5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)-

Base Information

• Chemical Name: 5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)-
• CAS No.: 54397-84-1
• Molecular Formula: C₁₇H₂₈O₃
• Molecular Weight: 280.408
• Hs Code.: 2918199090
• European Community (EC) Number: 633-391-7
• Nikkaji Number: J410.721G,J2.564.026H,J1.779.334I
• Wikipedia: 12-Hydroxyheptadecatrienoic_acid
• Mol file: 54397-84-1.mol

Synonyms:5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)-;64234-42-0;54397-84-1;(12S)-12-Hydroxy-5,8,10-heptadecanetrienoic acid;(5E,8E,10E,12S)-12-Hydroxy-5,8,10-heptadecatrienoic acid;(5Z,8E,10E,12S)-12-Hydroxy-5,8,10-heptadecatrienoic acid

Chemical Property of 5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)-

Chemical Property:

• Vapor Pressure: 4.64E-10mmHg at 25°C
• Melting Point: 151.79 (Mean or Weighted MP)oC
• Refractive Index: 1.506
• Boiling Point: 451.8 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 241.1 °C
• PSA: 57.53000
• Density: 0.992 g/cm³
• LogP: 4.24120
• Storage Temp.: −20°C
• 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:

99% ^*data from raw suppliers

12(S)-HHTrE ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC=CCC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/C=C/C/C=C/CCCC(=O)O)O
• Uses: 12(S)-HHTrE is an unusual product of the cyclooxygenase (COX) pathway and one of the primary arachidonic acid metabolites of the human platelet. It is biosynthesized by thromboxane synthase (TX synthase) from prostaglandin H2 (PGH2) concurrently with TXA2. The biological role of 12(S)-HHTrE is uncertain. It is avidly oxidized to 12-oxoHTrE by porcine 15-hydroxy PGDH. 12(S)-HHTrE is a metabolite of arachidonic acid (A765000), which is an essential fatty acid and a precursor in the biosynthesis of prostaglandins, thromboxanes, and leukotrienes. Arachidonic Acid occurs in liver, brain, glandular organs, and depot fats of animals, in small amounts in human depot fats, and Arachidonic Acid is also a constituent of animal phosphatides.

Technology Process of 5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)-

There total 80 articles about 5,8,10-Heptadecatrienoic acid, 12-hydroxy-, (S)- 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: 90.0%

C33H46O3Si → C17H28O3 (54397-84-1,64234-42-0)

Guidance literature:

With tetrabutyl ammonium fluoride;

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

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、 Tojo, Toshifumi,Wang, Qian,Okuno, Toshiaki,Yokomizo, Takehiko,Kobayashi, Yuichi. "Synthesis of (S,5 Z,8 E,10 E)-12-hydroxyheptadeca-5,8,10-trienoic acid (12 S -HHT) and its analogues". . p. 1545 - 1548. Retrieved 2013/08/23.
• 2、 John,Schlegel. "Thermodynamic and structural characterization of cis-trans isomerization of 12-(S)-hydroxy-(5Z, 8E,10E)-heptadecatrienoic acid by high-performance liquid chromatography and gaschromatography-mass spectrometry". . p. 181 - 188. Retrieved 2007/10/03.