Lespedin

Base Information

• Chemical Name: Lespedin
• CAS No.: 482-38-2
• Molecular Formula: C27H30O14
• Molecular Weight: 578.527
• Hs Code.: 29389090
• UNII: VPV01U3R59
• DSSTox Substance ID: DTXSID90197458
• Nikkaji Number: J94.496C
• Wikipedia: Kaempferitrin
• Wikidata: Q6345965
• ChEMBL ID: CHEMBL251766
• Mol file: 482-38-2.mol

Synonyms:3,7-bis-(alpha-6-deoxymannopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)chromen-4-one;kaempferitrin;kaempferol 3,7-dirhamnoside;lespedin;lespenefril;lespenephril

Chemical Property of Lespedin

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 202～203℃
• Refractive Index: 1.725
• Boiling Point: 908.6 °C at 760 mmHg
• PKA: 5.81±0.40(Predicted)
• Flash Point: 302.8 °C
• PSA: 228.97000
• Density: 1.7 g/cm³
• LogP: -0.71620
• Storage Temp.: -20°C
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 8
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 5
• Exact Mass: 578.16355563
• Heavy Atom Count: 41
• Complexity: 968

Purity/Quality:

98%,99%, ^*data from raw suppliers

Kaempferitrin ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)OC4C(C(C(C(O4)C)O)O)O)C5=CC=C(C=C5)O)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=CC(=C3C(=C2)OC(=C(C3=O)O[C@H]4[C@@H]([C@@H]([C@H]([C@@H](O4)C)O)O)O)C5=CC=C(C=C5)O)O)O)O)O
• Description: Kaempferitrin is a flavonoid glycoside that has been found in B. pinnatum and has diverse biological activities. It scavenges DPPH radicals (IC50 = 8.73 μg/ml) and is active against the bacteria S. aureus, P. aeruginosa, and S. typhi, as well as the fungi C. albicans, C. parapsilosis, and C. neoformans (MICs = 16-32 μg/ml). Kaempferitrin inhibits LPS-and IFN-γ-induced nitric oxide (NO) production in isolated mouse macrophages (IC50 = 40 μM). It decreases blood glucose levels in a rat model of alloxan-induced diabetes when administered at a dose of 100 mg/kg.
• Uses: Kaempferitirin is a glycoside of Kaempferol (K100000), a plant flavonoid that exhibits antioxidant properties and is known to reduce risks of various types cancer and cardiovascular diseases. Kaempferitirin have been isolated as natural products from plants such as Hedyotis Verticilata.

Technology Process of Lespedin

There total 15 articles about Lespedin 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: 96.0%

C58H52O22 (1374991-37-3) → kaempferitrin (482-38-2)

Guidance literature:

With methanol; potassium carbonate; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.tetlet.2012.03.103

Reference yield:

grosvenorine → kaempferol 3-rhamnoside (482-39-3,22334-39-0,28978-08-7) + kaempferol (520-18-3) + kaempferol-7-O-α-L-rhamnoside (5041-97-4,20196-89-8) + kaempferitrin (482-38-2)

Guidance literature:

With human fecal intestinal bacterial suspension; GAM media; In water; at 37 ℃; for 6h; Sealed tube; Enzymatic reaction;

DOI:10.1002/cbdv.201400397

Reference yield:

4'-benzyloxy-3,7-O-(2'',3'',4''-triacetyloxy-α-L-rhamnopyranosyl)-5-[((4-methylphenyl)sulfonyl)oxy]flavone (943827-57-4) → kaempferitrin (482-38-2)

Guidance literature:

4'-benzyloxy-3,7-O-(2'',3'',4''-triacetyloxy-α-L-rhamnopyranosyl)-5-[((4-methylphenyl)sulfonyl)oxy]flavone; With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 14h;

With potassium carbonate; In methanol; at 70 ℃; for 1.5h; Further stages.;

DOI:10.1021/jo070502w

upstream raw materials:

4'-benzyloxy-3,7-O-(2'',3'',4''-triacetyloxy-α-L-rhamnopyranosyl)-5-[((4-methylphenyl)sulfonyl)oxy]flavone

4'-benzyloxy-3-methoxy-7-(methoxymethyloxy)-5-[((4-methylphenyl)sulfonyl)oxy]flavone

4'-benzyloxy-3,7-dihydroxy-5-[((4-methylphenyl)sulfonyl)oxy]flavone

2-methoxy-1-[2-hydroxy-4,6-bis(methoxymethyloxy)phenyl]ethanone

Downstream raw materials:

L-rhamnose

kaempferol

D-quionovose

(2S,3S)-3,40,5,7-tetrahydroxyflavanone

Refernces

• 1、 Yang, Weizhun,Sun, Jiansong,Yang, Zhongyi,Han, Wei,Zhang, Wei-Dong,Yu, Biao. "Efficient synthesis of kaempferol 3,7-O-bisglycosides via successive glycosylation with glycosyl ortho-alkynylbenzoates and trifluoroacetimidates". . p. 2773 - 2776. Retrieved 2012/07/17.