Nodakenetin

Base Information

• Chemical Name: Nodakenetin
• CAS No.: 495-32-9
• Molecular Formula: C14H14 O4
• Molecular Weight: 246.263
• UNII: PKL4EW8LPQ
• DSSTox Substance ID: DTXSID00964239
• Nikkaji Number: J15.206D
• Wikidata: Q27121472
• Metabolomics Workbench ID: 57199
• ChEMBL ID: CHEMBL1464240
• Mol file: 495-32-9.mol

Synonyms:2-(2-Hydroxy-2-propanyl)-2,3-dihydro-7H-furo(3,2-g)chromen-7-one;marmesin;marmesin, (R)-isomer;nodakenetin

Chemical Property of Nodakenetin

Chemical Property:

• Melting Point: 186.5-187 °C(Solv: benzene (71-43-2))
• Boiling Point: 434°Cat760mmHg
• PKA: 14.34±0.29(Predicted)
• Flash Point: 168°C
• PSA: 59.67000
• Density: 1.334g/cm³
• LogP: 1.86740
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 246.08920892
• Heavy Atom Count: 18
• Complexity: 387

Purity/Quality:

98% ^*data from raw suppliers

Nodakenitin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O
• Isomeric SMILES: CC(C)([C@H]1CC2=C(O1)C=C3C(=C2)C=CC(=O)O3)O
• Uses: (-)-Marmesin is a chemical compound precursor in psoralen and linear furanocoumarins biosynthesis. (-)-Marmesin has been shown to exibit antifouling activities

Technology Process of Nodakenetin

There total 55 articles about Nodakenetin 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: 64.0%

7-demethylsuberosin (21422-04-8) → marmesin (495-32-9,13710-70-8,13849-08-6,13928-55-7)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; at 0 ℃; for 3h;

DOI:10.1016/j.bmc.2011.12.002

Reference yield:

(-)-prantschimgin (13209-79-5) → 3-Methylbutenoic acid (541-47-9) + marmesin (495-32-9,13710-70-8,13849-08-6,13928-55-7)

Guidance literature:

saponification;

DOI:10.1007/BF00575188

Reference yield:

prangeferol angelate (5980-10-9,19662-71-6,36706-20-4,64911-88-2,89827-11-2,91684-52-5,106974-21-4) → Angelic acid (565-63-9) + marmesin (495-32-9,13710-70-8,13849-08-6,13928-55-7)

Guidance literature:

With potassium hydroxide; In methanol;

DOI:10.1007/BF00579495

upstream raw materials:

(S)-marmesinin

(-)-prantschimgin

6-[(2S)-2,3-dihydroxy-3-methylbutyl]-7-(trifluoromethanesulfonyl)chromen-2-one

aesculetin

Downstream raw materials:

acetic acid

recorcinol

psoralen

secorin

Refernces

• 1、 Shu, Penghua,Li, Junping,Fei, Yingying,Zhu, Huiqing,Yu, Mengzhu,Liu, Anqi,Niu, Haoying,Zou, Simin,Wei, Xialan,Ju, Zhiyu,Xu, Zhihong. "Isolation, structure elucidation, tyrosinase inhibitory, and antioxidant evaluation of the constituents from Angelica dahurica roots". . p. 456 - 462. Retrieved 2019/12/24.
• 2、 Marumoto, Shinsuke,Miyazawa, Mitsuo. "Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor". supporting information; experimental part. p. 784 - 788. Retrieved 2012/03/22.