Firefly luciferin

Base Information

• Chemical Name: Firefly luciferin
• CAS No.: 2591-17-5
• Molecular Formula: C11H8N2O3S2
• Molecular Weight: 280.328
• Hs Code.: 29342000
• European Community (EC) Number: 219-981-3
• UNII: 5TBB02N29K
• DSSTox Substance ID: DTXSID00894865
• Nikkaji Number: J7.623F
• Wikipedia: Firefly_luciferin
• Wikidata: Q3265801,Q63390514
• Metabolomics Workbench ID: 50803
• ChEMBL ID: CHEMBL443738
• Mol file: 2591-17-5.mol

Synonyms:D-luciferin

Chemical Property of Firefly luciferin

Chemical Property:

• Appearance/Colour: off-white to light yellow powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 200-204 °C
• Refractive Index: 1.865
• Boiling Point: 587.579 °C at 760 mmHg
• PKA: 8.31±0.40(Predicted)
• Flash Point: 309.157 °C
• PSA: 136.32000
• Density: 1.815 g/cm³
• LogP: 1.38410
• Storage Temp.: −20°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 279.99763447
• Heavy Atom Count: 18
• Complexity: 391

Purity/Quality:

98%, ^*data from raw suppliers

D-(-)-Luciferin [Chemiluminescence Reagent] >98.0%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Canonical SMILES: C1C(N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)O
• Isomeric SMILES: C1[C@@H](N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)O
• Uses: In the assay of ATP. 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. 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.

Technology Process of Firefly luciferin

There total 43 articles about Firefly luciferin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

D-cysteine (921-01-7) + 2-cyano-6-hydroxybenzothiazole (939-69-5) → D-luciferin (2591-17-5)

Guidance literature:

In water; at 20 ℃;

DOI:10.1055/s-0029-1217971

Reference yield: 86.0%

l-cysteine hydrochloride (52-89-1) + 2-cyano-6-hydroxybenzothiazole (939-69-5) → D-luciferin (2591-17-5)

Guidance literature:

l-cysteine hydrochloride; 2-cyano-6-hydroxybenzothiazole; In methanol; water; at 20 ℃; for 0.0833333h; Inert atmosphere;

With potassium carbonate; In methanol; water; at 20 ℃; for 0.333333h; Inert atmosphere;

Reference yield: 86.0%

D-cysteine hydrochloride (32443-99-5) + 2-cyano-6-hydroxybenzothiazole (939-69-5) → D-luciferin (2591-17-5)

Guidance literature:

With potassium carbonate; In methanol; water; for 0.333333h; Inert atmosphere;

DOI:10.1021/ja301493d

upstream raw materials:

S,S-cystine

2-cyano-6-hydroxybenzothiazole

D-cysteine hydrochloride

luciferin 2-nitro-5-methylbenzenesulfonate

Downstream raw materials:

2-(6’-hydroxy-2'-benzothiazolyl)-thiazole-4-carboxylic acid

2-(6-hydroxy-1,3-benzothiazol-2-yl)-1,3-thiazol-4(5H)-one

5'-adenosine monophosphate

Refernces

• 1、 Bazhin, Arkadiy A.,Sinisi, Riccardo,De Marchi, Umberto,Hermant, Aurélie,Sambiagio, Nicolas,Maric, Tamara,Budin, Ghyslain,Goun, Elena A.. "A bioluminescent probe for longitudinal monitoring of mitochondrial membrane potential". . p. 1385 - 1393. Retrieved 2020.
• 2、 Hemmi, Mayu,Ikeda, Yuma,Shindo, Yutaka,Nakajima, Takahiro,Nishiyama, Shigeru,Oka, Kotaro,Sato, Moritoshi,Hiruta, Yuki,Citterio, Daniel,Suzuki, Koji. "Highly Sensitive Bioluminescent Probe for Thiol Detection in Living Cells". . p. 648 - 655. Retrieved 2018.
• 3、 Feng, Ping,Zhang, Huateng,Deng, Quankun,Liu, Wei,Yang, Linghui,Li, Guobo,Chen, Guo,Du, Lupei,Ke, Bowen,Li, Minyong. "Real-Time Bioluminescence Imaging of Nitroreductase in Mouse Model". . p. 5610 - 5614. Retrieved 2016.
• 4、 Karatas, Hacer,Maric, Tamara,D'Alessandro, Pier Luca,Yevtodiyenko, Aleksey,Vorherr, Thomas,Hollingworth, Gregory J.,Goun, Elena A.. "Real-Time Imaging and Quantification of Peptide Uptake in Vitro and in Vivo". . p. 2197 - 2205. Retrieved 2019.
• 5、 Chen, Peiyao,Zheng, Zhen,Zhu, Yunxia,Dong, Yu,Wang, Fuqiang,Liang, Gaolin. "Bioluminescent Turn-On Probe for Sensing Hypochlorite in Vitro and in Tumors". . p. 5693 - 5696. Retrieved 2017.
• 6、 Jathoul, Amit P.,Grounds, Helen,Anderson, James C.,Pule, Martin A.. "A dual-color far-red to near-infrared firefly luciferin analogue designed for multiparametric bioluminescence imaging". . p. 13059 - 13063. Retrieved 2014.
• 7、 Ke, Bowen,Ma, Lin,Kang, Ting,He, Wei,Gou, Xueyan,Gong, Deying,Du, Lupei,Li, Minyong. "In Vivo Bioluminescence Imaging of Cobalt Accumulation in a Mouse Model". . p. 4946 - 4950. Retrieved 2018.
• 8、 ?wierczyńska, Ma?gorzata,Grzelakowska, Aleksandra,Modrzejewska, Julia,Podsiad?y, Rados?aw,S?owiński, Daniel,Siarkiewicz, Przemys?aw,Szala, Marcin,Zielonka, Jacek. "Characterization of the reactivity of luciferin boronate - A probe for inflammatory oxidants with improved stability". . . Retrieved 2020/08/12.