Prostanoic acid

Base Information

• Chemical Name: Prostanoic acid
• CAS No.: 25151-81-9
• Molecular Formula: C20H38O2
• Molecular Weight: 310.51500
• Hs Code.: 2916209090
• DSSTox Substance ID: DTXSID00331427
• Nikkaji Number: J227.995I
• Wikipedia: Prostanoic_acid
• Wikidata: Q22004571
• Metabolomics Workbench ID: 53394
• Mol file: 25151-81-9.mol

Synonyms:Prostanoic acid;prostan-1-oic acid;25151-81-9;7-[(1S,2S)-2-octylcyclopentyl]heptanoic acid;7-((1S,2S)-2-Octylcyclopentyl)heptanoic acid;rel-7-((1S,2S)-2-Octylcyclopentyl)heptanoic acid;58986-83-7;Prostanoic acid skeleton;FA(20:0(cyclo));SCHEMBL126631;CHEBI:8504;DTXSID00331427;LMFA03010000;C02064;Q22004571

Chemical Property of Prostanoic acid

Chemical Property:

• PSA: 37.30000
• LogP: 6.57850
• XLogP3: 8.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 14
• Exact Mass: 310.287180451
• Heavy Atom Count: 22
• Complexity: 275

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCC1CCCC1CCCCCCC(=O)O
• Isomeric SMILES: CCCCCCCC[C@H]1CCC[C@@H]1CCCCCCC(=O)O
• Uses: Prostanoic Acid is used in the composition of Human life extension therapy through molecular, cellular and subcellular management of biochemical requirements of mitochondria and of other organelle processes associated with the advent of disease and?/or aging.

Technology Process of Prostanoic acid

There total 26 articles about Prostanoic 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: 77.0%

methyl prostanoate (61549-96-0) → PROSTANOIC ACID (25151-81-9)

Guidance literature:

With sodium hydroxide; In ethanol; at 50 ℃; for 4h;

DOI:10.1248/cpb.34.550

Reference yield:

prost-5-enoic acid (58986-86-0) → PROSTANOIC ACID (25151-81-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent

2: 78 percent / H₂ / Pt / methanol / 20 h / -20 °C

3: 77 percent / 5 percent aq. NaOH / ethanol / 4 h / 50 °C

With sodium hydroxide; hydrogen; platinum; In methanol; ethanol;

DOI:10.1248/cpb.34.550

Reference yield:

(S)-(-)-p-mentha-1,8(10)-dien-9-ol (10067-33-1) → PROSTANOIC ACID (25151-81-9)

Guidance literature:

Multi-step reaction with 24 steps

1: pyridine

2: 80 percent MCPBA / CH₂Cl₂; various solvent(s) / 4 h / Ambient temperature

3: 1 percent aq. H₂SO₄ / tetrahydrofuran / 24 h / Ambient temperature

4: NaIO₄ / H₂O; tetrahydrofuran / 0 deg C, 1 h, RT, 6 h

5: 72 percent / NaBH₄, CeCl₃*7H₂O / ethanol; H₂O / 0.17 h / -15 °C

6: 96 percent / tris(triphenylphosphine)chlororhodium / CH₂Cl₂ / 9 h / Ambient temperature

7: BF₃-etherate / CH₂Cl₂ / 3 h / Ambient temperature

8: Raney-Ni / ethanol / 5 h / Heating

9: 57 percent / CrO₃ in H₂SO₄ / acetone / 1 h / 0 - 10 °C

11: 83 percent / p-toluenesulfonic acid / benzene / 3 h / Heating

12: 83 percent / Na, MeOH / toluene / 6 h / Heating

13: 89 percent / LiAlH₄ / diethyl ether / 3 h / 0 - 5 °C

14: 40 percent / CrO₃ / pyridine; CH₂Cl₂ / 0.5 h / 0 - 5 °C

15: 1.) 15 percent BuLi / 2.) ether, 5 deg C to 10 deg C, 1 h

16: 97 percent / H₂ / Pt / methanol / 20 h / -20 °C

17: 96 percent / 10 percent HCl / methanol / 1 h / Ambient temperature

18: 89 percent / (CF₃CO)2O, 60 percent H₂O₂, Na₂HPO₄ / CH₂Cl₂ / 5 h / Ambient temperature

19: 93 percent / K₂CO₃ / methanol / 3 h / Ambient temperature

20: 70 percent / PDC / CH₂Cl₂ / 4 h / Ambient temperature

21: 1.) 60 percent NaH, DMSO / 2.) DMSO, RT, 2 h

22: 90 percent

23: 78 percent / H₂ / Pt / methanol / 20 h / -20 °C

24: 77 percent / 5 percent aq. NaOH / ethanol / 4 h / 50 °C

With pyridine; chromium(VI) oxide; hydrogenchloride; methanol; sodium hydroxide; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; lithium aluminium tetrahydride; dipyridinium dichromate; Jones’ reagent; n-butyllithium; cerium(III) chloride; sulfuric acid; boron trifluoride diethyl etherate; hydrogen; dihydrogen peroxide; sodium; nickel; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic anhydride; Wilkinson's catalyst; platinum; In tetrahydrofuran; pyridine; methanol; diethyl ether; ethanol; dichloromethane; water; acetone; toluene; benzene;

DOI:10.1248/cpb.34.550

upstream raw materials:

methyl prostanoate

prost-5-enoic acid

(S)-(-)-p-mentha-1,8⁽¹⁰⁾-dien-9-ol

(1R,2R)-1-3-<(3ξ)-3-hydroxybutyl>-2-hydroxymethylcyclopentane

Refernces

• 1、 Suemune,Kawahara,Sakai. "Conversion of limonene to prostanoic acid and 8-isoprostanoic acid". . p. 550 - 557. Retrieved 2007/10/02.