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| D-LUCIFERIN Basic information |
| Product Name: | D-LUCIFERIN | | Synonyms: | 4,5-DIHYDRO-2-(6-HYDROXY-2-BENZOTHIAZOLYL)-4-THIAZOLECARBOXY;4,5-DIHYDRO-2-[6-HYDROXY-2-BENZOTHIAZOLYL]-4-THIAZOLE-CARBOXYLIC ACID;4,5-DIHYDRO-(6-HYDROXY-2-BENZOTHIAZOYL)-4-THIAZOLE CARBOXYLIC ACID;LUCIFERIN, D-;LUCIFERIN;D(-)-2-(6'-HYDROXY-BENZOTHIAZOLYL)-DELTA2-THIAZOLINE-4-CARBOXYLIC ACID;D(-)-LUCIFERIN;D-LUCIFERIN | | CAS: | 2591-17-5 | | MF: | C11H8N2O3S2 | | MW: | 280.32 | | EINECS: | 219-981-3 | | Product Categories: | Luciferines;substrate;Heterocycles;2591-17-5 | | Mol File: | 2591-17-5.mol |
| D-LUCIFERIN Chemical Properties |
| Melting point | 200-204 °C | | alpha | D22 -36° (c = 1.2 in DMF) | | Boiling point | 587.6±60.0 °C(Predicted) | | density | 1.4916 (rough estimate) | | refractive index | 1.5650 (estimate) | | storage temp. | -20°C | | form | Powder | | pka | 8.31±0.40(Predicted) | | color | Off-white to light yellow | | λmax | 360nm(H2O)(lit.) | | Merck | 14,4086 | | BRN | 30484 |
| D-LUCIFERIN Usage And Synthesis |
| Chemical Properties | off-white to light yellow powder | | Uses | In the assay of ATP. | | Uses | D-Luciferin has been used in determining luciferase activity by luciferase assay in mice and Arabidopsis thaliana seeds. It has also been used in measuring bioluminescence in neonatal rat ventricular cardiomyocytes. | | Uses | D-Luciferin has been used in the preparation of the reaction mixture for nitric oxide determination by minescence measurement. It has also been used in the preparation of D-luciferin stock solution for luciferin assays. | | Definition | ChEBI: A 1,3-thiazolemonocarboxylic acid consisting of 3,5-dihydrothiophene-4-carboxylic acid having a 6-hydroxybenzothiazol-2-yl group at the 2-position. | | General Description | D-Luciferin is a small molecule present abundantly in bioluminescent organisms. This molecule is sensitive to oxygen and light. | | Biochem/physiol Actions | D-Luciferin uptake within the cells is regulated by the adenosine triphosphate (ATP)-binding cassette (ABC) transporter inhibitors like ATP-binding cassette transporter G2 (ABCG2)/ breast cancer resistance protein (BCRP) inhibitor fumitremorgin C. This substrate is oxidized by firefly luciferase that results in emitting a photon, which has the capability of passing through living tissues. | | Purification Methods | D-Luciferin crystallises as pale yellow needles from H2O, or MeOH (83mg/7mL). It has UV max at 263 and 327nm (log 3.88 and 4.27) in 95% EtOH. The Na salt has a solubility of 4mg in 1 mL of 0.05M glycine. [White et al. J Am Chem Soc 83 2402 1961, 85 337 1963, UV and IR: Bitler & McElroy Arch Biochem 72 358 1957, Review: Cormier et al. Fortschr Chem Org Naturst 30 1 1973, Beilstein 27 III/IV 8934.] |
| D-LUCIFERIN Preparation Products And Raw materials |
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