D-Luciferin sodium salt - ≥98% , CAS No.103404-75-7

CAS: 103404-75-7 Cat. No.: D115509 Molecular Weight: 302.3 EC Number: 600-430-4

GRADE & PURITY ≥98%

Synonyms

D-Luciferin Sodium | Sodium (S)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4,5-dihydrothiazole-4-carboxylate | C11H7N2NaO3S2 | D-Luciferin (sodium) | D-Luciferin sodium salt | D-(-)-Luciferin sodium | Firefly luciferin sodium | Beetle Luciferin sodium

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

D-Luciferin is mainly produced in bioluminescent organisms. It can simply circulate across the blood testis barrier, blood brain barrier and the blood placenta barrier. This small molecule is sensitive to light and oxygen. D-Luciferin is also sensitive to moisture in its powder form.

Application

D-Luciferin sodium salt has been used as a substrate in luciferin−luciferase chemiluminescence assay to determine ATP levels.
Substrate for firefly luciferase with a Km of approx 2 μM.

Specifications

Synonyms

D-Luciferin Sodium | Sodium (S)-2-(6-hydroxybenzo[d]thiazol-2-yl)-4, 5-dihydrothiazole-4-carboxylate | C11H7N2NaO3S2 | D-Luciferin (sodium) | D-Luciferin sodium salt | D-(-)-Luciferin sodium | Firefly luciferin sodium | Beetle Luciferin sodium

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Chemiluminescent luciferase substrate. Water soluble derivative of D-Luciferin and analog of D-Luciferin potassium salt. Excitation is pH dependent (pH ex λ = 327 and 385 nm for pH 4 and pH 11 respectively)

Storage

Protected from light, Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488192435
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488192435
• Canonical Smiles: C1C(N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)[O-].[Na+]
• IUPAC Name: sodium;(4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylate
• InChIKey: LILQLBIQROYWIA-OGFXRTJISA-M
• INCHI: 1S/C11H8N2O3S2.Na/c14-5-1-2-6-8(3-5)18-10(12-6)9-13-7(4-17-9)11(15)16;/h1-3,7,14H,4H2,(H,15,16);/q;+1/p-1/t7-;/m1./s1
• Isomeric SMILES: C1[C@@H](N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)[O-].[Na+]
• WGK Germany: 3
• Molecular Weight: 302.3
• Reaxy-Rn: 62728073
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=62728073&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Amino acids and derivatives
          • Level6 Alpha amino acids and derivatives
            • Level7 Cysteine and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Amino acids and derivatives - Alpha amino acids and derivatives
• Direct Parent: Cysteine and derivatives
• Alternative Parents: Benzothiazoles 1-hydroxy-2-unsubstituted benzenoids Imidothiolactones Thiazolines Thiazoles Heteroaromatic compounds Carboxylic acid salts Sulfenyl compounds Propargyl-type 1,3-dipolar organic compounds Organic alkali metal salts Monocarboxylic acids and derivatives Imidothioic acids and derivatives Azacyclic compounds Organopnictogen compounds Organooxygen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Cysteine or derivatives - 1,3-benzothiazole - 1-hydroxy-2-unsubstituted benzenoid - Imidothiolactone - Benzenoid - Heteroaromatic compound - Meta-thiazoline - Thiazole - Azole - Imidothioester - Carboxylic acid salt - Azacycle - Organic alkali metal salt - Organic metal salt - Organoheterocyclic compound - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Sulfenyl compound - Monocarboxylic acid or derivatives - Imidothioic acid or derivatives - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organic salt - Organosulfur compound - Organooxygen compound - Organonitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as cysteine and derivatives. These are compounds containing cysteine or a derivative thereof resulting from reaction of cysteine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in water (10 mg/ml), ethanol (~0.25 mg/ml), DMSO (~10 mg/ml), DMF (~16.7 mg/ml), and PBS pH 7.2 (~10 mg/ml).
• Sensitivity: light & Moisture sensitive
• Molecular Weight: 302.300 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 301.98 Da
• Monoisotopic Mass: 301.98 Da
• Topological Polar Surface Area: 139.000 Ų
• Heavy Atom Count: 19
• Formal Charge: 0
• Complexity: 396.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

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