Ipsdienol

Base Information

• Chemical Name: Ipsdienol
• CAS No.: 35628-00-3
• Deprecated CAS: 13040-13-6
• Molecular Formula: C10H16O
• Molecular Weight: 152.236
• Hs Code.: 2905290000
• European Community (EC) Number: 609-154-9
• UNII: I0CK35047X
• DSSTox Substance ID: DTXSID50885627
• Nikkaji Number: J19.909E
• Wikipedia: (S)-Ipsdienol
• Wikidata: Q13422964
• Metabolomics Workbench ID: 28026
• Mol file: 35628-00-3.mol

Synonyms:2-methyl-6-methylene-2,7-octadien-4-ol;ipsdienol

Chemical Property of Ipsdienol

Chemical Property:

• Vapor Pressure: 0.0103mmHg at 25°C
• Refractive Index: 1.473
• Boiling Point: 233.6 °C at 760 mmHg
• PKA: 14?+-.0.20(Predicted)
• Flash Point: 92.2 °C
• PSA: 20.23000
• Density: 0.87 g/cm³
• LogP: 2.44580
• Storage Temp.: 2-8°C
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 173

Purity/Quality:

99%, ^*data from raw suppliers

S-Ipsdienol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CC(CC(=C)C=C)O)C
• Isomeric SMILES: CC(=C[C@H](CC(=C)C=C)O)C
• Uses: S-Ipsdienol is a terpene, which is a conspecific aggregation pheromone of the Asian larch bark beetle, Ips subelongatus. S-Ipsdienol could be used as an antioxidant and antimicrobial agent in food, pharmaceutical and pesticide industries.

Technology Process of Ipsdienol

There total 28 articles about Ipsdienol 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%

(S)-4-t-Butyldimethylsilyloxy-2-methyl-6-methyleneocta-2,7-diene (134393-22-9) → (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4020(01)96127-7

Reference yield: 71.0%

3,3-dimethyl acrylaldehyde (107-86-8) + tert-butyl (2-methylenebut-3-en-1-yl) carbonate → (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Guidance literature:

With potassium phosphate; C₅₆H₅₁IrN₂O₁₀P₂; In 1,2-dimethoxyethane; isopropyl alcohol; at 70 ℃; for 24h; enantioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1039/c8cc09706b

Reference yield: 64.0%

tert-butyl (2-methylenebut-3-en-1-yl) carbonate + 3-methyl-2-buten-1-ol (556-82-1) → (4S)-2-methyl-6-methylideneocta-2,7-dien-4-ol (35628-00-3)

Guidance literature:

With potassium phosphate; C₅₆H₅₁IrN₂O₁₀P₂; In 1,2-dimethoxyethane; at 70 ℃; for 24h; enantioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1039/c8cc09706b

upstream raw materials:

(R)-5-acetoxy-7-methyl-3-methylene-octa-1,6-diene

(-)-(1S,4S,5S)-2⁽¹⁰⁾-pinen-4-ol

L-(+)-diisopropyl tartrate

3,3-dimethyl acrylaldehyde

Refernces

• 1、 Yamamoto, Yasunori,Hara, Shoji,Suzuki, Akira. "Enantioselective synthesis of ipsenol and ipsdienol using a (2-bromoallyl)borane derivative". . p. 1029 - 1036. Retrieved 1997.
• 2、 Kovalenko,Prokhorevich. "Improved synthesis of optically active ipsdienol". . p. 757 - 758. Retrieved 2016.
• 3、 Kovalenko,Matyushenkov. "Stereoselective synthesis of (R)- and (S)-ipsdienols, pheromone components of bark beetles of the Ips family". . p. 1168 - 1172. Retrieved 2013/01/15.