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Merck

G10105

Sigma-Aldrich

18β-Glycyrrhetinic acid

97%

Sinónimos:

3β-Hydroxy-11-oxo-18β,20β-olean-12-en-29-oic acid, Enoxolone, Glycyrrhetin, Subglycyrrhelinic acid, Uralenic acid

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About This Item

Fórmula empírica (notación de Hill):
C30H46O4
Número de CAS:
Peso molecular:
470.68
Beilstein:
2229654
Número CE:
Número MDL:
Código UNSPSC:
12352115
ID de la sustancia en PubChem:
NACRES:
NA.22
En este momento no podemos mostrarle ni los precios ni la disponibilidad

Nivel de calidad

Ensayo

97%

actividad óptica

[α]22/D +170.0°, c = 1 in chloroform

mp

292-295 °C (lit.)

cadena SMILES

CC1(C)[C@@H](O)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

InChI

1S/C30H46O4/c1-25(2)21-8-11-30(7)23(28(21,5)10-9-22(25)32)20(31)16-18-19-17-27(4,24(33)34)13-12-26(19,3)14-15-29(18,30)6/h16,19,21-23,32H,8-15,17H2,1-7H3,(H,33,34)/t19-,21-,22-,23+,26+,27-,28-,29+,30+/m0/s1

Clave InChI

MPDGHEJMBKOTSU-YKLVYJNSSA-N

Información sobre el gen

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Descripción general

18β-Glycyrrhetinic acid is a pentacyclic triterpenoid found in the Glycyrrhiza glabra L.(liquorice) roots.[1] It is the key metabolite of glycyrrhizin[2] and glycyrrhizic acid.[3]

Aplicación

The product may be used as a starting material to prepare 18β-glycyrrhetinic acid derivatives, which show anti-inflammatory and antioxidant properties.[4]

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 2

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves


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Certificados de análisis (COA)

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Christian Stanetty et al.
Bioorganic & medicinal chemistry, 18(21), 7522-7541 (2010-09-21)
Glycyrrhetinic acid, the metabolite of the natural product glycyrrhizin, is a well known nonselective inhibitor of 11β-hydroxysteroid dehydrogenase (11β-HSD) type 1 and type 2. Whereas inhibition of 11β-HSD1 is currently under consideration for treatment of metabolic diseases, such as obesity
Synthesis, anti-inflammatory, and antioxidant activities of 18?-glycyrrhetinic acid derivatives as chemical mediators and xanthine oxidase inhibitors.
Maitraie D, et al.
Bioorganic & Medicinal Chemistry, 17(7), 2785-2792 (2009)
Gaëlle Le Bras et al.
Journal of medicinal chemistry, 50(24), 6189-6200 (2007-11-06)
Selective hsp90 inhibitors simultaneously destabilize and deplete key signaling proteins involved in cell proliferation and survival, angiogenesis, and metastasis. Investigation of novobiocin analogues lacking the noviose moiety as novel inhibitors of hsp90 was carried out. A novel series of 3-aminocoumarin
From Test Tube to Clinical Trial; Promising Herbs with NF-?B and COX-2 Activity.
Wilkinson F and Cundell DR
Current Immunology Reviews, 10(2), 82-98 (2014)
Igor Beseda et al.
Bioorganic & medicinal chemistry, 18(1), 433-454 (2009-11-17)
The effect of glycyrrhetinic acid (GA) and GA-derivatives towards 11beta-hydroxysteroid dehydrogenase (11beta-HSD) was investigated. Novel compounds with modifications at positions C-3, C-11 and C-29 of the GA skeleton were prepared. Single crystal X-ray diffraction data of selected substances are reported

Questions

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  1. 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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  2. 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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