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| CAS No.: | 2591-17-5 |
|---|---|
| Name: | D-LUCIFERIN |
| Article Data: | 32 |
| Molecular Structure: | |
|
|
|
| Formula: | C11H8N2O3S2 |
| Molecular Weight: | 280.328 |
| Synonyms: | 2-Thiazoline-4-carboxylicacid, 2-(6-hydroxy-2-benzothiazolyl)-, (-)- (8CI);4-Thiazolecarboxylic acid,4,5-dihydro-2-(6-hydroxy-2-benzothiazolyl)-, (S)-;(4S)-2-(6-Hydroxybenzothiazol-2-yl)-4,5-dihydrothiazole-4-carboxylic acid;(S)-Luciferin (firefly);Beetle luciferin;BrightGlo;D-(-)-Luciferin;D-Luciferin;Firefly luciferin;Luciferin;Luciferin (firefly); |
| EINECS: | 219-981-3 |
| Density: | 1.815 g/cm3 |
| Melting Point: | 200-204 °C |
| Boiling Point: | 587.579 °C at 760 mmHg |
| Flash Point: | 309.157 °C |
| Appearance: | off-white to light yellow powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | 36/37/38 |
| Safety: | 26-36/37/39 |
| PSA: | 136.32000 |
| LogP: | 1.38410 |
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| Conditions | Yield |
|---|---|
| In water at 20℃; | 95% |
| With ammonia; sodium In methanol; water | 94% |
| Stage #1: D-cysteine; 2-cyano-6-hydroxybenzothiazole In aq. buffer for 1h; Stage #2: With ATP; magnesium chloride; zinc(II) chloride; luciferase In aq. buffer | 27% |
| Conditions | Yield |
|---|---|
| With potassium carbonate In methanol; water for 0.333333h; Inert atmosphere; | 86% |
| With potassium carbonate In water; acetonitrile at 20℃; for 0.333333h; | 86% |
| With potassium carbonate In methanol; water for 0.0833333h; Yield given; | |
| With potassium carbonate In methanol for 8h; Concentration; Reagent/catalyst; Inert atmosphere; | 22.76g |
| Conditions | Yield |
|---|---|
| Stage #1: l-cysteine hydrochloride; 2-cyano-6-hydroxybenzothiazole In methanol; water at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: With potassium carbonate In methanol; water at 20℃; for 0.333333h; Inert atmosphere; | 86% |
| With potassium carbonate In methanol; dichloromethane; water for 0.166667h; Cooling with ice; | 80% |
| Conditions | Yield |
|---|---|
| (i) Na, liq. NH3, (ii) /BRN= 744134/, aq. MeOH; Multistep reaction; |
| Conditions | Yield |
|---|---|
| With human glutathione S-transferase P1-1 In various solvent(s) at 20℃; for 0.5h; Enzyme kinetics; Further Variations:; Reagents; |
| Conditions | Yield |
|---|---|
| With human glutathione S-transferase A1-1 In various solvent(s) at 20℃; for 0.5h; Enzyme kinetics; |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: 1.) AcOH, aq. H2SO4, aq. NaNO2, 2.) NaHCO3 / 1.) 1 h, 2.) water, 30 min 2: 81 percent / pyridinium chloride / 0.75 h / 200 °C 3: K2CO3 / methanol; H2O / 0.08 h View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 81 percent / pyridinium chloride / 0.75 h / 200 °C 2: K2CO3 / methanol; H2O / 0.08 h View Scheme | |
| Multi-step reaction with 2 steps 1: Py*HCl / 200 °C 2: (i) Na, liq. NH3, (ii) /BRN= 744134/, aq. MeOH View Scheme | |
| Multi-step reaction with 2 steps 1: pyridine hydrochloride / 1 h / 180 °C / Neat (no solvent); Inert atmosphere 2: potassium carbonate / methanol; water / 0.33 h / Inert atmosphere View Scheme |
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: dimethylsulfoxide / 2.5 h / 125 °C 2: Py*HCl / 2 h / 185 - 195 °C 3: (i) Na, liq. NH3, (ii) /BRN= 744134/, aq. MeOH View Scheme |
- 18522-99-1
ethyl 4'-methoxyoxanilate
- 2591-17-5
D-luciferin
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: (i) P2S5, xylene, (ii) K3, aq. NaOH 2: HCl 3: NH3 / methanol 4: POCl3 5: Py*HCl / 200 °C 6: (i) Na, liq. NH3, (ii) /BRN= 744134/, aq. MeOH View Scheme | |
| Multi-step reaction with 6 steps 1: (i) P2S5, xylene, (ii) K3, aq. NaOH 2: methanol; diethyl ether 3: NH3 / methanol 4: POCl3 5: Py*HCl / 200 °C 6: (i) Na, liq. NH3, (ii) /BRN= 744134/, aq. MeOH View Scheme |
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Chemistry
Molecular Structure of Firefly luciferin (CAS NO.2591-17-5):
.png)
IUPAC Name: (2Z,4S)-2-(6-oxo-1,3-benzothiazol-2-ylidene)-1,3-thiazolidine-4-carboxylic acid
Empirical Formula: C11H8N2O3S2
Molecular Weight: 280.3228
H bond acceptors: 5
H bond donors: 2
Freely Rotating Bonds: 3
Polar Surface Area: 136.32 Å2
Index of Refraction: 1.864
Molar Refractivity: 69.87 cm3
Molar Volume: 154.4 cm3
Surface Tension: 85.8 dyne/cm
Density: 1.81 g/cm3
Flash Point: 309.2 °C
Enthalpy of Vaporization: 92.27 kJ/mol
Boiling Point: 587.6 °C at 760 mmHg
Vapour Pressure: 1.19E-14 mmHg at 25°C
Melting point: 200-204 °C
Storage temp: −20°C
Merck: 13,4116
EINECS: 219-981-3
Product Categories: Heterocycles; Luciferines
InChI
InChI=1/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
Smiles
c1(C2=N[C@@H](C(=O)O)CS2)nc2ccc(cc2s1)O
Safety Profile
Hazard Codes: 
Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 3
F: 8-10
Specification
Firefly luciferin , with CAS number of 2591-17-5, can be called (2Z,4S)-2-(6-oxo-1,3-benzothiazol-2-ylidene)-1,3-thiazolidine-4-carboxylic acid ; (2E,4S)-2-(6-oxo-1,3-benzothiazol-2-ylidene)-1,3-thiazolidine-4-carboxylic acid ; 2-(6-oxo-1,3-benzothiazol-2-ylidene)-1,3-thiazolidine-4-carboxylic acid ; (4S)-2-(6-Hydroxy-1,3-benzothiazol-2-yl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid ; Luciferin . It is an off-white to light yellow powder. it should be stored in a tightly closed container under an inert atmosphere.
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