12-Hydroxy-5,8,10 heptadecatrienoic acid

Base Information

• Chemical Name: 12-Hydroxy-5,8,10 heptadecatrienoic acid
• CAS No.: 50683-78-8
• Molecular Formula: C₁₇H₂₈O₃
• Molecular Weight: 280.408
• Mol file: 50683-78-8.mol

Synonyms:12-Hht;Hydroxyheptadecatrienoic acid;12-hydroxy-5,8,10 heptadecatrienoic acid

Chemical Property of 12-Hydroxy-5,8,10 heptadecatrienoic acid

Chemical Property:

• Vapor Pressure: 4.64E-10mmHg at 25°C
• Boiling Point: 451.8°C at 760 mmHg
• Flash Point: 241.1°C
• PSA: 57.53000
• Density: 0.992g/cm³
• LogP: 4.24120
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 12
• Exact Mass: 280.20384475
• Heavy Atom Count: 20
• Complexity: 316

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC=CCC=CCCCC(=O)O)O

Technology Process of 12-Hydroxy-5,8,10 heptadecatrienoic acid

There total 47 articles about 12-Hydroxy-5,8,10 heptadecatrienoic 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: 90.0%

(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid methyl ester (79171-56-5) → 12-HHT (50683-78-8,54397-84-1,64234-42-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water;

DOI:10.1055/s-0033-1338961

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → Malondialdehyde (542-78-9) + (5Z,8Z,10Z)-12-Hydroxy-heptadeca-5,8,10-trienoic acid (50683-78-8,54397-84-1,64234-42-0)

Guidance literature:

With calcimycin; disodium hydrogenphosphate; potassium dihydrogenphosphate; platelet suspension of pig blood; In water; dimethyl sulfoxide; at 37 ℃; Kinetics; Mechanism; also with additives;

DOI:10.1002/(SICI)1521-4184(199811)331:11<359::AID-ARDP359>3.0.CO;2-B

Reference yield:

(S)-(E)-(+)-1-Iodo-1-octen-3-ol (39647-93-3) + C20H37BO2 → 12-HHT (50683-78-8,54397-84-1,64234-42-0)

Guidance literature:

(S)-(E)-(+)-1-Iodo-1-octen-3-ol; C₂₀H₃₇BO₂; With tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium hydroxide; In tetrahydrofuran; water; at 40 ℃; Inert atmosphere;

In tetrahydrofuran; water; pH=5;

DOI:10.1039/c6ob02141g

upstream raw materials:

(R)-1ξ-iodo-oct-1-en-3-ol

ester methylique du 12-HHT

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

(5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid methyl ester

Downstream raw materials:

12-(S)-hydroxy-(5E,8E,10E)-heptadecatrienoic acid

hydroxyheptadeca-5Z,8E,10E-trienoicacid

Refernces

• 1、 Kobayashi, Yuichi,Morita, Masao,Ogawa, Narihito,Kondo, Daiki,Tojo, Toshifumi. "Asymmetric synthesis of 12-hydroxyheptadecatrienoic acid and its 5,6-dihydro- and 14,15-dehydro-derivatives". . p. 10667 - 10673. Retrieved 2016/11/30.
• 2、 Dannhardt, Gerd,Flemmer, Linda,Hartmann, Rolf W.,Kleber, Alice,Schulze, Elfriede. "Spectrofluorimetric quantification of malondialdehyde for evaluation of cyclooxygenase-1/Thromboxane synthase inhibition". . p. 359 - 364. Retrieved 2007/10/03.