Lumirubin | CAS#83664-21-5 | photoproduct

MedKoo Cat#: 584571 | Name: Lumirubin

Description:

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

Lumirubin is a water-soluble photoproduct of bilirubin formed in vivo during phototherapy.

Chemical Structure

Lumirubin

CAS#83664-21-5

Theoretical Analysis

MedKoo Cat#: 584571

Name: Lumirubin

CAS#: 83664-21-5

Chemical Formula: C33H36N4O6

Exact Mass: 584.2635

Molecular Weight: 584.67

Elemental Analysis: C, 67.79; H, 6.21; N, 9.58; O, 16.42

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 #

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Synonym

Lumirubin; (E,Z)-Bilirubin IXα; (E,Z)-Cyclobilirubin; (E,Z)-Cyclobilirubin IXα; (EZ)-Cyclobilirubin; (EZ)-Cyclobilirubin IXα; Lumirubin IX;

IUPAC/Chemical Name

1H-Cyclohepta(2,1-b:4,5-b')dipyrrole-6-propanoic acid, 7-((3-(2-carboxyethyl)-5-((4-ethenyl-1,5-dihydro-3-methyl-5-oxo-2H-pyrrol-2-ylidene)methyl)-4-methyl-1H-pyrrol-2-yl)methyl)-2,3,5,5a-tetrahydro-3,5a-dimethyl-2-oxo-

InChi Key

BYVDUQYJIIPFIB-CFRMEGHHSA-N

InChi Code

InChI=1S/C33H36N4O6/c1-6-19-16(2)24(36-32(19)43)13-23-17(3)20(7-9-29(38)39)25(34-23)14-27-22(8-10-30(40)41)33(5)12-11-21-18(4)31(42)37-26(21)15-28(33)35-27/h6,11,13,15,18,34H,1,7-10,12,14H2,2-5H3,(H,36,43)(H,37,42)(H,38,39)(H,40,41)/b24-13-

SMILES Code

O=C(O)CCC1=C(CC2=C(CCC(O)=O)C(C)=C(/C=C(C(C)=C3C=C)\NC3=O)N2)N=C4C1(C)CC=C(C5C)C(NC5=O)=C4

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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 584.67 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.

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: Jasprova J, Dal Ben M, Vianello E, Goncharova I, Urbanova M, Vyroubalova K, Gazzin S, Tiribelli C, Sticha M, Cerna M, Vitek L. The Biological Effects of Bilirubin Photoisomers. PLoS One. 2016 Feb 1;11(2):e0148126. doi: 10.1371/journal.pone.0148126. eCollection 2016. PubMed PMID: 26829016; PubMed Central PMCID: PMC4735493. 2: Knox I, Ennever JF, Speck WT. Urinary excretion of an isomer of bilirubin during phototherapy. Pediatr Res. 1985 Feb;19(2):198-201. PubMed PMID: 3982878. 3: Goncharova I, Jašprová J, Vítek L, Urbanová M. Photo-isomerization and oxidation of bilirubin in mammals is dependent on albumin binding. Anal Biochem. 2015 Dec 1;490:34-45. doi: 10.1016/j.ab.2015.08.001. Epub 2015 Aug 19. PubMed PMID: 26297581. 4: Costarino AT Jr, Ennever JF, Baumgart S, Speck WT, Polin RA. Effect of spectral distribution on isomerization of bilirubin in vivo. J Pediatr. 1985 Jul;107(1):125-8. PubMed PMID: 4009328. 5: Agati G, Fusi F, Donzelli GP, Pratesi R. Quantum yield and skin filtering effects on the formation rate of lumirubin. J Photochem Photobiol B. 1993 May;18(2-3):197-203. PubMed PMID: 8350187. 6: Ebbesen F, Madsen PH, Vandborg PK, Jakobsen LH, Trydal T, Vreman HJ. Bilirubin isomer distribution in jaundiced neonates during phototherapy with LED light centered at 497 nm (turquoise) vs. 459 nm (blue). Pediatr Res. 2016 Oct;80(4):511-5. doi: 10.1038/pr.2016.115. Epub 2016 May 25. PubMed PMID: 27331354. 7: Malhotra V, Greenberg JW, Dunn LL, Ennever JF. Fatty acid enhancement of the quantum yield for the formation of lumirubin from bilirubin bound to human albumin. Pediatr Res. 1987 Jun;21(6):530-3. PubMed PMID: 3601472. 8: Bacci M, Linari R, Agati G, Fusi F. UV excitable fluorescence of lumirubin. J Photochem Photobiol B. 1989 Jun;3(3):419-27. PubMed PMID: 2504903. 9: Migliorini MG, Galvan P, Sbrana G, Donzelli GP, Vecchi C. Bilirubin photoconversion induced by monochromatic laser radiation. Comparison between aerobic and anaerobic experiments in vitro. Biochem J. 1988 Dec 15;256(3):841-6. PubMed PMID: 3223957; PubMed Central PMCID: PMC1135492. 10: Ennever JF, Costarino AT, Polin RA, Speck WT. Rapid clearance of a structural isomer of bilirubin during phototherapy. J Clin Invest. 1987 Jun;79(6):1674-8. PubMed PMID: 3584465; PubMed Central PMCID: PMC424499. 11: McDonagh AF, Agati G, Fusi F, Pratesi R. Quantum yields for laser photocyclization of bilirubin in the presence of human serum albumin. Dependence of quantum yield on excitation wavelength. Photochem Photobiol. 1989 Sep;50(3):305-19. PubMed PMID: 2780821. 12: Myara A, Sender A, Valette V, Rostoker C, Paumier D, Capoulade C, Loridon F, Bouillie J, Milliez J, Brossard Y, Trivin F. Early changes in cutaneous bilirubin and serum bilirubin isomers during intensive phototherapy of jaundiced neonates with blue and green light. Biol Neonate. 1997;71(2):75-82. PubMed PMID: 9057990. 13: Pratesi R, Agati G, Fusi F. Phototherapy for neonatal hyperbilirubinemia. Photodermatol. 1989 Dec;6(6):244-57. Review. PubMed PMID: 2700092. 14: Costarino AT, Ennever JF, Baumgart S, Speck WT, Paul M, Polin RA. Bilirubin photoisomerization in premature neonates under low- and high-dose phototherapy. Pediatrics. 1985 Mar;75(3):519-22. PubMed PMID: 3975120. 15: Ennever JF, Dresing TJ. Quantum yields for the cyclization and configurational isomerization of 4E,15Z-bilirubin. Photochem Photobiol. 1991 Jan;53(1):25-32. PubMed PMID: 2027905. 16: Moan J. [Light therapy of newborns with hyperbilirubinemia]. Tidsskr Nor Laegeforen. 1992 Apr 30;112(11):1459-63. Review. Norwegian. PubMed PMID: 1631823. 17: Dicken P, Grant LJ, Jones S. An evaluation of the characteristics and performance of neonatal phototherapy equipment. Physiol Meas. 2000 Nov;21(4):493-503. PubMed PMID: 11110247. 18: Ennever JF, Knox I, Denne SC, Speck WT. Phototherapy for neonatal jaundice: in vivo clearance of bilirubin photoproducts. Pediatr Res. 1985 Feb;19(2):205-8. PubMed PMID: 3982880. 19: Agati G, Fusi F, Pratesi S, Galvan P, Donzelli GP. Bilirubin photoisomerization products in serum and urine from a Crigler-Najjar type I patient treated by phototherapy. J Photochem Photobiol B. 1998 Dec;47(2-3):181-9. PubMed PMID: 10093917. 20: McDonagh AF. Light effects on transport and excretion of bilirubin in newborns. Ann N Y Acad Sci. 1985;453:65-72. PubMed PMID: 3865597.