prostaglandin D2

Base Information

• Chemical Name: prostaglandin D2
• CAS No.: 41598-07-6
• Molecular Formula: C20H32 O5
• Molecular Weight: 352.471
• European Community (EC) Number: 636-995-9
• UNII: RXY07S6CZ2
• DSSTox Substance ID: DTXSID30897162
• Nikkaji Number: J16.416J
• Wikipedia: Prostaglandin_D2
• Wikidata: Q419750
• NCI Thesaurus Code: C116013
• Pharos Ligand ID: GCDLHWLPJTLQ
• Metabolomics Workbench ID: 2374
• ChEMBL ID: CHEMBL1235252
• Mol file: 41598-07-6.mol

Synonyms:11 Dehydroprostaglandin F2 alpha;11 Dehydroprostaglandin F2alpha;11-Dehydroprostaglandin F2 alpha;11-Dehydroprostaglandin F2alpha;alpha, 11-Dehydroprostaglandin F2;D2, Prostaglandin;F2 alpha, 11-Dehydroprostaglandin;F2alpha, 11-Dehydroprostaglandin;PGD2;Prostaglandin D2

Chemical Property of prostaglandin D2

Chemical Property:

• Vapor Pressure: 2.27E-14mmHg at 25°C
• Refractive Index: 1.6120 (estimate)
• Boiling Point: 549.6°Cat760mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 300.3°C
• PSA: 94.83000
• Density: 1.148g/cm³
• LogP: 3.25110
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly), THF (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 469

Purity/Quality:

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

Prostaglandin D2 ^*data from reagent suppliers

Safty Information:

• Hazard Codes: T
• Statements: 60-22
• Safety Statements: 53-22-26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(C(CC1=O)O)CC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@@H]1[C@H]([C@H](CC1=O)O)C/C=C\CCCC(=O)O)O
• Recent ClinicalTrials: Complementary Treatment of PG2 to Improve Clinical Benefit Response and Quality of Life in Fatigue
• Description: Prostaglandin D2 (PGD2) is the major eicosanoid product of mast cells and is released in large quantities during allergic and asthmatic anaphylaxis. Mastocytosis patients produce excessive amounts of PGD2, which causes vasodilation, flushing, hypotension, and syncopal episodes. PGD2 is also produced in the brain via an alternative pathway involving a soluble, secreted PGD-synthase also known as β-trace. In the brain, PGD2 produces normal physiological sleep and lowering of body temperature. Further pharmacological actions include inhibition of platelet aggregation and relaxation of vascular smooth muscle. PGD2 inhibits human ovarian tumor cell proliferation with an IC50 of 6.8 μM.
• Uses: Prostaglandin D2 is a fatty acid compound present in the human body. Elevated levels of localized Prostaglandin D2 has been linked to hair loss and growth inhibition. It has also been seen to contribute to the activity of allergic asthma.

Technology Process of prostaglandin D2

There total 9 articles about prostaglandin D2 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: 74.0%

(Z)-7-[(6R,7R,8S)-8-Hydroxy-6-((E)-(S)-3-hydroxy-oct-1-enyl)-1,4-dioxa-spiro[4.4]non-7-yl]-hept-5-enoic acid (87789-17-1,87789-18-2) → PGD2 (41598-07-6,54396-59-7,59894-05-2,64072-55-5,65026-03-1,65026-04-2,65026-05-3,69779-97-1)

Guidance literature:

With acetic acid; at 20 ℃; for 20h;

DOI:10.1016/S0040-4039(00)88113-7

Reference yield: 70.0%

(Z)-7-[(6R,7R,8S)-8-Hydroxy-6-((E)-(R)-3-hydroxy-oct-1-enyl)-1,4-dioxa-spiro[4.4]non-7-yl]-hept-5-enoic acid (87789-17-1,87789-18-2) → (Z)-7-[(1S,2S,5R)-5-Hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-3-oxo-cyclopentyl]-hept-5-enoic acid (41598-07-6,54396-59-7,59894-05-2,64072-55-5,65026-03-1,65026-04-2,65026-05-3,69779-97-1)

Guidance literature:

With acetic acid; at 20 ℃; for 20h;

DOI:10.1016/S0040-4039(00)88113-7

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → prostaglandin D2 (41598-07-6) + dinoprostone (363-24-6) + dinoprost (551-11-1) + 12-hydroxy-heptadecatrienoic acid

Guidance literature:

With HUV-EC-C; at 37 ℃; for 0.166667h; Further Variations:; Reagents; Enzyme kinetics; Enzymatic reaction;

DOI:10.1038/sj.bjp.0701112

upstream raw materials:

all cis 5,8,11,14-eicosatetraenoic acid

(Z)-7-[(6R,7R,8S)-8-Hydroxy-6-((E)-(S)-3-hydroxy-oct-1-enyl)-1,4-dioxa-spiro[4.4]non-7-yl]-hept-5-enoic acid

(Z)-7-[(6R,7R,8S)-8-Hydroxy-6-((E)-(S)-3-hydroxy-oct-1-enyl)-1,4-dioxa-spiro[4.4]non-7-yl]-hept-5-enoic acid methyl ester

(Z)-7-[(6R,7R,8S)-8-Hydroxy-6-((E)-(R)-3-hydroxy-oct-1-enyl)-1,4-dioxa-spiro[4.4]non-7-yl]-hept-5-enoic acid

Downstream raw materials:

PGD₂ 9,15-bis(triphenylsilyl ether)

(12E)-Δ¹²-PGD₂

(12Z)-Δ¹²-PGD₂

prostaglandin F_2α 1,11-lactone