54397-83-0

Basic information

• Product Name: 12(S)-HETE
• Synonyms: 12(S)-HYDROXY-(5Z,8Z,10E,14Z)-EICOSATETRAENOIC ACID;12(S)-HETE;12(S)-HYDROXYEICOSA-5Z,8Z,10E,14Z-TETRAENOIC ACID;(12S,5Z,8Z,10E,14Z)-12-Hydroxyeicosatetraenoic acid;12(S)-hydroxy-(5Z,8Z,10E,14Z)-*eicosatetraenoic A;12(S)-HYDROXY-(5Z,8Z,10E,14Z)-*EICOSATET RAENOIC ACI;(s)-12-hete;(5Z,8Z,10E,12S,14Z)-12-Hydroxy-5,8,10,14-icosatetraenoic acid
• CAS NO: 54397-83-0
• Molecular Formula: C₂₀H₃₂O₃
• Molecular Weight: 320.47
• EINECS: 200-578-6
• Product Categories: Aliphatics;Fatty Acid Derivatives & Lipids;Glycerols;Metabolites & Impurities
• Mol File: 54397-83-0.mol

Chemical Properties

• Boiling Point: 487.7 °C at 760 mmHg
• Flash Point: 14 °C
• Appearance: /
• Density: 0.984 g/cm³
• Vapor Pressure: 1.48E-11mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: −20°C
• PKA: 4.75±0.10(Predicted)
• BRN: 2656104
• CAS DataBase Reference: 12(S)-HETE(CAS DataBase Reference)
• NIST Chemistry Reference: 12(S)-HETE(54397-83-0)
• EPA Substance Registry System: 12(S)-HETE(54397-83-0)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 7-16-26-36
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 1
• F: 8-10-23
• Hazardous Substances Data: 54397-83-0(Hazardous Substances Data)

Usage

Uses

1. Used in Asthma Monitoring and Diagnosis:
12(S)-HETE is used as a potential biomarker for asthma monitoring and diagnosis, aiding in the early detection and management of the condition.
2. Used in Cancer Research:
12(S)-HETE is used as a research tool for studying mechanisms controlling cell cycle arrest and the induction of apoptosis in prostate cancer cells via 12-lipoxygenase inhibition. It also stimulates protein kinase C-mediated release of cathepsin B from malignant cells, contributing to the understanding of cancer cell behavior.
3. Used in Tumor Cell Adhesion Studies:
In the field of cancer research, 12(S)-HETE is used as a compound to enhance tumor cell adhesion to endothelial cells, fibronectin, and the subendothelial matrix at 0.1 μM, providing insights into cancer cell interactions and metastasis.
4. Used in Mass Spectrometry and Quantitative Applications:
12(S)-HETE MaxSpec standard is a quantitative grade standard of 12(S)-HETE prepared specifically for mass spectrometry or any application where quantitative reproducibility is required. It ensures accurate concentration measurements and is supplied with a batch-specific certificate of analysis, making it a valuable tool in various scientific and medical research applications.

Biochem/physiol Actions

12(S)-HETE is a bioactive lipid implicated in angiogenesis, growth, and metastasic action in tumor cell lines and in animal models. Arachidonate 12-lipoxygenase (12-LOX) converts arachidonic acid to 12(S)-(HETE). Alteration in 12-LOX expression or activity has been reported in various carcinomas including prostate carcinoma.

InChI:InChI=1/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1

Upstream product

• 57872-14-7 (S)-methyl (5Z,8Z,10E,14Z)-12-hydroxyeicosa-5,8,10,14-tetraenoate 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 109296-17-5 7-carbomethoxy hepta-3-(Z)-en-1-ylidenetriphenylphosphorane 
• 91097-63-1 ((3Z)-7-methoxycarbonyl-3-heptenyl)-triphenylphosphonium iodide 
• 245326-04-9 (S,Z)-O-(triethylsilyl)-2-hydroxydec-4-enal 
• 245325-96-6 (S,4Z)-1,2-O-bis(triethylsilyl)dec-4-en-1,2-diol 
• 329896-88-0 (S)-2-[(triethylsilyl)oxy]-4-decynal 
• 329896-86-8 (S)-1-[(triethylsilyl)oxy]-4-decyn-2-ol 
• 329896-98-2 (S)-4-[(triethylsilyl)oxy]-2(E),6(Z)-dodecadienal 
• 329896-90-4 (S)-4-[(triethylsilyl)oxy]-2(E)-dodecen-6-ynal 
• 329896-87-9 (S)-1,2-bis[(triethylsilyl)oxy]-4-decyne 
• 329896-94-8 (S)-12-[(triethylsilyl)oxy]-5(Z),8(Z),10(E),14(Z)-eicosatetraenoic acid methyl ester 
• 329896-92-6 (S)-12-[(triethylsilyl)oxy]-5(Z),8(Z),10(E)-eicosatrien-14-ynoic acid methyl ester 
• 291755-29-8 (E)-1-bromoundec-2-en-5-yne 

Relevant articles and documents

A short catalytic enantioselective synthesis of the proinflammatory eicosanoid 12(R)-hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoic acid (12(R)-HETE)

(equation presented) A new and effective pathway is described for the synthesis of 12(R)-HETE and the 12(S)-enantiomer from the common intermediates 4 and 8.

Crystal structure of a lipoxygenase in complex with substrate: The arachidonic acid-binding site of 8R-lipoxygenase

Lipoxygenases (LOX) play critical roles in mammalian biology in the generation of potent lipid mediators of the inflammatory response; consequently, they are targets for the development of isoform-specific inhibitors. The regio- and stereo-specificity of the oxygenation of polyunsaturated fatty acids by the enzymes is understood in terms of the chemistry, but structural observation of the enzyme-substrate interactions is lacking. Although several LOX crystal structures are available, heretofore the rapid oxygenation of bound substrate has precluded capture of the enzyme-substrate complex, leaving a gap between chemical and structural insights. In this report, we describe the 2.0 ? resolution structure of 8R-LOX in complex with arachidonic acid obtained under anaerobic conditions. Subtle rearrangements, primarily in the side chains of three amino acids, allow binding of arachidonic acid in a catalytically competent conformation. Accompanying experimental work supports a model in which both substrate tethering and cavity depth contribute to positioning the appropriate carbon at the catalytic machinery.

Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways

Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 α-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering p

Total synthesis of 12(R)-HETE, 12(S)-HETE, 2H2-12(R)-HETE and LTB4 from racemic glycidol via hydrolytic kinetic resolution

The total synthesis of 12(R)-HETE, 12(S)-HETE (Samuelsson's HETE), [14,15-2H2]-12(R)-HETE and Leukotriene B4 from racemic glycidol is described. The key steps are the hydrolytic kinetic resolution of racemic TES-glycidol with salen-Co catalyst and the selective oxidation of primary silyl ethers, in the presence of secondary ones, under Swern conditions to give a short entry to both enantiomers of 12-HETE and LTB4.

A new practical enantiospecific synthesis of unlabelled and tritium labelled 12-HETEs

The oxidative metabolism of arachidonic acid AA is known to yield a variety of biologically active substances.Among them, both enantiomers of 12-hydroxyeicosatetraenoic acid (12-HETE) have been the subject of much interest.In order to extend their biologi

Stereospecific Total Synthesis of Dimorphecolic Acid, 5(S)-HETE, and 12(S)-Hete

First enantiospecific synthesis of dimorphecolic acid is accomplished via an efficient and stereocontrolled route.The convenient synthesis of 5(S)-HETE and 12(S)-HETE is also described.

The Total Synthesis of 12-HETE and 12,20-DiHETE

The total syntheses of 12-HETE (1) in racemic form and of both enantiomers in optically pure form are reported.The synthesis of a metabolite of 12(S)-HETE, 12,20-diHETE (2), in optically pure form is also reported.

A General Strategy for the Synthesis of Monohydroxyeicosatetraenoic Acids: Total Synthesis of 5(S)-Hydroxy-6(E),8,11,14(Z)-eicosatetraenoic Acid (5-HETE) and 12(S)-Hydroxy-5,8,14(Z),10(E)-eicosatetraenoic Acid (12-HETE)

Stereocontrolled total syntheses of 5(S)-hydroxy-6(E),8,11,14(Z)-eicosatetraenoic acid (5-HETE) and 12(S)-hydroxy-5,8,14(Z),10(E)-eicosatetraenoic acid (12-HETE) via palladium(0)-copper(I) coupling technology are described.

ENANTIOSPECIFIC TOTAL SYNTHESIS OF 8- and 12-HYDROXYEICOSATETRAENOIC ACID

The R- and S-isomers of 8- and 12-hidroxyeicosatetraenoic acid (8- and 12-HETE) were synthesized from dimethyl malate derived precursors.