12(S)-Hete

Base Information

• Chemical Name: 12(S)-Hete
• CAS No.: 54397-83-0
• Molecular Formula: C20H32O3
• Molecular Weight: 320.472
• Hs Code.: 2918199090
• UNII: WG8M7C9ALT
• DSSTox Substance ID: DTXSID001028839
• Nikkaji Number: J356.353G
• Wikipedia: 12-Hydroxyeicosatetraenoic_acid
• Wikidata: Q2823198
• Pharos Ligand ID: R3151SSJBKBS
• Metabolomics Workbench ID: 2633
• ChEMBL ID: CHEMBL1526258
• Mol file: 54397-83-0.mol

Synonyms:12 S Hydroxyeicosatetraenoic Acid;12-HETE;12-Hydroxy-5,8,10,14-eicosatetraenoic Acid;12-R-HETE;12-S-HETE;12-S-Hydroxyeicosatetraenoic Acid;Acid, 12-S-Hydroxyeicosatetraenoic

Chemical Property of 12(S)-Hete

Chemical Property:

• Vapor Pressure: 1.48E-11mmHg at 25°C
• Refractive Index: 1.513
• Boiling Point: 487.7 °C at 760 mmHg
• PKA: 4.75±0.10(Predicted)
• Flash Point: 262.8 °C
• PSA: 57.53000
• Density: 0.984 g/cm³
• LogP: 5.18750
• Storage Temp.: −20°C
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 320.23514488
• Heavy Atom Count: 23
• Complexity: 392

Purity/Quality:

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

12(S)-Hydroxy-(5Z,8Z,10E,14Z)-eicosatetraenoic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,Xi
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 7-16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC(C=CC=CCC=CCCCC(=O)O)O
• Isomeric SMILES: CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O)O
• Description: 12(S)-HETE is the predominant lipoxygenase product of mammalian platelets. It enhances tumor cell adhesion to endothelial cells, fibronectin, and the subendothelial matrix at 0.1 μM.12(S)-HETE MaxSpec? standard is a quantitative grade standard of 12(S)-HETE that has been prepared specifically for mass spectrometry or any application where quantitative reproducibility is required. The solution has been prepared gravimetrically and is supplied in a deactivated glass ampule sealed under argon. The concentration was verified by comparison to an independently prepared calibration standard. This 12(S)-HETE MaxSpec? standard is guaranteed to meet identity, purity, stability, and concentration specifications and is provided with a batch-specific certificate of analysis. Ongoing stability testing is performed to ensure the concentration remains accurate throughout the shelf life of the product. Note: The amount of solution added to the vial is in excess of the listed amount. Therefore, it is necessary to accurately measure volumes for preparation of calibration standards. Follow recommended storage and handling conditions to maintain product quality.
• Uses: A fatty acid metabolite of arachidonic acid (A765000). Potential biomarker for asthma monitoring and diagnosis. Stimulates protein kinase C-mediated release of cathepsin B from malignant cells. Used in the study of mechanisms controlling cell cycle arrest and induction of apoptosis in prostate cancer cells via 12-lipoxygenase inhibition.. 12(S)-HETE is the predominant lipoxygenase product of mammalian platelets. It enhances tumor cell adhesion to endothelial cells, fibronectin, and the subendothelial matrix at 0.1 μM.

Technology Process of 12(S)-Hete

There total 65 articles about 12(S)-Hete 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: 95.0%

(S)-methyl (5Z,8Z,10E,14Z)-12-hydroxyeicosa-5,8,10,14-tetraenoate (57872-14-7) → 12-hydroxyeicosatetraenoic acid (54397-83-0,59985-28-3)

Guidance literature:

With lithium hydroxide; In 1,2-dimethoxyethane; water; Ambient temperature;

DOI:10.1021/jo00356a004

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → thromboxane B2 (54397-85-2) + dinoprostone (363-24-6) + 12-hydroxyeicosatetraenoic acid (54397-83-0,59985-28-3)

Guidance literature:

With microsomes of mutton vesicular glands; oxygen; In octane; water; at 25 ℃; for 1h; Product distribution; potassium phosphate buffer (pH 7.4) presence, n-octane absence;

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → 12-hydroxyeicosatetraenoic acid (54397-83-0,59985-28-3) + (R)-12-HETE (82337-46-0) + 8(S)-hydroxyeicosatetraenoic acid (98462-03-4,79495-84-4) + (8R)-hydroxyeicosatetraenoic acid (105500-09-2,79495-84-4) + (R)-11-hydroxy-eicosa-5,8,12,14-tetraenoic acid (73347-43-0,73804-65-6) + icomucret (54845-95-3,73945-47-8,83603-31-0) + 15(R)-HETE (73945-47-8,83603-31-0) + (S)-11-hydroxy-eicosa-5,8,12,14-tetraenoic acid (54886-50-9,73804-65-6)

Guidance literature:

all cis 5,8,11,14-eicosatetraenoic acid; With 8R-lipoxygenase A₅₈₉M mutant; sodium chloride; calcium chloride; In ethanol; at 20 ℃; pH=8; Enzymatic reaction;

With triphenylphosphine; In methanol; at 20 ℃; for 0.5h; Reagent/catalyst; Kinetics;

DOI:10.1074/jbc.M114.599662

upstream raw materials:

(S)-methyl (5Z,8Z,10E,14Z)-12-hydroxyeicosa-5,8,10,14-tetraenoate

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

7-carbomethoxy hepta-3-(Z)-en-1-ylidenetriphenylphosphorane

((3Z)-7-methoxycarbonyl-3-heptenyl)-triphenylphosphonium iodide

Refernces

• 1、 Neau, David B.,Bender, Gunes,Boeglin, William E.,Bartlett, Sue G.,Brash, Alan R.,Newcomer, Marcia E.. "Crystal structure of a lipoxygenase in complex with substrate: The arachidonic acid-binding site of 8R-lipoxygenase". . p. 31905 - 31913. Retrieved 2015/02/19.
• 2、 Rodríguez,Nomen,Spur,Godfroid,Lee. "Total synthesis of 12(R)-HETE, 12(S)-HETE, 2H2-12(R)-HETE and LTB4 from racemic glycidol via hydrolytic kinetic resolution". . p. 25 - 37. Retrieved 2007/10/03.