MedKoo Cat#: 599290 | Name: Leukotriene B4

Description:

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

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

Leukotriene B4
CAS#71160-24-2

Theoretical Analysis

MedKoo Cat#: 599290

Name: Leukotriene B4

CAS#: 71160-24-2

Chemical Formula: C20H32O4

Exact Mass: 336.2301

Molecular Weight: 336.47

Elemental Analysis: C, 71.39; H, 9.59; O, 19.02

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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

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
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.