Leukotriene B4

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 599290

CAS#: 71160-24-2

Description: Leukotriene B4 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.4 At higher concentrations, (1.0 x 10−7 M), LTB4 leads to neutrophil aggregation and degranulation as well as superoxide anion production.

Chemical Structure

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Leukotriene B4
CAS# 71160-24-2
Instruction

Theoretical Analysis

MedKoo Cat#: 599290
Name: Leukotriene B4
CAS#: 71160-24-2
Chemical Formula: C20H32O4
Exact Mass: 336.23
Molecular Weight: 336.470
Elemental Analysis: C, 71.39; H, 9.59; O, 19.02

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Leukotriene B4; LTB4; 5,12-Hete; 5,12-Dihete;

IUPAC/Chemical Name: (5R,6E,8E,10Z,12S,14Z)-5,12-dihydroxyicosa-6,8,10,14-tetraenoic acid

InChi Key: VNYSSYRCGWBHLG-DPBIBIDBSA-N

InChi Code: InChI=1S/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-/m0/s1

SMILES Code: CCCCC/C=C\C[C@H](O)/C=C\C=C\C=C\[C@H](O)CCCC(O)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 336.47 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Winslow V, Vaivoda R, Vasilyev A, Dombkowski D, Douaidy K, Stark C, Drake J, Guilliams E, Choudhary D, Preffer F, Stoilov I, Christmas P. Altered leukotriene B4 metabolism in CYP4F18-deficient mice does not impact inflammation following renal ischemia. Biochim Biophys Acta. 2014 Jun;1841(6):868-79. doi: 10.1016/j.bbalip.2014.03.002. Epub 2014 Mar 14. PubMed PMID: 24632148; PubMed Central PMCID: PMC4013684.

2: Lv J, Zou L, Zhao L, Yang W, Xiong Y, Li B, He R. Leukotriene B₄-leukotriene B₄ receptor axis promotes oxazolone-induced contact dermatitis by directing skin homing of neutrophils and CD8⁺ T cells. Immunology. 2015 Sep;146(1):50-8. doi: 10.1111/imm.12478. Epub 2015 Jun 29. PubMed PMID: 25959240; PubMed Central PMCID: PMC4552500.

3: Yokomizo T. Two distinct leukotriene B4 receptors, BLT1 and BLT2. J Biochem. 2015 Feb;157(2):65-71. doi: 10.1093/jb/mvu078. Epub 2014 Dec 4. PubMed PMID: 25480980.

4: Di Gennaro A, Haeggström JZ. Targeting leukotriene B4 in inflammation. Expert Opin Ther Targets. 2014 Jan;18(1):79-93. doi: 10.1517/14728222.2013.843671. Epub 2013 Oct 4. PubMed PMID: 24090264.

5: Andoh T, Takayama Y, Kuraishi Y. Involvement of leukotriene B4 in dermatophyte-related itch in mice. Pharmacol Rep. 2014 Aug;66(4):699-703. doi: 10.1016/j.pharep.2014.01.003. Epub 2014 Apr 26. PubMed PMID: 24948074.

6: Paschke F, Rabong C, Schuster C. Red light as a 12-oxo-leukotriene B₄ antagonist: an explanation for the efficacy of intensive red light in the therapy of peripheral inflammatory diseases. Biomed Tech (Berl). 2014 Dec;59(6):487-93. doi: 10.1515/bmt-2014-0014. PubMed PMID: 25029080.

7: Tian W, Jiang X, Tamosiuniene R, Sung YK, Qian J, Dhillon G, Gera L, Farkas L, Rabinovitch M, Zamanian RT, Inayathullah M, Fridlib M, Rajadas J, Peters-Golden M, Voelkel NF, Nicolls MR. Blocking macrophage leukotriene b4 prevents endothelial injury and reverses pulmonary hypertension. Sci Transl Med. 2013 Aug 28;5(200):200ra117. doi: 10.1126/scitranslmed.3006674. PubMed PMID: 23986401; PubMed Central PMCID: PMC4016764.

8: Primdahl KG, Tungen JE, Aursnes M, Hansen TV, Vik A. An efficient total synthesis of leukotriene B4. Org Biomol Chem. 2015 May 21;13(19):5412-7. doi: 10.1039/c5ob00473j. PubMed PMID: 25857248.

9: Waki H, Hendy EB, Hindmarch CC, Gouraud S, Toward M, Kasparov S, Murphy D, Paton JF. Excessive leukotriene B4 in nucleus tractus solitarii is prohypertensive in spontaneously hypertensive rats. Hypertension. 2013 Jan;61(1):194-201. doi: 10.1161/HYPERTENSIONAHA.112.192252. Epub 2012 Nov 19. PubMed PMID: 23172924; PubMed Central PMCID: PMC4506640.

10: Hirata K, Wada K, Murata Y, Nakajima A, Yamashiro T, Kamisaki Y. Critical role of leukotriene B4 receptor signaling in mouse 3T3-L1 preadipocyte differentiation. Lipids Health Dis. 2013 Aug 9;12:122. doi: 10.1186/1476-511X-12-122. PubMed PMID: 23937951; PubMed Central PMCID: PMC3751075.

11: Landa P, Kutil Z, Temml V, Malik J, Kokoska L, Widowitz U, Pribylova M, Dvorakova M, Marsik P, Schuster D, Bauer R, Vanek T. Inhibition of in vitro leukotriene B4 biosynthesis in human neutrophil granulocytes and docking studies of natural quinones. Nat Prod Commun. 2013 Jan;8(1):105-8. PubMed PMID: 23472470.

12: Lin W, Huang MQ, Xue X, Bertelsen K, Chen G, Zhao H, Lin ZJ, Fourie A, de Jong J, Weng N. A highly sensitive and selective method for the determination of leukotriene B4 (LTB4) in ex vivo stimulated human plasma by ultra fast liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Apr 15;925:54-62. doi: 10.1016/j.jchromb.2013.02.038. Epub 2013 Mar 8. PubMed PMID: 23523878.

13: Vigna SR, Shahid RA, Nathan JD, McVey DC, Liddle RA. Leukotriene B4 mediates inflammation via TRPV1 in duct obstruction-induced pancreatitis in rats. Pancreas. 2011 Jul;40(5):708-14. doi: 10.1097/MPA.0b013e318214c8df. PubMed PMID: 21602738; PubMed Central PMCID: PMC3116062.

14: McGee JE, Fitzpatrick FA. Erythrocyte-neutrophil interactions: formation of leukotriene B4 by transcellular biosynthesis. Proc Natl Acad Sci U S A. 1986 Mar;83(5):1349-53. PubMed PMID: 3006048; PubMed Central PMCID: PMC323073.

15: Serezani CH, Kane S, Collins L, Morato-Marques M, Osterholzer JJ, Peters-Golden M. Macrophage dectin-1 expression is controlled by leukotriene B4 via a GM-CSF/PU.1 axis. J Immunol. 2012 Jul 15;189(2):906-15. doi: 10.4049/jimmunol.1200257. Epub 2012 Jun 13. PubMed PMID: 22696442; PubMed Central PMCID: PMC3392366.

16: Lawson C, Bunting S, Holzgrefe H, Fitzpatrick F. Leukotriene B4 and 20-hydroxyleukotriene B4 contract guinea-pig trachea strips in vitro. J Pharmacol Exp Ther. 1986 Jun;237(3):888-92. PubMed PMID: 3012074.

17: Eun JC, Moore EE, Banerjee A, Kelher MR, Khan SY, Elzi DJ, McLaughlin NJ, Silliman CC. Leukotriene b4 and its metabolites prime the neutrophil oxidase and induce proinflammatory activation of human pulmonary microvascular endothelial cells. Shock. 2011 Mar;35(3):240-4. doi: 10.1097/SHK.0b013e3181faceb3. PubMed PMID: 20926984; PubMed Central PMCID: PMC3056395.

18: Yokomizo T. Leukotriene B4 receptors: novel roles in immunological regulations. Adv Enzyme Regul. 2011;51(1):59-64. doi: 10.1016/j.advenzreg.2010.08.002. Epub 2010 Oct 28. Review. PubMed PMID: 21035496.

19: Mita H, Turikisawa N, Yamada T, Taniguchi M. Quantification of leukotriene B4 glucuronide in human urine. Prostaglandins Other Lipid Mediat. 2007 Feb;83(1-2):42-9. Epub 2006 Dec 5. PubMed PMID: 17259071.

20: Hagmann W, Korte M. Hepatic uptake and metabolic disposition of leukotriene B4 in rats. Biochem J. 1990 Apr 15;267(2):467-70. PubMed PMID: 2159284; PubMed Central PMCID: PMC1131312.