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77636

Sigma-Aldrich

Phenolphthalein β-D-glucuronide

≥98% (TLC)

Synonym(s):

Phenolphthalein β-D-glucosiduronic acid, Phenolphthalein glucuronic acid, Phenolphthalein mono-β-D-glucosiduronic acid

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About This Item

Empirical Formula (Hill Notation):
C26H22O10
CAS Number:
15265-26-6
Molecular Weight:
494.45
Beilstein:
68526
MDL number:
MFCD00135881
UNSPSC Code:
12352204
PubChem Substance ID:
329767834
NACRES:
NA.83

biological source

rabbit urine

Assay

≥98% (TLC)

form

powder

impurities

≤0.5% free phenolphthalein
≤6% water

solubility

H2O: 0.1 g/mL, clear, light yellow

storage temp.

−20°C

SMILES string

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/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)/t19-,20-,21+,22-,25+,26?/m0/s1

InChI key

FXJYOZKDDSONLX-XADSOVDISA-N

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Application

β-glucuronidase test: suitable as substrate, for liver and bacterial enzymes

Other Notes

Characterization of β-glucuronidase from Ampullaria

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
BCBZ4994

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T. Tsukada et al.
Comparative Biochemistry and Physiology, 86B, 565-565 (1987)
Inhibitory effect of bile acids on the activity of human beta-glucuronidase at its optimal pH.
K J Ho et al.
Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.), 167(3), 304-309 (1981-07-01)
Z K Sharaiha et al.
Digestive diseases and sciences, 28(9), 827-832 (1983-09-01)
Phenolphthalein is an odorless, tasteless compound, poorly soluble in water, but readily soluble in alcohol or ether. Although its laxative activity was discovered in 1902, the mechanism of action remains unclear. Phenolphthalein has been found to be an ineffective laxative
L K Griffeth et al.
Drug metabolism and disposition: the biological fate of chemicals, 13(4), 391-397 (1985-07-01)
A previously validated small mammal trauma model, hind-limb ischemia secondary to infrarenal aortic ligation in the rat, was utilized to investigate the effects of traumatic injury on hepatic glucuronidation activity. As was previously observed with hepatic oxidative drug metabolism, model
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
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