(-)-Hinesol

Base Information

• Chemical Name: (-)-Hinesol
• CAS No.: 23811-08-7
• Deprecated CAS: 4895-33-4,26934-83-8
• Molecular Formula: C15H26O
• Molecular Weight: 222.371
• Hs Code.: 2906199090
• Nikkaji Number: J17.194H
• Wikidata: Q27149875
• Metabolomics Workbench ID: 140268
• ChEMBL ID: CHEMBL505813
• Mol file: 23811-08-7.mol

Synonyms:2R-(2alpha,5beta)(R*)-isomer of hinesol;agarospirol;hinesol

Chemical Property of (-)-Hinesol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 59-60 °C
• Refractive Index: 1.505
• Boiling Point: 312.188 °C at 760 mmHg
• PKA: 15.14±0.29(Predicted)
• Flash Point: 114.626 °C
• PSA: 20.23000
• Density: 0.962 g/cm³
• LogP: 3.92000
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 222.198365449
• Heavy Atom Count: 16
• Complexity: 303

Purity/Quality:

≥98% ^*data from raw suppliers

Hinesol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCC=C(C12CCC(C2)C(C)(C)O)C
• Isomeric SMILES: C[C@H]1CCC=C([C@]12CC[C@H](C2)C(C)(C)O)C
• Uses: Hinesol can be found in various essential oils that show antifugual activities (oils from agarwood of Aquilaria sinensis ), antimicrobial activities (oils from the Phebalium squamulosum species complex), anti-inflammatory activities ( oils from agarwood of Aquilaria agallocha) and anticancer activities (oil from Cedrelopsis grevei leaves). However, no reference shows that Hinesol is responsible for any of the above activities.

Technology Process of (-)-Hinesol

There total 146 articles about (-)-Hinesol 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: 94.0%

methylmagnesium bromide (75-16-1) + (2R,5S,10S)-6,10-Dimethyl-spiro[4.5]dec-6-ene-2-carboxylic acid methyl ester (599164-90-6,797055-37-9) → (-)-hinesol (23811-08-7,26934-83-8,4895-33-4)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; for 3.5h;

DOI:10.1021/jo034281f

Reference yield: 94.0%

methylmagnesium bromide (75-16-1) + (2R,5S,10S)-6,10-Dimethyl-spiro[4.5]dec-6-ene-2-carboxylic acid methyl ester (797055-37-9) → (2RS,5SR,10SR)-hinesol (1460-73-7,19890-17-6,19890-18-7,23811-08-7,59331-07-6,59331-08-7,66537-53-9,121840-72-0,26934-83-8,4895-33-4)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; for 3.5h;

DOI:10.1021/jo034281f

Reference yield: 92.0%

Phenyl-carbamic acid 1-((2R,5S,10S)-6,10-dimethyl-spiro[4.5]dec-6-en-2-yl)-1-methyl-ethyl ester → (2RS,5SR,10SR)-hinesol (1460-73-7,19890-17-6,19890-18-7,23811-08-7,59331-07-6,59331-08-7,66537-53-9,121840-72-0,26934-83-8,4895-33-4)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 3h; Heating;

DOI:10.1246/bcsj.68.2393

upstream raw materials:

methylmagnesium bromide

(2R,5S,10S)-6,10-Dimethyl-spiro[4.5]dec-6-ene-2-carboxylic acid methyl ester

(S)-3-methyl-2-methylenecyclohexanone

methyl (2R,5S,10S)-10-methyl-6-oxo-spiro[4.5]decane-2-carboxylate

Refernces

• 1、 Nakazaki, Atsuo,Era, Tomohiro,Numada, Yuko,Kobayashi, Susumu. "Stereoselective total synthesis of (±)-α-vetispirene, (±)-hinesol, and (±)-β-vetivone based on a Claisen rearrangement". . p. 6264 - 6271. Retrieved 2007/10/03.
• 2、 Du, Yishu,Lu, Xiyan. "A phosphine-catalyzed [3+2] cycloaddition strategy leading to the first total synthesis of (-)-hinesol". . p. 6463 - 6465. Retrieved 2007/10/03.