D-Luciferin - 10mM in DMSO , CAS No.2591-17-5

CAS: 2591-17-5 Cat. No.: D422906 Molecular Weight: 280.32 Beilstein Registry Number: 27(4)8934 EC Number: 219-981-3
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GRADE & PURITY 10mM in DMSO
Synonyms
firefly luciferin (ketone tautomer) | L-8200 | 4-Thiazolecarboxylic acid, 4,5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-, (S)- | BDBM50440036 | D-Luciferin, synthetic | EN300-99574 | 5TBB02N29K | Firefly luciferin | UNII-5TBB02N29K | s7763 | 3''-propionylleu
Storage
Store at -80°C
Shipped In
Dry ice packs + Cold packs
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Size
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Price
Qty
1ml
D422906-1ml
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Why this grade

10mM in DMSO for sensitive chromatographic and analytical workflows requiring minimal baseline interference.

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Storage & shipping

Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.

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Quality documents

SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.

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Literature proof

Cited in 24 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.

Overview

D-luciferin is the natural substrate of luciferases that catalyze the production of light in bioluminescent insects.

Specifications

Synonyms
firefly luciferin (ketone tautomer) | L-8200 | 4-Thiazolecarboxylic acid, 4, 5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-, (S)- | BDBM50440036 | D-Luciferin, synthetic | EN300-99574 | 5TBB02N29K | Firefly luciferin | UNII-5TBB02N29K | s7763 | 3''-propionylleu
Specifications & Purity
10mM in DMSO
Biochemical and Physiological Mechanisms
Cell-permeable chemiluminescent luciferase substrate. Emits lights upon oxidative decarboxylation in the presence of ATP. Provides a bioluminescent signal for cellular ATP levels in vivo.
Storage
Store at -80°C
Shipped In
Dry ice packs + Cold packs
This product requires cold chain shipping. Ground and other economy services are not available.
Names and Identifiers
Canonical SmilesC1C(N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)O
IUPAC Name(4S)-2-(6-hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid
InChIKeyBJGNCJDXODQBOB-SSDOTTSWSA-N
INCHI1S/C11H8N2O3S2/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)/t7-/m1/s1
Isomeric SMILES C1[C@@H](N=C(S1)C2=NC3=C(S2)C=C(C=C3)O)C(=O)O
WGK Germany 3
Molecular Weight 280.32
Beilstein 27(4)8934
Reaxy-Rn 269810
Reaxys-RN_link_address https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=269810&ln=

Documentation

📋 Safety Data Sheet (SDS)

Comprehensive hazard, handling, storage, and regulatory compliance document.

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✅ Certificate of Analysis (COA)

Lot-specific quality data. Enter your lot number to retrieve the exact COA.

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📊 Datasheet

Quick-reference summary of product specifications and applications.

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🔬 Specification Sheet

Full quality attributes and acceptance criteria for this grade.

View spec sheet →

Advanced Data

Taxonomic Classification

Taxonomy Tree

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree Nodes Amino acids and derivatives
Direct ParentAlpha amino acids and derivatives
Alternative Parents Benzothiazoles  1-hydroxy-2-unsubstituted benzenoids  Imidothiolactones  Thiazolines  Thiazoles  Heteroaromatic compounds  Propargyl-type 1,3-dipolar organic compounds  Monocarboxylic acids and derivatives  Carboxylic acids  Azacyclic compounds  Organopnictogen compounds  Organonitrogen compounds  Organic oxides  Hydrocarbon derivatives  Carbonyl compounds  
Molecular FrameworkAromatic heteropolycyclic compounds
Substituents Alpha-amino acid or derivatives - 1,3-benzothiazole - 1-hydroxy-2-unsubstituted benzenoid - Benzenoid - Imidothiolactone - Azole - Thiazole - Meta-thiazoline - Heteroaromatic compound - Carboxylic acid - Monocarboxylic acid or derivatives - Azacycle - Propargyl-type 1,3-dipolar organic compound - Organic 1,3-dipolar compound - Organoheterocyclic compound - Organooxygen compound - Organonitrogen compound - Organic oxide - Hydrocarbon derivative - Organic oxygen compound - Organopnictogen compound - Carbonyl group - Organic nitrogen compound - Aromatic heteropolycyclic compound
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
External Descriptors benzothiazoles - 1,3-thiazolemonocarboxylic acid - imidothioate
3D Structure
Interactive Chemical Structure Model





Associated Targets(Human)
INSR Tclin Insulin receptor (5558 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IGF1R Tclin Insulin-like growth factor I receptor (8605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK11 Tchem MAP kinase p38 beta (2785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK14 Tchem MAP kinase p38 alpha (12866 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKCZ Tchem Protein kinase C zeta (2414 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MYLK Tchem Myosin light chain kinase, smooth muscle (1267 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
FGFR1 Tclin Fibroblast growth factor receptor 1 (9149 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
STK3 Tchem Serine/threonine-protein kinase MST2 (3069 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CSNK1D Tchem Casein kinase I delta (4546 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SRC Tclin Tyrosine-protein kinase SRC (10310 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHEK2 Tchem Serine/threonine-protein kinase Chk2 (4015 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PDPK1 Tchem 3-phosphoinositide dependent protein kinase-1 (3758 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AKT2 Tchem Serine/threonine-protein kinase AKT2 (4301 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IKBKB Tchem Inhibitor of nuclear factor kappa B kinase beta subunit (5554 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AURKB Tchem Serine/threonine-protein kinase Aurora-B (6805 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PIM1 Tchem Serine/threonine-protein kinase PIM1 (9629 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PKN2 Tchem Protein kinase N2 (1991 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CSK Tchem Tyrosine-protein kinase CSK (2395 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPS6KA5 Tchem Ribosomal protein S6 kinase alpha 5 (3355 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKD1 Tchem Protein kinase C mu (1904 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SYK Tclin Tyrosine-protein kinase SYK (7372 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPS6KA1 Tchem Ribosomal protein S6 kinase alpha 1 (2796 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
JAK2 Tclin Tyrosine-protein kinase JAK2 (12915 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CAMK1 Tchem CaM kinase I alpha (1664 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK13 Tchem MAP kinase p38 delta (2605 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPKAPK2 Tchem MAP kinase-activated protein kinase 2 (4814 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPKAPK5 Tchem MAP kinase-activated protein kinase 5 (2831 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ROCK2 Tclin Rho-associated protein kinase 2 (6206 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK9 Tchem c-Jun N-terminal kinase 2 (4655 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK10 Tchem c-Jun N-terminal kinase 3 (3396 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAP2K1 Tclin Dual specificity mitogen-activated protein kinase kinase 1 (4127 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
PRKCA Tchem Protein kinase C alpha (5923 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK3 Tchem MAP kinase ERK1 (4725 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAP3K11 Tchem Mitogen-activated protein kinase kinase kinase 11 (808 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
NTRK1 Tclin Nerve growth factor receptor Trk-A (7922 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAP3K9 Tchem Mitogen-activated protein kinase kinase kinase 9 (945 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
DYRK1A Tchem Dual-specificity tyrosine-phosphorylation regulated kinase 1A (6484 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAPK8 Tchem c-Jun N-terminal kinase 1 (5038 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
MAP3K1 Tchem Mitogen-activated protein kinase kinase kinase 1 (590 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
ERBB4 Tclin Receptor protein-tyrosine kinase erbB-4 (2748 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
SGK1 Tchem Serine/threonine-protein kinase Sgk1 (2343 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPS6KA3 Tchem Ribosomal protein S6 kinase alpha 3 (4284 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
IKBKE Tchem Inhibitor of nuclear factor kappa B kinase epsilon subunit (3311 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
RPS6KB1 Tchem Ribosomal protein S6 kinase 1 (4456 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
CHEK1 Tchem Serine/threonine-protein kinase Chk1 (6846 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Associated Targets(non-human)
Mapk1 MAP kinase ERK2 (650 Activities)
Activity TypeRelationActivity valueUnitsAction TypeJournalPubMed IddoiAssay Aladdin ID
Mechanisms of Action
Certificates(CoA,COO,BSE/TSE and Analysis Chart)
C of A & Other Certificates(BSE/TSE, COO):
Analytical Chart:
Chemical and Physical Properties
Sensitivityheat & light &air sensitive
Specific Rotation[α]-33° (C=1,DMF)
Melt Point(°C)200°C
Molecular Weight280.300 g/mol
XLogP32.200
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count7
Rotatable Bond Count2
Exact Mass279.998 Da
Monoisotopic Mass279.998 Da
Topological Polar Surface Area136.000 Ų
Heavy Atom Count18
Formal Charge0
Complexity390.000
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
The total count of all stereochemical bonds0
Covalently-Bonded Unit Count1
Documents & Articles
Comprehensive Essay on D-Luciferin
Dual-Luciferase: Methodological Advances for Observing Two “Lights” in the Same Cell
What methods are used to measure cell proliferation?
Application Guide to Super Fluor 680 / 750 Near-Infrared Dyes for In Vivo Small-Animal Fluorescence Imaging
General Principles of Antibody Labeling with NHS-Activated Esters, F/P Calculation, and Troubleshooting Guide
Based on the Vir System: T-DNA Transfer Mechanisms and Engineering Essentials for Plant Genetic Transformation
Principles for Selecting Firefly Luciferin Substrates and Experimental Optimization Strategies
Interleukin-29 (IL-29/IFN-λ1): Molecular Features, Signaling Networks, and a Systematic Framework for Research Applications
A Comprehensive Overview of Thiazole: Structural Features, Application Value, Selection Considerations, and Product Navigation (Tables 1–4)
What Is Thiazoline? Structural Features, Functional Value, Application Areas, and Research Selection Strategies
Citations of This Product
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