Guaiol acetate

Base Information

• Chemical Name: Guaiol acetate
• CAS No.: 134-28-1
• Deprecated CAS: 17431-48-0
• Molecular Formula: C17H28 O2
• Molecular Weight: 264.408
• European Community (EC) Number: 205-135-0
• NSC Number: 46160
• UNII: 4J2P61VYV9
• DSSTox Substance ID: DTXSID7051684
• Nikkaji Number: J184.388E
• Wikidata: Q27259699
• Mol file: 134-28-1.mol

Synonyms:Guaiol acetate;Guaiac acetate;Guaiyl acetate;134-28-1;Guaiol, acetate;Guaiac wood acetate;UNII-4J2P61VYV9;4J2P61VYV9;NSC46160;NSC-46160;Octahydroazulene acetate;Guai-1(5)-en-11-ol, acetate;Guai-1-en-11-ol acetate;EINECS 205-135-0;NSC 46160;1,4-Dimethyl-7-(alpha-hydroxyisopropyl)-delta9,10-octahydroazule;1-Methyl-1-((3S,8S)-1,2,3,4,5,6,7,8-octahydro-3,8-dimethylazulen-5-yl)ethyl acetate;5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-.alpha.,.alpha.,3,8-tetramethyl-, acetate, (3S,5R,8S)-;5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,alpha-3,8-tetramethyl-, acetate, (3S-(3alpha,5alpha,8alpha))-;5-Azulenemethanol, 1,2,3,4,5alpha,6,7,8-octahydro-alpha,alpha,3beta,8beta-tetramethyl-, acetate;GUAIYL ACETATE [FHFI];SCHEMBL1666524;DTXSID7051684;CHEBI:173881;1 - methyl - 1 - ((3S,8S) - 1,2,3,4,5,6,7,8 - octahydro - 3,8 - dimethylazulen - 5 - yl)ethyl acetate;5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro- ?,?,3,8-tetramethyl-, acetate, [3S-(3?,5?,8?)]-;5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-, acetate, (3S,5R,8S)-;5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-, acetate, (3S-(3alpha,5alpha,8alpha))-;5-Azulenemethanol, 1,2,3,4,5.alpha.,6,7,8-octahydro-.alpha.,.alpha.,3.beta.,8.beta.-tetramethyl-, acetate;2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]propan-2-yl acetate;Q27259699;5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-.alpha.,.alpha.,3,8-tetramethyl-, 5-acetate, (3S,5R,8S)-;5-Azulenemethanol, 1,2,3,4,5,6,7,8-octahydro-alpha,alpha,3,8-tetramethyl-, 5-acetate, (3S,5R,8S)-;5-Azulenemethanol,2,3,4,5,6,7,8-octahydro-.alpha.,.alpha.,3,8-tetramethyl-, acetate, [3S-(3.alpha.,5.alpha.,8.alpha.)]-;5-Azulenemethanol,2,3,4,5.alpha.,6,7,8-octahydro-.alpha.,.alpha.,3.beta.,8.beta.-tetramethyl-, acetate

Chemical Property of Guaiol acetate

Chemical Property:

• Vapor Pressure: 0.000134mmHg at 25°C
• Refractive Index: n20/D 1.4905(lit.)
• Boiling Point: 333.7 °C at 760 mmHg
• Flash Point: 104 °C
• PSA: 26.30000
• Density: 0.977 g/mL at 25 °C(lit.)
• LogP: 4.49080
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 264.208930132
• Heavy Atom Count: 19
• Complexity: 392

Purity/Quality:

99%, ^*data from raw suppliers

GUAIYL ACETATE Aldrich ^*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: CC1CCC(CC2=C1CCC2C)C(C)(C)OC(=O)C
• Isomeric SMILES: C[C@H]1CC[C@H](CC2=C1CC[C@@H]2C)C(C)(C)OC(=O)C
• Description: Guaiol acetate has a faint but lasting rose odor and a sweet taste suggestive of currant. It is not very stable. Guaiol acetate may be synthesized by acetylation of guaiol, which is one of the constituents of the essential oil from guaiac wood.

Technology Process of Guaiol acetate

There total 1 articles about Guaiol acetate 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%

guaiol (489-86-1) + acetic anhydride (108-24-7) → 2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]-propan-2-yl acetate (134-28-1)

Guidance literature:

With dmap; at 150 ℃; for 6h; Inert atmosphere;

DOI:10.1021/np500611z

Reference yield:

2-[(3S,5R,8S)-3,8-dimethyl-1,2,3,4,5,6,7,8-octahydroazulen-5-yl]-propan-2-yl acetate (134-28-1) → (1S,4S,7R)-7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulene (3691-12-1,53863-54-0)

Guidance literature:

at 220 ℃; for 6h; Inert atmosphere;

DOI:10.1021/np500611z

upstream raw materials:

guaiol

acetic anhydride

Downstream raw materials:

(1S,4S,7R)-7-Isopropenyl-1,4-dimethyl-1,2,3,4,5,6,7,8-octahydro-azulene

Refernces

• 1、 Nakanishi, Akira,Fukushima, Yusuke,Miyazawa, Norio,Yoshikawa, Keisuke,Maeda, Tomoko,Kurobayashi, Yoshiko. "Identification of Rotundone as a Potent Odor-Active Compound of Several Kinds of Fruits". . p. 4464 - 4471. Retrieved 2017.