloS one, 14(9), e0222369-e0222369 (2019-09-29)
Mechanical overloading is a major cause of tendinopathy, but the underlying pathogenesis of tendinopathy is unclear. Here we report that high mobility group box1 (HMGB1) is released to the tendon extracellular matrix and initiates an inflammatory cascade in response to
Yu Okuma et al.
Neuropharmacology, 85, 18-26 (2014-05-27)
Glycyrrhizin (GL) is a major constituent of licorice root and has been suggested to inhibit the release of high mobility group box-1 (HMGB1), a protein considered representative of damage-associated molecular patterns. We found that GL bound HMGB1 but not RAGE
View All Related Papers

Questions

1–3 of 3 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. What is the solubility of product 50531 (Glycyrrhizic acid ammonium salt from glycyrrhiza root - licorice)?

    1 answer

    1. Solubility testing is not conducted. However, information from literature and web sources indicates the following:
      1.Slightly soluble in water
      2.Soluble in 1 M NH4OH (50 mg/ml)
      3.Soluble in Acetic Acid
      4.Soluble in Chloroform, Dichloromethane, Ethyl Acetate, DMSO
      5.Very slightly soluble in anhydrous ethanol
      6.It dissolves in dilute solutions of acids and of alkali hydroxides

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