alpha-Sanshool

Base Information

• Chemical Name: alpha-Sanshool
• CAS No.: 504-97-2
• Molecular Formula: C16H25NO
• Molecular Weight: 247.381
• Hs Code.: 2924199090
• UNII: YB7LBG97PX
• DSSTox Substance ID: DTXSID601319143
• Nikkaji Number: J674.640C
• Wikidata: Q2839529
• Mol file: 504-97-2.mol

Synonyms:alpha-sanshool;beta-sanshool;gamma-sanshool;sanshool

Chemical Property of alpha-Sanshool

Chemical Property:

• Vapor Pressure: 2.22E-07mmHg at 25°C
• Melting Point: 63-65 °C
• Refractive Index: 1.496
• Boiling Point: 423.5 °C at 760 mmHg
• PKA: 15.06±0.46(Predicted)
• Flash Point: 259.3 °C
• PSA: 32.59000
• Density: 0.904 g/cm³
• LogP: 4.62380
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 8
• Exact Mass: 247.193614421
• Heavy Atom Count: 18
• Complexity: 322

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=CC=CC=CCCC=CC(=O)NCC(C)C
• Isomeric SMILES: C/C=C/C=C/C=C\CC/C=C/C(=O)NCC(C)C

Technology Process of alpha-Sanshool

There total 9 articles about alpha-Sanshool 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: 53.0%

(2E,8E,10E)-N-isobutyldodeca-2,8,10-trien-6-yneamide → Alpha-Sanshool (504-97-2)

Guidance literature:

With copper diacetate; silver nitrate; zinc; In methanol; water; for 24h;

Reference yield:

trans,trans-2,4-Hexadienal (142-83-6,4488-48-6) + (E)-6-(Triphenyl-λ5-phosphanylidene)-hex-2-enoic acid isobutyl-amide (98095-55-7) → Alpha-Sanshool (504-97-2) + Beta-Sanshool (10076-00-3)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; dimethyl sulfoxide; at 0 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)94859-7

Reference yield:

hept-2-en-6-ynoic acid methyl ester (140677-99-2,141943-16-0,140677-83-4) → Alpha-Sanshool (504-97-2)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydroxide / tetrahydrofuran / 1 h / 50 °C

2: N-ethyl-N,N-diisopropylamine; diethyl cyanophosphonate / tetrahydrofuran / 1.5 h / 0 - 20 °C

3: N-Bromosuccinimide; silver nitrate / acetone / 2 h / 20 °C

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydroxide / tetrahydrofuran / 2 h / 50 °C

5: silver nitrate; zinc; copper diacetate / water; methanol / 24 h

With N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; diethyl cyanophosphonate; copper diacetate; silver nitrate; N-ethyl-N,N-diisopropylamine; sodium hydroxide; zinc; In tetrahydrofuran; methanol; water; acetone;

upstream raw materials:

2E,6Z,8E,10E-dodecatetraenoic acid

isobutylamine

trans,trans-2,4-Hexadienal

(E)-6-(Triphenyl-λ⁵-phosphanylidene)-hex-2-enoic acid isobutyl-amide

Downstream raw materials:

N-isobutyldodecanamide

Refernces

• 1、 Crombie, Leslie,Fisher, David. "SYNTHESIS OF NATURAL POLYENE ISOBUTYLAMIDES. STEREOCHEMISTRY OF THE WITTIG REACTIONS". . p. 2481 - 2484. Retrieved 2007/10/02.