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Merck
CN

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

Key Documents

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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

Regulatory Information

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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)
B S Anand et al.
Alimentary pharmacology & therapeutics, 8(5), 559-562 (1994-10-01)
Phenolphthalein is widely used as a safe and effective laxative. After oral administration, phenolphthalein is absorbed in the small bowel and is conjugated in the liver to phenolphthalein glucuronide which passes into the colon where it is deconjugated and the
Tatsuyuki Marumo et al.
Journal of gastroenterology, 39(10), 981-987 (2004-11-19)
Hepatocytes in zone 1 of the hepatic lobule play a role in the uptake and biliary excretion of bile acids and organic anions under physiological conditions, and hepatocytes in zone 3 may play a role only when there is a
C V Rao et al.
Biochemical pharmacology, 42(12), 2323-2332 (1991-11-27)
A number of toxic chemicals affect the biliary excretory function of liver. Organochlorines and halomethanes are known to enhance bile flow. Despite the demonstration that a diversity of agents modify biliary function, the mechanism by which these chemicals manifest this
Z Gregus et al.
The Journal of pharmacology and experimental therapeutics, 225(2), 256-262 (1983-05-01)
Hepatic levels of uridine diphosphoglucuronic acid (UDPGA) in rats decreased substantially (greater than 80%) 40 min after galactosamine (GAL) (600 mg/kg i.p.) or after 1 hr of diethyl ether (DE) narcosis. Biliary excretion of several cholephils requiring glucuronidation before excretion
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