71030-37-0

Basic information

• Product Name: (+/-)12-HETE
• Synonyms: (+/-)12-HYDROXYEICOSA-5Z,8Z,10E,14Z-TETRAENOIC ACID;(+/-)12-HYDROXY-5Z,8Z,10E,14Z-EICOSATETRAENOIC ACID;(+/-)12-HETE;10,14-eicosatetraenoicacid,12-hydroxy-,(e,z,z,z)-8;12-hydroxyeicosatetraenoicacid;(5E,8Z,10Z,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid;(5Z,8Z,10E,14Z)-12-Hydroxy-5,8,10,14-icosatetraenoic acid;(5Z,8Z,10E,14Z)-12-Hydroxyicosa-5,8,10,14-tetraenoic acid
• CAS NO: 71030-37-0
• Molecular Formula: C20H32O3
• Molecular Weight: 320.47
• Mol File: 71030-37-0.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 464.5 °C at 760 mmHg
• Flash Point: 155.7 °C
• Appearance: /
• Density: 0.983 g/cmºC
• Refractive Index: 1.513
• PKA: 4.75±0.10(Predicted)
• CAS DataBase Reference: (+/-)12-HETE(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)12-HETE(71030-37-0)
• EPA Substance Registry System: (+/-)12-HETE(71030-37-0)

Safety Data

• Hazardous Substances Data: 71030-37-0(Hazardous Substances Data)

Usage

Description

(±)12-HETE is one of the six monohydroxy fatty acids produced by the non-enzymatic oxidation of arachidonic acid. The biological activity of (±)12-HETE is similar to that of its constituent enantiomers (Item Nos. 34560 and 34570). It aggregates neutrophils with an EC50 value of 40 nM.

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/h6-9,11-12,15,18-19,21H,2-5,10,13-14,16-17H2,1H3,(H,22,23)

Upstream product

• 95646-01-8 (6Z,10E,12Z,15Z)-19-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-nonadeca-6,10,12,15-tetraen-9-ol 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 95645-98-0 Tributyl-[(1Z,4Z)-8-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-octa-1,4-dienyl]-stannane 
• 129030-85-9 (+/-)-(5Z)-5-undecen-1-yn-3-ol 
• 95646-00-7 (6Z,10E,12Z,15Z)-19-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-nonadeca-6,10,12,15-tetraen-9-one 
• 95645-99-1 (Z)-Undec-5-en-1-yn-3-one 
• 31823-43-5 (Z)-3-nonenal 
• 331965-16-3 cis-11,12-epoxyeicosatrienoic acid methyl ester 
• 73799-05-0 (5Z,8Z)-10-[3-((2S,3S)-3-Bromo-2-hydroxy-octyl)-oxiranyl]-deca-5,8-dienoic acid methyl ester 
• 73799-08-3 (5Z,8Z)-10-[3-(3-Pentyl-oxiranylmethyl)-oxiranyl]-deca-5,8-dienoic acid methyl ester 
• 197508-63-7 14,15-Epoxyeicosatrienoic acid methylester 
• 73799-09-4 (5Z,8Z)-10-[3-(3-Pentyl-oxiranylmethyl)-oxiranyl]-deca-5,8-dienoic acid 
• 100311-67-9 (5Z,8Z,10E,14Z)-12-(tert-Butyl-diphenyl-silanyloxy)-icosa-5,8,10,14-tetraenoic acid methyl ester 
• 100311-65-7 1-bromo-6-<(tert-butyldiphenylsilyl)oxy>-2,4,8-tetradecatriene 

Relevant articles and documents

Repurposing Resveratrol and Fluconazole to Modulate Human Cytochrome P450-Mediated Arachidonic Acid Metabolism

Cytochrome P450 (P450) enzymes metabolize arachidonic acid (AA) to several biologically active epoxyeicosatrienoic acids (EETs) and hydroxyeicosatetraenoic acids (HETEs). Repurposing clinically-approved drugs could provide safe and readily available means

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 SHORT, THREE-COMPONENT TOTAL SYNTHESIS OF 12-HYDROXYEICOSA-5,8,14(Z),10(E)-TETRAENOIC ACID (12-HETE) VIA THE CORRESPONDING KETONE

A highly effective synthesis of (+/-)-12-HETE (1) from the componenets 2, 3, and 6 is desribed which employs a new class of cuprate reagents.