Safranal

Base Information

• Chemical Name: Safranal
• CAS No.: 116-26-7
• Molecular Formula: C10H14O
• Molecular Weight: 150.221
• Hs Code.: 2912299000
• European Community (EC) Number: 204-133-7
• UNII: 4393FR07EA
• DSSTox Substance ID: DTXSID7049398
• Nikkaji Number: J5.278G
• Wikipedia: Safranal
• Wikidata: Q424919
• Metabolomics Workbench ID: 47170
• ChEMBL ID: CHEMBL3183495
• Mol file: 116-26-7.mol

Synonyms:2,6,6-trimethyl-1,3-cyclohexadiene-1-carboxaldehyde;safranal

Chemical Property of Safranal

Chemical Property:

• Appearance/Colour: Liquid
• Vapor Pressure: 0.134mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: n20/D 1.523(lit.)
• Boiling Point: 217.3 °C at 760 mmHg
• Flash Point: 80.4 °C
• PSA: 17.07000
• Density: 0.975 g/cm³
• LogP: 2.48790
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Solubility.: Chloroform, Ethyl Acetate (Slightly), Methanol (Slightly)
• Water Solubility.: 514.9mg/L at 20℃
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 150.104465066
• Heavy Atom Count: 11
• Complexity: 231

Purity/Quality:

99.9% ^*data from raw suppliers

Safranal(>80%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(CC=C1)(C)C)C=O
• General Description: Safranal, a key intermediate in the synthesis of the A-ring building block of Taxol, is derived from inexpensive citral and serves as a major constituent of saffron oil. Its aldehyde functionality enables strategic transformations, such as reduction to an allylic alcohol and subsequent protection, facilitating the introduction of necessary stereochemistry and functional groups for Taxol analogs. This approach offers a concise and efficient route for producing Taxol derivatives with potential therapeutic advantages.

Technology Process of Safranal

There total 43 articles about Safranal 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: 92.0%

2,6,6-trimethylcyclohexa-1,3-dienecarbonitrile (72152-84-2) → safranal (116-26-7)

Guidance literature:

2,6,6-trimethylcyclohexa-1,3-dienecarbonitrile; With diisobutylaluminium hydride; In hexane; Petroleum ether; at -60 - 20 ℃; for 0.5h;

With silica gel; In water; toluene; at -20 - 0 ℃; for 1h;

DOI:10.1002/ejoc.200390130

Reference yield: 62.0%

4,5-Dibromo-4,8,8-trimethyl-1-oxa-spiro[2.5]octane → safranal (116-26-7)

Guidance literature:

With lithium carbonate; In N,N-dimethyl-formamide; at 105 ℃; for 14h;

DOI:10.1016/S0040-4020(98)83010-X

Reference yield: 39.1%

safranal (73527-25-0) → safranal (116-26-7)

Guidance literature:

With pyridine; for 2.5h; Heating;

DOI:10.1248/cpb.29.105

upstream raw materials:

1-hydroxymethyl-2,6,6-trimethylcyclohexa-1,3-diene

2,6,6-trimethylcyclohexa-1,3-dienecarbonitrile

safranal

2,6,6-trimethylcyclohex-1-enecarbaldehyde

Downstream raw materials:

2,6,6-trimethyl-cyclohexa-1,3-dienecarbaldehyde-thiosemicarbazone

2,6,6-trimethyl-cyclohexa-1,3-dienecarbaldehyde-(2,4-dinitro-phenylhydrazone)

(E)-1,1,1-Trifluoro-4-(2,6,6-trimethyl-cyclohexa-1,3-dienyl)-but-3-en-2-one

2,2-dimethylsuccinic acid

Refernces

A short synthesis of the A-ring of taxol

10.1016/0040-4020(95)00378-L

This research aims to develop a concise and efficient synthetic route for the A-ring building block of Taxol, a diterpene with significant antitumor activity but limited natural availability. The study presents a seven-step synthesis starting from an inexpensive mixture of E- and Z-citrals, which are converted to safranal through a series of reactions including cyclization, bromination, and dehydrobromination. Safranal is described as a key intermediate in the synthesis of the A-ring building block for Taxol. It is the major constituent of saffron oil and can be prepared from the inexpensive citral in a few steps. Safranal is used as a starting material to introduce the necessary functional groups and stereochemistry required for the A-ring of Taxol. The researchers reasoned that reduction of the aldehyde function of safranal to an allylic alcohol, followed by protection as the pivalate, would lead to the conjugated allylic pivalate, which could then be further transformed into the desired ketone through allylic oxidation and 1,4-reduction. The authors conclude that their method is advantageous due to its brevity and simplicity, making it a viable alternative for synthesizing the A-ring building block, especially for the development of simpler Taxol analogs with potentially better solubility and therapeutic properties.