(5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid

Base Information

• Chemical Name: (5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid
• CAS No.: 91712-41-3
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• Metabolomics Workbench ID: 2787
• Wikidata: Q76286014
• Mol file: 91712-41-3.mol

Synonyms:15-iso-LGE2;(5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid;(8S,12R)-10,11-seco-9,11-dioxo-15S-hydroxy-5Z,13E-prostadienoic acid;LMFA03100008

Chemical Property of (5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid

Chemical Property:

• Vapor Pressure: 5.28E-14mmHg at 25°C
• Boiling Point: 541.9°Cat760mmHg
• Flash Point: 295.6°C
• PSA: 91.67000
• Density: 1.056g/cm³
• LogP: 3.70530
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 15
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 453

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC(C=O)C(CC=CCCCC(=O)O)C(=O)C)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@@H](C=O)[C@H](C/C=C\CCCC(=O)O)C(=O)C)O

Technology Process of (5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid

There total 17 articles about (5Z,8S,9R,10E,12S)-8-acetyl-9-formyl-12-hydroxyheptadeca-5,10-dienoic acid 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:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → levuglandin LGD2 (91712-41-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium phosphate buffer, O₂ / ethanol / 0.05 h / 25 °C / microsomes, pH 7.8

2: dimethylsulfoxide-d6 / 1.42 h / 37 °C

With sodium phosphate buffer; oxygen; In dimethylsulfoxide-d6; ethanol;

DOI:10.1021/ja00332a049

Reference yield:

prostaglandin H2 (42935-17-1,127969-05-5) → levuglandin LGD2 (91712-41-3) + levuglandin LGE2 (91712-44-6)

Guidance literature:

In dimethylsulfoxide-d6; at 37 ℃; for 1.41667h; Yield given. Yields of byproduct given;

DOI:10.1021/ja00332a049

Reference yield:

methyl (5Z)-7-bromo-5-heptenoate (51751-83-8) → levuglandin LGD2 (91712-41-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1) NaH

2: NaH

3: MgBr₂

4: 1) aq. NaOH, 2) HCl

5: 1) aq. AcOH, 2) NaIO₄

With hydrogenchloride; sodium hydroxide; sodium periodate; sodium hydride; acetic acid; magnesium bromide;

DOI:10.1021/ja00338a050

upstream raw materials:

(5Z,10E)-(8R,9R,12S)-8-Acetyl-9-((R)-1,2-dihydroxy-ethyl)-12-hydroxy-heptadeca-5,10-dienoic acid

8(R)-acetyl-9(R)-<1(R),2-(isopropylidenedioxy)-ethyl>-12(S)-hydroxy-5(Z),10(E)-heptadecadienoic acid

methyl 8(R)-acetyl-9(R)-<1(R),2-(isopropylidenedioxy)-ethyl>-12(S)-hydroxy-5(Z),10(E)-heptadecadienoate

methyl 8(R)-acetyl-9(R)-<1(R),2-(isopropylidenedioxy)-ethyl>-12(S)-(tert-butyldimethylsiloxy)-5(Z),10(E)-heptadecadienoate

Downstream raw materials:

anhydro levuglandin E₂

8(R)-acetyl-9-formyl-12(S)-hydroxy-5(Z),9(E)-heptadecadienoic acid

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