Latia luciferin

Base Information

• Chemical Name: Latia luciferin
• CAS No.: 21730-91-6
• Molecular Formula: C15H24O2
• Molecular Weight: 236.354
• Hs Code.: 2915120000
• UNII: 15DW906925
• DSSTox Substance ID: DTXSID40415058
• Metabolomics Workbench ID: 28229
• Nikkaji Number: J15.890I,J47.289A
• Wikidata: Q27102292
• Mol file: 21730-91-6.mol

Synonyms:Latia luciferin;21730-91-6;latiluciferin;LUCIFERIN (LATIA);(9E)-7,8-dihydro-10-apo-beta-caroten-10-yl formate;(1E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-1-enyl formate;1-Buten-1-ol, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, formate, (1E)-;15DW906925;(E)-2-Methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-1-en-1-yl formate;starbld0003242;[(E)-2-methyl-4-(2,6,6-trimethylcyclohexen-1-yl)but-1-enyl] formate;C02293;SCHEMBL10306595;CHEBI:17269;DTXSID40415058;MJURCEOLOMHLAX-ZRDIBKRKSA-N;UNII-15DW906925;AKOS040752432;LMPR0103050003;Q27102292;[(E)-2-methyl-4-(2,6,6-trimethyl-1-cyclohexenyl)but-1-enyl] formate;2-(3-FORMYLOXYMETHYLENE)-BUTYL-1,3,3-TRIMETHYLCYCLOHEX-1-ENE;(1E)-2-Methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-1-butenyl formate #;1-Buten-1-ol, 2-methyl-4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, formate, (E)-

Chemical Property of Latia luciferin

Chemical Property:

• Vapor Pressure: 0.000896mmHg at 25°C
• Boiling Point: 313.8°C at 760 mmHg
• Flash Point: 128.7°C
• PSA: 26.30000
• Density: 0.927g/cm³
• LogP: 5.00590
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 236.177630004
• Heavy Atom Count: 17
• Complexity: 335

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CCC1)(C)C)CCC(=COC=O)C
• Isomeric SMILES: CC1=C(C(CCC1)(C)C)CC/C(=C/OC=O)/C

Technology Process of Latia luciferin

There total 4 articles about Latia 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:

4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on (17283-81-7) → luciferin (latia) (21730-91-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / LiHMDS / tetrahydrofuran / 5 h / Heating

2: 100 percent / DIBALH / toluene / 0 °C

3: 95 percent / MnO₂ / CH₂Cl₂ / 2 h / 20 °C

4: 45 percent / SeO₂; H₂O₂ / 2-methyl-butan-2-ol / 0 °C

With manganese(IV) oxide; selenium(IV) oxide; dihydrogen peroxide; diisobutylaluminium hydride; lithium hexamethyldisilazane; In tetrahydrofuran; tert-Amyl alcohol; dichloromethane; toluene; 1: Horner-Emmons olefination / 4: Baeyer-Villiger oxidation;

DOI:10.1246/bcsj.78.1197

Reference yield:

(E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)pent-2-en-1-ol (18665-81-1) → luciferin (latia) (21730-91-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / MnO₂ / CH₂Cl₂ / 2 h / 20 °C

2: 45 percent / SeO₂; H₂O₂ / 2-methyl-butan-2-ol / 0 °C

With manganese(IV) oxide; selenium(IV) oxide; dihydrogen peroxide; In tert-Amyl alcohol; dichloromethane; 2: Baeyer-Villiger oxidation;

DOI:10.1246/bcsj.78.1197

Reference yield:

ethyl (E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)pent-2-enoate (42569-33-5) → luciferin (latia) (21730-91-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / DIBALH / toluene / 0 °C

2: 95 percent / MnO₂ / CH₂Cl₂ / 2 h / 20 °C

3: 45 percent / SeO₂; H₂O₂ / 2-methyl-butan-2-ol / 0 °C

With manganese(IV) oxide; selenium(IV) oxide; dihydrogen peroxide; diisobutylaluminium hydride; In tert-Amyl alcohol; dichloromethane; toluene; 3: Baeyer-Villiger oxidation;

DOI:10.1246/bcsj.78.1197

upstream raw materials:

4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on

(E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)pent-2-en-1-ol

ethyl (E)-3-methyl-5-(2',6',6'-trimethylcyclohex-1'-en-1'-yl)pent-2-enoate

Downstream raw materials:

4-(2,6,6-Trimethyl-cyclohex-1-enyl)-butan-2-on

2-(4-methoxy-3-methylbut-3-enyl)-1,3,3-trimethylcyclohex-1-ene

2‐methyl‐4‐(2,6,6‐trimethylcyclohex‐1‐en‐1‐yl)butanal

Refernces

• 1、 Kojima, Satoshi,Maki, Shojiro,Hirano, Takashi,Ohmiya, Yoshihiro,Niwa, Haruki. "Bioluminescence activity of Latia luciferin analogs". . p. 4409 - 4413. Retrieved 2007/10/03.