Ambrettolide

Base Information

• Chemical Name: Ambrettolide
• CAS No.: 123-69-3
• Deprecated CAS: 17598-28-6
• Molecular Formula: C16H28O2
• Molecular Weight: 252.397
• Hs Code.: 2932999099
• European Community (EC) Number: 204-644-5
• UNII: 095I377U8F
• DSSTox Substance ID: DTXSID20881237
• Nikkaji Number: J52.303H,J10.068D
• Wikidata: Q4064043
• Metabolomics Workbench ID: 44680
• ChEMBL ID: CHEMBL3727440
• Mol file: 123-69-3.mol

Synonyms:ambrettolide

Chemical Property of Ambrettolide

Chemical Property:

• Vapor Pressure: 1.39E-06mmHg at 25°C
• Refractive Index: 1.444
• Boiling Point: 399.21 °C at 760 mmHg
• Flash Point: 168.197 °C
• PSA: 26.30000
• Density: 0.894 g/cm³
• LogP: 4.78060
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 252.208930132
• Heavy Atom Count: 18
• Complexity: 233

Purity/Quality:

99%, ^*data from raw suppliers

MuskAmbrette(Natural) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCCCOC(=O)CCCCCC=CCCC1
• Isomeric SMILES: C1CCCCOC(=O)CCCCC/C=C\CCC1
• Description: Although used at one time in fruit flavors, is more extensively used in perfumes and fragrances. The use of musk ambrette has been discontinued due to the toxic nature of the substance. It was removed from GRAS status by FEMA in 1984.
• Uses: Musk ambrette is previously used as fragrance and fixative in after-shave lotions, perfumes, food flavor, etc. Musk Ambrette is a reactant in the preparation of musk macrolactones, catalyzed by Candida antartica lipase B (Novozym 435).

Technology Process of Ambrettolide

There total 27 articles about Ambrettolide 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: 98.0%

7-Hexadecin-16-olid (88785-34-6) → 7-hexadecenoic acid-16-hydroxy-O-lactone (123-69-3)

Guidance literature:

With hydrogen; Lindlar's catalyst;

Reference yield: 83.0%

(Z)-ethyl 16-hydroxyhexadec-7-enoate → 7-hexadecenoic acid-16-hydroxy-O-lactone (123-69-3)

Guidance literature:

With Lipase B immobilized on acrylic resin from Candida antarctica; In cyclohexane; water; at 40 ℃; for 3h; Enzymatic reaction;

DOI:10.1016/j.tet.2015.03.007

Reference yield: 81.0%

cis-16-iodohexadec-7-enoic acid (83345-27-1) → 7-hexadecenoic acid-16-hydroxy-O-lactone (123-69-3)

Guidance literature:

With caesium carbonate; In dimethyl sulfoxide; at 80 ℃; for 7h;

upstream raw materials:

(2E,7Z)-2,7-Hexadecadien-16-olid

cis-16-iodohexadec-7-enoic acid

16-hydroxy-Z-7-hexadecenoic acid

7-Hexadecin-16-olid

Refernces

• 1、 Fortunati, Tancredi,D'Acunto, Mariantonietta,Caruso, Tonino,Spinella, Aldo. "Chemoenzymatic preparation of musky macrolactones". . p. 2357 - 2362. Retrieved 2015/03/30.
• 2、 Rosebrugh, Lauren E.,Herbert, Myles B.,Marx, Vanessa M.,Keitz, Benjamin K.,Grubbs, Robert H.. "Highly active ruthenium metathesis catalysts exhibiting unprecedented activity and Z-selectivity". supporting information. p. 1276 - 1279. Retrieved 2013/03/14.