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MedKoo Cat#: 527972 | Name: Lumichrome
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Description:

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

Lumichrome (7,8-Dimethylalloxazine) is a natural metabolite of riboflavin. It is a flourescent photoproduct of riboflavin degradation.

Chemical Structure

Lumichrome
Lumichrome
CAS#1086-80-2

Theoretical Analysis

MedKoo Cat#: 527972

Name: Lumichrome

CAS#: 1086-80-2

Chemical Formula: C12H10N4O2

Exact Mass: 242.0804

Molecular Weight: 242.24

Elemental Analysis: C, 59.50; H, 4.16; N, 23.13; O, 13.21

Price and Availability

Size Price Availability Quantity
1g USD 450.00 2 Weeks
5g USD 1,050.00 2 Weeks
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Related CAS #
No Data
Synonym
7,8-Dimethylalloxazine
IUPAC/Chemical Name
Benzo(g)pteridine-2,4(1H,3H)-dione, 7,8-dimethyl-
InChi Key
ZJTJUVIJVLLGSP-UHFFFAOYSA-N
InChi Code
InChI=1S/C12H10N4O2/c1-5-3-7-8(4-6(5)2)14-10-9(13-7)11(17)16-12(18)15-10/h3-4H,1-2H3,(H2,14,15,16,17,18)
SMILES Code
O=C(N1)NC2=NC3=CC(C)=C(C)C=C3N=C2C1=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 242.24 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: Pholo M, Coetzee B, Maree HJ, Young PR, Lloyd JR, Kossmann J, Hills PN. Cell division and turgor mediate enhanced plant growth in Arabidopsis plants treated with the bacterial signalling molecule lumichrome. Planta. 2018 Aug;248(2):477-488. doi: 10.1007/s00425-018-2916-8. Epub 2018 May 17. PubMed PMID: 29777364. 2: Andrioli WJ, Lopes AA, Cavalcanti BC, Pessoa C, Nanayakkara NPD, Bastos JK. Isolation and characterization of 2-pyridone alkaloids and alloxazines from Beauveria bassiana. Nat Prod Res. 2017 Aug;31(16):1920-1929. doi: 10.1080/14786419.2016.1269091. Epub 2016 Dec 29. PubMed PMID: 28032511. 3: Jerković I, Marijanović Z, Zekić M, Tuberoso CI. First Report on Rare Unifloral Honey of Endemic Moltkia petraea (Tratt.) Griseb. from Croatia: Detailed Chemical Screening and Antioxidant Capacity. Chem Biodivers. 2017 Mar;14(3). doi: 10.1002/cbdv.201600268. Epub 2017 Feb 9. PubMed PMID: 27718325. 4: Maity B, Ahmed SA, Seth D. Interaction of Biologically Active Flavins inside Bile Salt Aggregates: Molecular Level Investigation. J Phys Chem B. 2016 Sep 22;120(37):9854-66. doi: 10.1021/acs.jpcb.6b04870. Epub 2016 Sep 8. PubMed PMID: 27557394. 5: Valerón Bergh VJ, Hjorth Tønnesen H. Interaction between the photosensitizer lumichrome and human serum albumin: effect of excipients. Pharm Dev Technol. 2017 Dec;22(8):992-1000. doi: 10.1080/10837450.2016.1212883. Epub 2016 Jul 27. PubMed PMID: 27465857. 6: Shi J, Feng SX, Wang JH, Xue L, Tian LP. [Chemical constituents of ethyl acetate fraction from seed melon (Citrulluslanatus ssp. vulgaris var. megalaspermus)]. Zhongguo Zhong Yao Za Zhi. 2016 Jul;41(13):2455-2459. doi: 10.4268/cjcmm20161314. Chinese. PubMed PMID: 28905568. 7: Bergh VJ, Bruzell E, Hegge AB, Tønnesen HH. Influence of formulation on photoinactivation of bacteria by lumichrome. Pharmazie. 2015 Sep;70(9):574-80. PubMed PMID: 26492641. 8: Yamamoto K, Asano Y. Efficient production of lumichrome by Microbacterium sp. strain TPU 3598. Appl Environ Microbiol. 2015 Nov;81(21):7360-7. doi: 10.1128/AEM.02166-15. Epub 2015 Aug 7. PubMed PMID: 26253661; PubMed Central PMCID: PMC4592859. 9: Ahmad I, Anwar Z, Ahmed S, Sheraz MA, Bano R, Hafeez A. Solvent Effect on the Photolysis of Riboflavin. AAPS PharmSciTech. 2015 Oct;16(5):1122-8. doi: 10.1208/s12249-015-0304-2. Epub 2015 Feb 21. PubMed PMID: 25698084; PubMed Central PMCID: PMC4674638. 10: Hong J, Lee M, Lee B, Seo DH, Park CB, Kang K. Biologically inspired pteridine redox centres for rechargeable batteries. Nat Commun. 2014 Oct 31;5:5335. doi: 10.1038/ncomms6335. PubMed PMID: 25359101. 11: Günther A, Nieto P, Berden G, Oomens J, Dopfer O. IRMPD spectroscopy of metalated flavins: structure and bonding of M(q+)-lumichrome complexes (M(q+) = Li⁺-Cs⁺, Ag⁺, Mg²⁺). Phys Chem Chem Phys. 2014 Jul 21;16(27):14161-71. doi: 10.1039/c4cp01524j. Epub 2014 Jun 6. PubMed PMID: 24905966. 12: Langer J, Günther A, Seidenbecher S, Berden G, Oomens J, Dopfer O. Probing protonation sites of isolated flavins using IR spectroscopy: from lumichrome to the cofactor flavin mononucleotide. Chemphyschem. 2014 Aug 25;15(12):2550-62. doi: 10.1002/cphc.201402146. Epub 2014 Jun 4. PubMed PMID: 24895155. 13: Sato Y, Kageyama T, Nishizawa S, Teramae N. Competitive binding of abasic site-binding ligands and masking ligands to DNA duplexes for the analysis of single-base mutation. Anal Sci. 2013;29(1):15-9. PubMed PMID: 23303078. 14: Tuberoso CI, Jerković I, Bifulco E, Marijanovic Z, Congiu F, Bubalo D. Riboflavin and lumichrome in Dalmatian sage honey and other unifloral honeys determined by LC-DAD technique. Food Chem. 2012 Dec 1;135(3):1985-90. doi: 10.1016/j.foodchem.2012.06.096. Epub 2012 Jul 4. PubMed PMID: 22953948. 15: Prukała D, Sikorska E, Koput J, Khmelinskii I, Karolczak J, Gierszewski M, Sikorski M. Acid-base equilibriums of lumichrome and its 1-methyl, 3-methyl, and 1,3-dimethyl derivatives. J Phys Chem A. 2012 Jul 19;116(28):7474-90. doi: 10.1021/jp300522h. Epub 2012 Jul 10. PubMed PMID: 22731984. 16: Patel M, Vadlapatla RK, Pal D, Mitra AK. Molecular and functional characterization of riboflavin specific transport system in rat brain capillary endothelial cells. Brain Res. 2012 Aug 15;1468:1-10. doi: 10.1016/j.brainres.2012.05.052. Epub 2012 Jun 7. PubMed PMID: 22683359; PubMed Central PMCID: PMC3405183. 17: Diakonis VF, Grentzelos MA, Tzatzarakis MN, Kankaria V, Karavitaki A, Karatapanis AE, Tsatsakis AM, Kymionis GD. Riboflavin's time-dependent degradation rate induced by ultraviolet A irradiation. Eur J Ophthalmol. 2012;22 Suppl 7:S51-6. doi: 10.5301/ejo.5000114. PubMed PMID: 22267456. 18: Remucal CK, McNeill K. Photosensitized amino acid degradation in the presence of riboflavin and its derivatives. Environ Sci Technol. 2011 Jun 15;45(12):5230-7. doi: 10.1021/es200411a. Epub 2011 May 18. PubMed PMID: 21591753. 19: Moyon NS, Mitra S. Fluorescence solvatochromism in lumichrome and excited-state tautomerization: a combined experimental and DFT study. J Phys Chem A. 2011 Mar 31;115(12):2456-64. doi: 10.1021/jp1102687. Epub 2011 Mar 9. PubMed PMID: 21388154. 20: Marchena M, Gil M, Martín C, Organero JA, Sanchez F, Douhal A. Stability and photodynamics of lumichrome structures in water at different pHs and in chemical and biological caging media. J Phys Chem B. 2011 Mar 17;115(10):2424-35. doi: 10.1021/jp110134f. Epub 2011 Feb 18. PubMed PMID: 21332111.