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P0376

Sigma-Aldrich

Phenolphthalein β-D-glucuronide sodium salt

β-glucuronidase substrate, chromogenic, ≥90% (TLC), powder

Synonym(s):

Phenolphthalein glucuronic acid, Phenolphthalein mono-β-glucosiduronic acid

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About This Item

Linear Formula:
C26H21O10Na
CAS Number:
6820-54-8
Molecular Weight:
516.43
EC Number:
229-896-3
MDL number:
MFCD00051200
UNSPSC Code:
12352204
PubChem Substance ID:
329820033
NACRES:
NA.28

product name

Phenolphthalein β-D-glucuronide sodium salt, β-glucuronidase substrate

Assay

≥90% (TLC)

form

powder

solubility

H2O: soluble 5 mg/mL

storage temp.

−20°C

SMILES string

[Na+].O[C@@H]1[C@@H](O)[C@@H](O[C@@H]([C@H]1O)C([O-])=O)Oc2ccc(cc2)C3(OC(=O)c4ccccc34)c5ccc(O)cc5

InChI

1S/C26H22O10.Na/c27-15-9-5-13(6-10-15)26(18-4-2-1-3-17(18)24(33)36-26)14-7-11-16(12-8-14)34-25-21(30)19(28)20(29)22(35-25)23(31)32;/h1-12,19-22,25,27-30H,(H,31,32);/q;+1/p-1/t19-,20-,21+,22-,25+,26?;/m0./s1

InChI key

GBLJULUMBNYFAK-PDFLYTMFSA-M

Biochem/physiol Actions

Phenolphthalein β-D-glucuronide sodium salt is a β glucuronidase substrate. It is biosynthesized from the urine of rabbits to which phenolphthalein has been administered.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Chromogenic substrates II. Phenolphthalein glucuronic acid as substrate for the assay of glucuronidase activity
Talalay P, et al.
The Journal of Biological Chemistry, 166(2), 757-772 (1946)
[9] Preparation and assay of substrates for $\beta$-glucuronidase
Fishman WH
Test (1957)
M Tugnait et al.
Journal of pharmaceutical and biomedical analysis, 9(10-12), 895-899 (1991-01-01)
Preliminary studies have been undertaken to evaluate the potential of immobilized phenylboronic acid (PBA) for the solid-phase extraction (SPE) of glucuronide metabolites from urine. These studies have demonstrated that immobilized PBA can be used to specifically extract phenolphthalein glucuronide (5
Miklós Csala et al.
Biochemical pharmacology, 68(7), 1353-1362 (2004-09-04)
The transport of glucuronides across the endoplasmic reticulum membrane is an important step in the overall process of biotransformation, although the mechanism remains unclear and the participating transporters are unidentified. Using a rapid filtration assay in combination with liquid chromatography-mass
W E Kurtin et al.
Analytical biochemistry, 147(2), 511-516 (1985-06-01)
A method for improving the assay of beta-glucuronidase in hepatic and gallbladder bile is described. The method uses ion-pair extraction with N,N,N-triheptyl-1-heptanaminium bromide to remove pigments and bile acids. Conjugated bilirubin, unconjugated bilirubin, and taurine and glycine conjugates of deoxycholic
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