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MedKoo Cat#: 528092 | Name: Lipoxin B4

Description:

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

Lipoxin B4 is an anti-inflammatory agent.

Chemical Structure

Lipoxin B4
CAS#92950-25-9

Theoretical Analysis

MedKoo Cat#: 528092

Name: Lipoxin B4

CAS#: 92950-25-9

Chemical Formula: C20H32O5

Exact Mass: 352.2250

Molecular Weight: 352.47

Elemental Analysis: C, 68.15; H, 9.15; O, 22.70

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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Related CAS #
No Data
Synonym
Lipoxin B4
IUPAC/Chemical Name
5,14,15-Trihydroxy-6,8,10,12-eicosatetraenoic acid
InChi Key
UXVRTOKOJOMENI-ICTGYCPSSA-N
InChi Code
InChI=1S/C20H32O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h4-7,9-10,12,15,17-19,21-23H,2-3,8,11,13-14,16H2,1H3,(H,24,25)/b6-4+,7-5+,12-9+,15-10+
SMILES Code
CCCCCC(O)C(O)/C=C/C=C/C=C/C=C/C(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 352.47 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: Kim N, Lannan KL, Thatcher TH, Pollock SJ, Woeller CF, Phipps RP. Lipoxin B(4) Enhances Human Memory B Cell Antibody Production via Upregulating Cyclooxygenase-2 Expression. J Immunol. 2018 Oct 22. pii: ji1700503. doi: 10.4049/jimmunol.1700503. [Epub ahead of print] PubMed PMID: 30348736. 2: Okada K, Hosooka T, Shinohara M, Ogawa W. Modulation of lipid mediator profile may contribute to amelioration of chronic inflammation in adipose tissue of obese mice by pioglitazone. Biochem Biophys Res Commun. 2018 Oct 20;505(1):29-35. doi: 10.1016/j.bbrc.2018.09.081. Epub 2018 Sep 17. PubMed PMID: 30236987. 3: Norris PC, Serhan CN. Metabololipidomic profiling of functional immunoresolvent clusters and eicosanoids in mammalian tissues. Biochem Biophys Res Commun. 2018 Oct 7;504(3):553-561. doi: 10.1016/j.bbrc.2018.03.037. Epub 2018 Mar 15. PubMed PMID: 29524409; PubMed Central PMCID: PMC6139088. 4: Navratil AR, Shchepinov MS, Dennis EA. Lipidomics Reveals Dramatic Physiological Kinetic Isotope Effects during the Enzymatic Oxygenation of Polyunsaturated Fatty Acids Ex Vivo. J Am Chem Soc. 2018 Jan 10;140(1):235-243. doi: 10.1021/jacs.7b09493. Epub 2017 Dec 19. PubMed PMID: 29206462; PubMed Central PMCID: PMC5765537. 5: Norris PC, Libreros S, Chiang N, Serhan CN. A cluster of immunoresolvents links coagulation to innate host defense in human blood. Sci Signal. 2017 Aug 1;10(490). pii: eaan1471. doi: 10.1126/scisignal.aan1471. PubMed PMID: 28765512; PubMed Central PMCID: PMC5683850. 6: Prevete N, Liotti F, Illiano A, Amoresano A, Pucci P, de Paulis A, Melillo RM. Formyl peptide receptor 1 suppresses gastric cancer angiogenesis and growth by exploiting inflammation resolution pathways. Oncoimmunology. 2017 Feb 21;6(4):e1293213. doi: 10.1080/2162402X.2017.1293213. eCollection 2017. PubMed PMID: 28507800; PubMed Central PMCID: PMC5414878. 7: Lee S, Nakahira K, Dalli J, Siempos II, Norris PC, Colas RA, Moon JS, Shinohara M, Hisata S, Howrylak JA, Suh GY, Ryter SW, Serhan CN, Choi AMK. NLRP3 Inflammasome Deficiency Protects against Microbial Sepsis via Increased Lipoxin B(4) Synthesis. Am J Respir Crit Care Med. 2017 Sep 15;196(6):713-726. doi: 10.1164/rccm.201604-0892OC. PubMed PMID: 28245134; PubMed Central PMCID: PMC5620673. 8: Elajami TK, Colas RA, Dalli J, Chiang N, Serhan CN, Welty FK. Specialized proresolving lipid mediators in patients with coronary artery disease and their potential for clot remodeling. FASEB J. 2016 Aug;30(8):2792-801. doi: 10.1096/fj.201500155R. Epub 2016 Apr 27. PubMed PMID: 27121596; PubMed Central PMCID: PMC4970606. 9: Karra L, Haworth O, Priluck R, Levy BD, Levi-Schaffer F. Lipoxin B₄ promotes the resolution of allergic inflammation in the upper and lower airways of mice. Mucosal Immunol. 2015 Jul;8(4):852-62. doi: 10.1038/mi.2014.116. Epub 2014 Dec 3. PubMed PMID: 25465102; PubMed Central PMCID: PMC4454640. 10: Homann J, Lehmann C, Kahnt AS, Steinhilber D, Parnham MJ, Geisslinger G, Ferreirós N. Chiral chromatography-tandem mass spectrometry applied to the determination of pro-resolving lipid mediators. J Chromatogr A. 2014 Sep 19;1360:150-63. doi: 10.1016/j.chroma.2014.07.068. Epub 2014 Jul 29. PubMed PMID: 25124229. 11: Le Faouder P, Baillif V, Spreadbury I, Motta JP, Rousset P, Chêne G, Guigné C, Tercé F, Vanner S, Vergnolle N, Bertrand-Michel J, Dubourdeau M, Cenac N. LC-MS/MS method for rapid and concomitant quantification of pro-inflammatory and pro-resolving polyunsaturated fatty acid metabolites. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 Aug 1;932:123-33. doi: 10.1016/j.jchromb.2013.06.014. Epub 2013 Jun 15. PubMed PMID: 23831705. 12: Hu S, Mao-Ying QL, Wang J, Wang ZF, Mi WL, Wang XW, Jiang JW, Huang YL, Wu GC, Wang YQ. Lipoxins and aspirin-triggered lipoxin alleviate bone cancer pain in association with suppressing expression of spinal proinflammatory cytokines. J Neuroinflammation. 2012 Dec 26;9:278. doi: 10.1186/1742-2094-9-278. PubMed PMID: 23268791; PubMed Central PMCID: PMC3558391. 13: O'Sullivan TP, Vallin KS, Shah ST, Fakhry J, Maderna P, Scannell M, Sampaio AL, Perretti M, Godson C, Guiry PJ. Aromatic lipoxin A4 and lipoxin B4 analogues display potent biological activities. J Med Chem. 2007 Nov 29;50(24):5894-902. Epub 2007 Oct 26. PubMed PMID: 17960922. 14: Parkinson JF. Lipoxin and synthetic lipoxin analogs: an overview of anti-inflammatory functions and new concepts in immunomodulation. Inflamm Allergy Drug Targets. 2006 Apr;5(2):91-106. Review. PubMed PMID: 16613568. 15: Tokheim AM, Martin BL. Inhibition of calcineurin by polyunsaturated lipids. Bioorg Chem. 2006 Apr;34(2):66-76. Epub 2006 Feb 7. PubMed PMID: 16464485. 16: Serhan CN. Lipoxins and aspirin-triggered 15-epi-lipoxins are the first lipid mediators of endogenous anti-inflammation and resolution. Prostaglandins Leukot Essent Fatty Acids. 2005 Sep-Oct;73(3-4):141-62. Review. PubMed PMID: 16005201. 17: Ariel A, Chiang N, Arita M, Petasis NA, Serhan CN. Aspirin-triggered lipoxin A4 and B4 analogs block extracellular signal-regulated kinase-dependent TNF-alpha secretion from human T cells. J Immunol. 2003 Jun 15;170(12):6266-72. PubMed PMID: 12794159. 18: Goh J, Godson C, Brady HR, Macmathuna P. Lipoxins: pro-resolution lipid mediators in intestinal inflammation. Gastroenterology. 2003 Apr;124(4):1043-54. Review. PubMed PMID: 12671901. 19: Stenson C, Mitchell S, Lappin D, Brady HR, Godson C. Biphasic regulation of leukocyte trafficking by lipoxins. Adv Exp Med Biol. 2002;507:543-9. Review. PubMed PMID: 12664638. 20: Bonnans C, Vachier I, Chavis C, Godard P, Bousquet J, Chanez P. Lipoxins are potential endogenous antiinflammatory mediators in asthma. Am J Respir Crit Care Med. 2002 Jun 1;165(11):1531-5. PubMed PMID: 12045128.

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