Senkyunolide A

Base Information

• Chemical Name: Senkyunolide A
• CAS No.: 63038-10-8
• Deprecated CAS: 62006-39-7
• Molecular Formula: C12H16O2
• Molecular Weight: 192.258
• Hs Code.: 2932209090
• UNII: 74QZK813SO
• DSSTox Substance ID: DTXSID40212322
• Nikkaji Number: J19.102G
• Wikidata: Q27266299
• Mol file: 63038-10-8.mol

Synonyms:3-N-butyl-4,5-dihydrophthalide;3-N-butyl-4,5-dihydrophthalide, (S)-isomer;NBPA;sedanenolide;senkyunolide;senkyunolide A

Chemical Property of Senkyunolide A

Chemical Property:

• Vapor Pressure: 1.3E-05mmHg at 25°C
• Boiling Point: 368.1°C at 760 mmHg
• Flash Point: 154.2°C
• PSA: 26.30000
• Density: 1.07g/cm³
• LogP: 2.74860
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 192.115029749
• Heavy Atom Count: 14
• Complexity: 299

Purity/Quality:

99% ^*data from raw suppliers

Senkyunolide A ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC1C2=C(C=CCC2)C(=O)O1
• Isomeric SMILES: CCCC[C@H]1C2=C(C=CCC2)C(=O)O1
• Description: Senkyunolide A is a phthalide originally isolated from celery seed essential oil that has cytoprotective and antiproliferative activities. It protects against cell injury induced by corticosterone in PC12 cells in a time-dependent manner when used at concentrations ranging from 0.125 to 0.5 mg/ml and reduces corticosterone-induced apoptosis at a concentration of 0.5 mg/ml. It also reverses increases in protein levels of phosphatase 2A (PP2A) and α-synuclein and reverses decreases in the phosphorylated forms of PP2A and α-synuclein. Senkyunolide A inhibits cell proliferation of HT-29 colon cancer (IC50 = 54.17 μM) but not non-cancerous human CCD-18Co colon cells (IC50 = 109.11 μM).

Technology Process of Senkyunolide A

There total 4 articles about Senkyunolide A 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: 43.0%

(S)-(-)-1-ethynylpentyl 2,4-pentadienoate (1020260-46-1) → (S)-3-butyl-4,5-dihydroisobenzofuran-1(3H)-one (63038-10-8,62006-39-7) + (S)-3-n-butylphthalide (3413-15-8)

Guidance literature:

With Santonox R; In toluene; at 220 ℃; for 9h; Autoclave; Inert atmosphere;

DOI:10.1271/bbb.110206

Reference yield:

senkyunolide P (117005-27-3,142864-23-1) → Z-ligustilide (81944-09-4) + (S)-3-butyl-4,5-dihydroisobenzofuran-1(3H)-one (63038-10-8,62006-39-7)

Guidance literature:

at 220 - 250 ℃; under 3 Torr; Yield given. Yields of byproduct given;

DOI:10.3987/COM-91-5877

Reference yield:

C12H10O3 → (S)-3-butyl-4,5-dihydroisobenzofuran-1(3H)-one (63038-10-8,62006-39-7) + (S)-3-n-butylphthalide (3413-15-8)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; triethylamine / tetrahydrofuran / 0.5 h / 10 - 20 °C

2: Santonox R / toluene / 9 h / 220 °C / Autoclave; Inert atmosphere

With dmap; Santonox R; triethylamine; In tetrahydrofuran; toluene; 2: Diels-Alder reaction;

DOI:10.1271/bbb.110206

upstream raw materials:

senkyunolide P

(S)-(-)-1-ethynylpentyl 2,4-pentadienoate

1,3-butadiene-1-carboxylic acid

Downstream raw materials:

Senkyunolide J p-bromobenzoate

Senkyunolide N p-bromobenzoate

senkyunolide-J

Senkyunolide N

Refernces

• 1、 Naito, Takashi,Katsuhara, Takao,Niitsu, Kazuaki,Ikeya, Yukinobu,Okada, Minoru,Mitsuhashi, Late Hiroshi. "PHTHALIDE DIMERS FROM LIGUSTICUM CHUANGXIONG Hort.". . p. 2433 - 2442. Retrieved 2007/10/02.