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Key Documents

777854

Sigma-Aldrich

Tris(hydroxypropyl)phosphine

≥80%

Synonym(s):

THPP

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About This Item

Empirical Formula (Hill Notation):
C9H21O3P
CAS Number:
Molecular Weight:
208.24
MDL number:
UNSPSC Code:
12352128
PubChem Substance ID:
NACRES:
NA.22

Assay

≥80%

form

liquid

reaction suitability

reagent type: reductant

density

1.136 g/mL at 25 °C

SMILES string

OCCCP(CCCO)CCCO

InChI

1S/C9H21O3P/c10-4-1-7-13(8-2-5-11)9-3-6-12/h10-12H,1-9H2

InChI key

YICAEXQYKBMDNH-UHFFFAOYSA-N

General description

Tris(hydroxypropyl)phosphine (THPP) is a reducing agent widely used for the reductive cleavage of disulfide bonds in small molecules in both aqueous–organic media.

Application

Tris(hydroxypropyl)phosphine can be used:
  • As a reducing agent in the reduction of dehydroascorbic acid to ascorbic acid
  • In the cleavage of disulfide bonds in small molecules
  • As a catalyst in the conversion of polysulfides

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Suttipong Suttapitugsakul et al.
Molecular bioSystems, 13(12), 2574-2582 (2017-10-12)
Mass spectrometry (MS) has become an increasingly important technique to analyze proteins. In popular bottom-up MS-based proteomics, reduction and alkylation are routine steps to facilitate peptide identification. However, incomplete reactions and side reactions may occur, which compromise the experimental results.
One-Pot Peptide Ligation-Oxidative Cyclization Protocol for the Preparation of Short-/Medium-Size Disulfide Cyclopeptides.
Spengler J, et al.
Organic Letters, 20(14), 4306-4309 (2018)
Designing dendritic polymers containing phosphorus donor ligands and their corresponding transition metal complexes.
Dasgupta M, et al.
Coordination Chemistry Reviews, 233(19), 223-235 (2002)
Tris (3-hydroxypropyl) phosphine (THPP): A mild, air-stable reagent for the rapid, reductive cleavage of small-molecule disulfides.
McNulty J, et al.
Bioorganic & Medicinal Chemistry Letters, 25(19), 4114-4117 (2015)
Hairong Wang et al.
Biomaterials, 181, 310-317 (2018-08-11)
Tumor hypoxia is known to be one of critical factors that aggravate the tumor resistance to photodynamic therapy (PDT) in which oxygen is essential for tumor destruction. Herein, catalase, an enzyme to trigger hydrogen peroxide (H2O2) decomposition, is modified by

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