Luffariellolide

Base Information

Chemical Name:Luffariellolide
CAS No.:111149-87-2
Molecular Formula:C25H38 O3
Molecular Weight:386.575
Hs Code.:
NSC Number:622149
Nikkaji Number:J247.990G
Metabolomics Workbench ID:134916
ChEMBL ID:CHEMBL451037
Mol file:111149-87-2.mol

Synonyms:luffariellolide

Suppliers and Price of Luffariellolide

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Usbiological
Luffariellolide
500ug
$ 708.00

TRC
Luffariellolide
0.5mg
$ 360.00

Cayman Chemical
Luffariellolide ≥98%
1mg
$ 120.00

ApexBio Technology
Luffariellolide
1mg
$ 166.00

AK Scientific
Luffariellolide
1mg
$ 262.00

Total 5 raw suppliers

Chemical Property of Luffariellolide

Chemical Property:

Vapor Pressure:5.39E-14mmHg at 25°C
Boiling Point:541.7°Cat760mmHg
PKA:9.98±0.40(Predicted)
Flash Point:209.3°C
PSA：46.53000
Density:1.006g/cm³
LogP:6.54780
XLogP3:6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:9
Exact Mass:386.28209507
Heavy Atom Count:28
Complexity:689

Purity/Quality:

≥98% ^*data from raw suppliers

Luffariellolide ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1=C(C(CCC1)(C)C)CCC(=CCCC(=CCCC2=CC(=O)OC2O)C)C
Isomeric SMILES:CC1=C(C(CCC1)(C)C)CC/C(=C/CC/C(=C/CCC2=CC(=O)OC2O)/C)/C
Uses Luffariellolide is a natural sesterterpenoid which reversibly inhibits secretory phospholipase A2 isoforms from bee venom (IC50 = 230 nM) and snake venom, reducing inflammation. It blocks the production of platelet-activating factor in stimulated neutrophils (IC50 = 5 μM). Luffariellolide is also a structural mimic of all-trans retinoic acid (RA) and, at 1 μM, acts as an agonist for the RA receptors RAR α, β, and γ but not for other nuclear receptors. In RA-sensitive cancer cell lines, luffariellolide induces the expression of RAR target genes and inhibits cell growth. It also inhibits the activation of hypoxia-inducible factor by hypoxia (IC50 = 3.6 μM).[Cayman Chemical] Luffariellolide is an anti-inflammatory PLA2?inhibitor.

Technology Process of Luffariellolide

There total 6 articles about Luffariellolide 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:

: 916651-17-7
C₃₄H₅₈O₂Si

: 111149-87-2
Luffariellolide

Guidance literature:: C₃₄H₅₈O₂Si; With 3,3-dimethyldioxirane; In dichloromethane; acetone; at -78 ℃;

With amberlyst-15; water; In acetone; at 20 ℃; Further stages.;
DOI:10.1055/s-2006-949641

Reference yield:

: 37905-04-7
(2E,6E)-8-bromo-3,7-dimethylocta-2,6-dienyl acetate

: 111149-87-2
Luffariellolide

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi; HMPA / tetrahydrofuran / -78 °C

2.1: 76 percent / Li; EtNH₂ / diethyl ether / -78 °C

3.1: 86 percent / N-chlorosuccinimide; dimethyl sulfide

4.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 1 h / 0 °C

4.2: Li₂CuCl₄ / tetrahydrofuran / 0 °C

5.1: dimethyldioxirane / CH₂Cl₂; acetone / -78 °C

5.2: Amberlyst-15; H₂O / acetone / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; N-chloro-succinimide; n-butyllithium; dimethylsulfide; 3,3-dimethyldioxirane; lithium; magnesium; ethylamine; ethylene dibromide; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1055/s-2006-949641

Reference yield:

: 56691-74-8
{[(2,6,6-trimethyl-1-cyclohexen-1-yl)methyl]sulfonyl}benzene

: 111149-87-2
Luffariellolide

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi; HMPA / tetrahydrofuran / -78 °C

2.1: 76 percent / Li; EtNH₂ / diethyl ether / -78 °C

3.1: 86 percent / N-chlorosuccinimide; dimethyl sulfide

4.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 1 h / 0 °C

4.2: Li₂CuCl₄ / tetrahydrofuran / 0 °C

5.1: dimethyldioxirane / CH₂Cl₂; acetone / -78 °C

5.2: Amberlyst-15; H₂O / acetone / 20 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; N-chloro-succinimide; n-butyllithium; dimethylsulfide; 3,3-dimethyldioxirane; lithium; magnesium; ethylamine; ethylene dibromide; In tetrahydrofuran; diethyl ether; dichloromethane; acetone;
DOI:10.1055/s-2006-949641