79516-82-8

Basic information

• Product Name: (5S,12R)-5,12,20-TRIHYDROXY-(6Z,8E,10E,14Z)-EICOSATETRAENOIC ACID
• Synonyms: 20-OH-LTB4;20-HYDROXYLEUKOTRIENE B4;5S,12R,20-TRIHYDROXY-6Z,8E,10E,14Z-EICOSATETRAENOIC ACID;(5S,12R)-5,12,20-TRIHYDROXY-(6Z,8E,10E,14Z)-EICOSATETRAENOIC ACID;hydroxyleukotriene B4;(5R,12S,6Z,8E,10E,14Z)-5,12,20-Trihydroxy-6,8,10,14-icosatetraenoic acid;PTJFJXLGRSTECQ-PSPARDEHSA-N
• CAS NO: 79516-82-8
• Molecular Formula: C20H32O5
• Molecular Weight: 352.47
• Mol File: 79516-82-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 581.8°C at 760 mmHg
• Flash Point: 319.7°C
• Appearance: /
• Density: 1.097g/cm³
• Vapor Pressure: 5.84E-16mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: −20°C
• CAS DataBase Reference: (5S,12R)-5,12,20-TRIHYDROXY-(6Z,8E,10E,14Z)-EICOSATETRAENOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (5S,12R)-5,12,20-TRIHYDROXY-(6Z,8E,10E,14Z)-EICOSATETRAENOIC ACID(79516-82-8)
• EPA Substance Registry System: (5S,12R)-5,12,20-TRIHYDROXY-(6Z,8E,10E,14Z)-EICOSATETRAENOIC ACID(79516-82-8)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN 1170 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 79516-82-8(Hazardous Substances Data)

Usage

Uses

20-OH-LTB4 is a chemotactic agent for polymorphonuclear leukocytes.

Definition

ChEBI: The 20-hydroxy derivative of leukotriene B4.

InChI:InChI=1/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1

Upstream product

• 129594-38-3 5(S),12(R),20-tris<(tert-butyldimethylislyl)oxy>-6(Z),8(E),10(E),14(Z)-eicosatetraenoic acid 
• 89682-37-1 Benzoic acid (2Z,4E,6E,10Z)-(1S,8R)-1-(3-ethoxycarbonyl-propyl)-8,16-dihydroxy-hexadeca-2,4,6,10-tetraenyl ester 
• 106027-32-1 (6Z,8E,10E,14Z)-(5S,12R)-5,12,20-Tris-(tert-butyl-diphenyl-silanyloxy)-icosa-6,8,10,14-tetraenoic acid methyl ester 
• 82493-58-1 ethyl 2-O benzoyl-3,4,5-trideoxy-L-glycero-hexuronate 
• 53036-80-9 6-carboxy hexylidene triphenylphosphorane 
• 85593-68-6 (Z)-(R)-2-(tert-Butyl-diphenyl-silanyloxy)-10-hydroxy-dec-4-enal 
• 85593-69-7 (2E,6Z)-(R)-4-(tert-Butyl-diphenyl-silanyloxy)-12-hydroxy-dodeca-2,6-dienal 
• 89682-35-9 (Z)-(2S,3R)-3-(tert-Butyl-diphenyl-silanyloxy)-undec-5-ene-1,2,11-triol 
• 85593-67-5 (Z)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-6-en-1-ol 
• 85593-61-9 (Z)-(R)-9-(tert-Butyl-diphenyl-silanyloxy)-9-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-non-6-enoic acid 
• 111-29-5 1 ,5-pentanediol 
• 67133-88-4 5-iodo-1-pentanol 
• 6026-86-4 methyl 4-formylbutanoate 
• 106027-24-1 (R)-2,10-Bis-(tert-butyl-diphenyl-silanyloxy)-dec-4-yn-1-ol 

Relevant articles and documents

Highly Stereocontrolled Total Synthesis of Leukotriene B4, 20-Hydroxyleukotriene B4, Leukotriene B3, and Their Analogues

A highly stereocontrolled and practical new method for synthesis of LTB4 (1), 20-OH-LTB4 (2), and LTB3 (3) has been developed, which uses the palladium catalyzed coupling reaction of the vinylborane 5, derived from the C(1)-C(9) fragment 4, with the corresponding C(10)-C(20) fragments 6a-c.The acetylene 4 was synthesized by palladium-copper-catalyzed coupling reaction of (trimethylsilyl)acetylene with the bromide 12, which was prepared from γ-(trimethylsilyl)allylic alcohol (S)-10 by bromination followed by debromosilylation.The alcohol (S)-10 was obtained by the kinetic resolution of the racemate dl-10 using the Sharpless reagent.The vinyl iodides 6a and 6b were prepared from racemic γ-(trimethylsilyl)allylic alcohols dl-17 and dl-28, respectively, by the Sharpless kinetic resolution followed by the reactions taking advantage of the reactivity of vinylsilane moiety, while the segment 6c was prepared by the Sharpless kinetic resolution of racemic γ-iodoallylic alcohol dl-34 followed by protection.By using this method, precursors of the radiolabeled LTB4, and 20-OH-LTB4, i.e., 14,15-didehydro-LTB4 (40) and 14,15-didehydro-20-OH-LTB4 (41), respectively, were also synthesized.Similarly the novel structural analogue of LTB 42-44 were prepared.

STEREOSPECIFIC SYNTHESIS OF TWO METABOLITES OF LTB4

The stereospecific synthesis of the recently identified metabolites of LTB4 1: 5(S),12(R),20-trihydroxy-6-cis,8,10-trans,14-cis-eicosatetraenoic acid 2 and 5(S),12(R),dihydroxy-6-cis,8,10-trans,14-cis-eicosatetraen-1,20-dioic acid 3, via the synthon 4 has been accomplished; identity of synthetic and natural products has been confirmed.