71160-24-2 Usage
Description
Different sources of media describe the Description of 71160-24-2 differently. You can refer to the following data:
1. Leukotriene B4 (LTB4) is a dihydroxy fatty acid derived from arachidonic acid through the 5-LO pathway. It promotes a number of leukocyte functions including aggregation, stimulation of ion fluxes, enhancement of lysosomal enzyme release, superoxide anion production, chemotaxis, and chemokinesis. In subnanomolar ranges (3.9 x 10?10 M), LTB4 causes chemotaxis and chemokinesis in human polymorphonuclear leukocytes. At higher concentrations, (1.0 x 10?7 M), LTB4 leads to neutrophil aggregation and degranulation as well as superoxide anion production.
2. Leukotriene B4 (LTB4) is a dihydroxy fatty acid derived from arachidonic acid through the 5-LO pathway. It promotes a number of leukocyte functions including aggregation, stimulation of ion fluxes, enhancement of lysosomal enzyme release, superoxide anion production, chemotaxis, and chemokinesis. In subnanomolar ranges (3.9 x 10?10 M), LTB4 causes chemotaxis and chemokinesis in human polymorphonuclear leukocytes. At higher concentrations, (1.0 x 10?7 M), LTB4 leads to neutrophil aggregation and degranulation as well as superoxide anion production. LTB4 MaxSpec? standard is a quantitative grade standard of LTB4 that has been prepared specifically for mass spectrometry and related applications 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 LTB4 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
LTB4 (Leukotriene B4) is a potent chemokine with roles in inflammation, immunology, the nervous system, brain and skin.
Definition
ChEBI: A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents.
Biological Activity
Potent lipid inflammatory mediator derived from the 5-lipoxygenase pathway of arachidonic acid metabolism. Binds to BLT 1 and BLT 2 receptors and acts as a potent chemotactic agent and activator of leukocytes. Also displays antiviral activity towards DNA viruses and retroviruses.
Biochem/physiol Actions
Proinflammatory agent. Stimulates c-Fos and c-Jun proto-oncogene transcription in human monocytes. Stimulates chemotaxis, aggregation, and degranulation of polymorphonuclear leukocytes.
Check Digit Verification of cas no
The CAS Registry Mumber 71160-24-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 7,1,1,6 and 0 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 71160-24:
(7*7)+(6*1)+(5*1)+(4*6)+(3*0)+(2*2)+(1*4)=92
92 % 10 = 2
So 71160-24-2 is a valid CAS Registry Number.
InChI:InChI=1/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7-,9-6-,14-10+,15-11+/t18-,19-/m1/s1
71160-24-2Relevant articles and documents
Stereocontrolled total synthesis of leukotriene B4
Avignon-Tropis,Berjeaud,Pougny,Frechard-Ortuno,Guillerm,Linstrumelle
, p. 651 - 654 (1992)
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Catalytic asymmetric synthesis of Leukotriene B4
Yang, Pengfei,Zhong, Jiangchun,Ji, Kaijie,Yin, Jingwei,Li, Shuoning,Wei, Siyuan,Zhou, Yun,Wang, Lifeng,Wang, Min,Bian, Qinghua
, p. 1596 - 1601 (2017/10/20)
Leukotriene B4 1 was prepared from two chiral synthons 8 and 14. The chiral secondary alcohols of 8 and 14 were constructed by BINOL/Ti(OiPr)4 catalyzed enantioselective alkynylzinc addition to aldehydes.
COX-2-dependent and -independent biosynthesis of dihydroxy-arachidonic acids in activated human leukocytes
Tejera, Noemi,Boeglin, William E.,Suzuki, Takashi,Schneider, Claus
scheme or table, p. 87 - 94 (2012/03/26)
Biosynthesis of 5,15-dihydroxyeicosatetraenoic acid (5,15-diHETE) in leukocytes involves consecutive oxygenation of arachidonic acid by 5-lipoxygenase (LOX) and 15-LOX in either order. Here, we analyzed the contribution of cyclooxygenase (COX)-2 to the biosynthesis of 5,15-di-HETE and 5,11-diHETE in isolated human leukocytes activated with lipopolysaccharide and calcium ionophore A23187. Transformation of arachidonic acid was initiated by 5-LOX providing 5 S -HETE as a substrate for COX-2 forming 5 S,15 S -diHETE, 5 S,15 R -diHETE, and 5 S,11 R -di-HETE as shown by LC/MS and chiral phase HPLC analyses. The levels of 5,15-diHETE were 0.45 ± 0.2 ng/106 cells (mean ± SEM, n = 6), reaching about half the level of LTB 4 (1.3 ± 0.5 ng/106 cells, n = 6). The COX-2 specific inhibitor NS-398 reduced the levels of 5,15-diHETE to below 0.02 ng/106 cells in four of six samples. Similar reduction was achieved by MK-886, an inhibitor of 5-LOX activating protein but the above differences were not statistically significant. Aspirin treatment of the activated cells allowed formation of 5,15-diHETE (0.1 ± 0.05 ng/106 cells, n = 6) but, as expected, abolished formation of 5,11-diHETE. The mixture of activated cells also produced 5 S,12 S -diHETE with the unusual 6 E,8 Z,10 E double bond configuration, implicating biosynthesis by 5-LOX and 12-LOX activity rather than by hydrolysis of the leukotriene A 4 -epoxide. Exogenous octadeuterated 5 S -HETE and 15 S -HETE were converted to 5,15-diHETE, implicating that multiple oxygenation pathways of arachidonic acid occur in activated leukocytes. The contribution of COX-2 to the biosynthesis of dihydroxylated derivatives of arachidonic acid provides evidence for functional coupling with 5-LOX in activated human leukocytes. Copyright
An atom-economic and selective ruthenium-catalyzed redox isomerization of propargylic alcohols. An efficient strategy for the synthesis of leukotrienes
Trost, Barry M.,Livingston, Robert C.
supporting information; experimental part, p. 11970 - 11978 (2009/02/05)
Catalytic ruthenium complexes in conjunction with an indium cocatalyst and Broensted acid isomerize primary and secondary propargylic alcohols in good yields to provide trans enals and enones exclusively. Readily available indenylbis(triphenylphosphine)ruthenium chloride, in the presence of indium triflate and camphorsulfonic acid, gives the best turnover numbers and reactivity with the broadest range of substrates. Deuterium labeling experiments suggest that the process occurs through propargylic hydride migration followed by protic cleavage of the resultant vinylruthenium intermediate. Application of this method to the synthesis of leukotriene B4 demonstrates its utility and extraordinary selectivity.
