Butaprost

Base Information

Chemical Name:Butaprost
CAS No.:69648-38-0
Molecular Formula:C₂₄H₄₀O₅
Molecular Weight:408.579
Hs Code.:
UNII:HP16WVP23Y
DSSTox Substance ID:DTXSID8048993
Nikkaji Number:J22.802H
Wikidata:Q27075579
NCI Thesaurus Code:C74369
Pharos Ligand ID:FB1F2SK7K6BZ
ChEMBL ID:CHEMBL271896
Mol file:69648-38-0.mol

Synonyms:15-deoxy-16-hydroxy-17-cyclobutylprostaglandin E1 methyl ester;butaprost;DOH-CB-PGE1;TR 4979;TR-4979

Suppliers and Price of Butaprost

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

TRC
Butaprost
2.5mg
$ 1325.00

Sigma-Aldrich
(R)-Butaprost ≥98% (HPLC)
5mg
$ 693.00

Sigma-Aldrich
(R)-Butaprost ≥98% (HPLC)
1mg
$ 177.00

Cayman Chemical
(R)-Butaprost ≥98%
10mg
$ 951.00

Cayman Chemical
(R)-Butaprost ≥98%
1mg
$ 120.00

Cayman Chemical
(R)-Butaprost ≥98%
5mg
$ 535.00

AK Scientific
(R)-Butaprost
1mg
$ 248.00

Total 5 raw suppliers

Chemical Property of Butaprost

Chemical Property:

Vapor Pressure:3.2E-13mmHg at 25°C
Melting Point:-57oC
Boiling Point:525.1°Cat760mmHg
Flash Point:168.4°C
PSA：83.83000
Density:1.105g/cm³
LogP:4.34370
Storage Temp.:−20°C
Solubility.:DMSO: freely soluble
XLogP3:4.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:14
Exact Mass:408.28757437
Heavy Atom Count:29
Complexity:552

Purity/Quality:

98%,99%, ^*data from raw suppliers

Butaprost ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CCCC1(CCC1)C(CC=CC2C(CC(=O)C2CCCCCCC(=O)OC)O)O
Isomeric SMILES:CCCC1(CCC1)[C@@H](C/C=C/[C@H]2[C@@H](CC(=O)[C@@H]2CCCCCCC(=O)OC)O)O
Description Butaprost is a structural analog of prostaglandin E2 (PGE2) with good selectivity for the EP2 receptor subtype. Butaprost has frequently been used to pharmacologically define the EP receptor expression profile of various human and animal tissues and cells. Serious confusion as to the structure of butaprost was generated by Gardiner in 1986, when he reported that the epimer of butaprost showing this selective activity was the C-16 (R)-epimer (See reference and Note). Butaprost binds with about 1/10 the affinity of PGE2 to the recombinant murine EP2 receptor, and does not bind appreciably to any of the other murine EP receptors or DP, FP, IP, or TP receptors. The pharmacology of (R)-butaprost has not been carefully studied, but it is generally considered to be the less active epimer. (NOTE: In the Gardiner paper in the 1986 British Journal of Pharmacology, butaprost appears on page 46 where it is given the name TR 4979. The structure as drawn is incorrect, in that the author was using and referring to the more active C-16 epimer, which is actually 16(S). The structure on page 46 shows the structure as 16(R). It was not until the late 1990’s that careful studies both in the US and Japan correctly identified the actual configuration of C-16 in the compound called butaprost is 16(S).)
Uses (R)-Butaprost has been used as a prostanoid receptor (EP)-specific agonist to study its effects on protein kinase A (PKA) regulatory subunits in MCF7 cells. It may be used as EP2 agonist in Madin-Darby canine kidney and mouse cortical collecting duct (mpkCCD14) cells. It may also be used as EP2 agonist in human fetal lung fibroblasts (HFL-1) cells to test its effect on vascular endothelial growth factor (VEGF) production. Bronchodilator.

Technology Process of Butaprost

There total 12 articles about Butaprost which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 58148-14-4
2,2-trimethylenepentanoic acid

: 69648-38-0,69685-22-9
butaprost

Guidance literature:: Multi-step reaction with 6 steps

1: lithium aluminium tetrahydride / diethyl ether

2: Py*HClCrO₃ / dichloromethane

3: diethyl ether / Heating

4: (i) iBu₂AlH, toluene, (ii) I₂, THF

5: toluene-4-sulfonic acid

With lithium aluminium tetrahydride; Py*HClCrO₃; toluene-4-sulfonic acid; In diethyl ether; dichloromethane;

Reference yield:

: 58148-14-4
2,2-trimethylenepentanoic acid

: 69648-38-0,69685-22-9
Methyl-11α,16S-dihydroxy-17,17-propano-9-oxo-prost-13E-en-1-oat

Guidance literature:: Multi-step reaction with 6 steps

1: lithium aluminium tetrahydride / diethyl ether

2: Py*HClCrO₃ / dichloromethane

3: diethyl ether / Heating

4: (i) iBu₂AlH, toluene, (ii) I₂, THF

5: toluene-4-sulfonic acid

With lithium aluminium tetrahydride; Py*HClCrO₃; toluene-4-sulfonic acid; In diethyl ether; dichloromethane;

Reference yield:

: 69647-61-6
2,2-trimethylene-1-pentanol

: 69648-38-0,69685-22-9
butaprost

Guidance literature:: Multi-step reaction with 5 steps

1: Py*HClCrO₃ / dichloromethane

2: diethyl ether / Heating

3: (i) iBu₂AlH, toluene, (ii) I₂, THF

4: toluene-4-sulfonic acid

With Py*HClCrO₃; toluene-4-sulfonic acid; In diethyl ether; dichloromethane;