gamma-Dodecalactone

Base Information

• Chemical Name: gamma-Dodecalactone
• CAS No.: 2305-05-7
• Deprecated CAS: 57084-18-1
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.305
• Hs Code.: 29322090
• European Community (EC) Number: 218-971-6
• NSC Number: 26511
• UNII: YX9N4581LU
• DSSTox Substance ID: DTXSID7047190
• Nikkaji Number: J35.151B
• Wikidata: Q27294762
• Metabolomics Workbench ID: 4376
• ChEMBL ID: CHEMBL195215
• Mol file: 2305-05-7.mol

Synonyms:gamma-dodecalactone

Chemical Property of gamma-Dodecalactone

Chemical Property:

• Appearance/Colour: Colourless oily liquid
• Vapor Pressure: 0.00159mmHg at 25°C
• Melting Point: 17-18 °C(lit.)
• Refractive Index: n20/D 1.452(lit.)
• Boiling Point: 294.7 °C at 760 mmHg
• Flash Point: 119.6 °C
• PSA: 26.30000
• Density: 0.931 g/cm³
• LogP: 3.44260
• Storage Temp.: Refrigerator, under inert atmosphere
• Solubility.: Chloroform (Sparingly), Methanol (Slightly)
• Water Solubility.: 60mg/L at 20℃
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 198.161979940
• Heavy Atom Count: 14
• Complexity: 166

Purity/Quality:

99% ^*data from raw suppliers

4-Dodecanolide ^*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: CCCCCCCCC1CCC(=O)O1
• Uses: 4-Dodecanolide was one of the organic compounds from meat charbroiling operations studied.

Technology Process of gamma-Dodecalactone

There total 239 articles about gamma-Dodecalactone 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: 99.0%

(S)-4-Hydroxy-dodecanoic acid benzylamide → 5(S)-octyl-2(3H)-dihydrofuranone (69830-92-8,2305-05-7)

Guidance literature:

(S)-4-Hydroxy-dodecanoic acid benzylamide; With methanol; sodium hydroxide; for 3h; Reflux;

With hydrogenchloride; In water; at 20 ℃; for 1h;

DOI:10.1080/00397910903134618

Reference yield: 92.0%

(R)-tridec-1-en-5-ol (1033405-05-8) → (R)-4-dodecanolide (69830-91-7,2305-05-7)

Guidance literature:

(R)-tridec-1-en-5-ol; With ozone; In dichloromethane; at -78 - 20 ℃;

With triphenylphosphine; In dichloromethane; at 20 ℃;

With Jones reagent; In acetone; at 0 ℃; for 1h;

DOI:10.3390/molecules24112081

Reference yield: 92.0%

C16H32O3 (935701-29-4) → (R)-4-dodecanolide (69830-91-7,2305-05-7)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; at 85 ℃; for 4h;

DOI:10.1021/ja0686211

upstream raw materials:

diazomethane

1-Decene

acetic anhydride

nonan-1-al

Downstream raw materials:

2-n-octyltetrahydrofuran

Refernces

• 1、 Vlasyuk,Voblikova,Gamalevich,Serebryakov. "The absolute configuration of (+)- And (-)-1-phenylundec-4-yn-3-ols. Synthesis of (R)-4-dodecanolide, a component of the defensive secretion of rove beetle Bledius mandibullaris". . p. 2032 - 2036. Retrieved 2013.
• 2、 Itoh,Ohta,Sano. "An efficient preparation of the optically active γ-hydroxy stannanes using lipase-catalyzed hydrolysis". . p. 6387 - 6390. Retrieved 1990.
• 3、 Taylor, Stephen K.,Arnold, Carrie R.,Gerds, Aaron T.,Ide, Nathan D.,Law, Keri M.,Kling, Dale L.,Pridgeon, Matthew G.,Simons, Lloyd J.,Vyvyan, James R.,Yamaoka, Jennifer S.,Liao, Min-Ken,Goyne, Thomas E.. "Lactone synthesis via biotransformations of γ-hydroxyamides". . p. 3819 - 3821. Retrieved 2004.
• 4、 Zhang, Chao,Pan, Jiang,Li, Chun-Xiu,Bai, Yun-Peng,Xu, Jian-He. "Asymmetric bioreduction of keto groups of 4- and 5-Oxodecanoic acids/esters with a new carbonyl reductase". . p. 35 - 39. Retrieved 2017.
• 5、 -. "MODIFIED AMINE LIPIDS". . . Retrieved 2020/07/04.
• 6、 Chen, Meng,Zhang, Xiao-Yan,Xing, Chen-Guang,Zhang, Chao,Zheng, Yu-Cong,Pan, Jiang,Xu, Jian-He,Bai, Yun-Peng. "Efficient Stereoselective Synthesis of Structurally Diverse γ- and δ-Lactones Using an Engineered Carbonyl Reductase". . p. 2600 - 2606. Retrieved 2019/05/21.