Carotol

Base Information

• Chemical Name: Carotol
• CAS No.: 465-28-1
• Molecular Formula: C15H26 O
• Molecular Weight: 222.37
• Hs Code.: 2906299090
• European Community (EC) Number: 866-557-4
• UNII: NT5C9M36DE
• DSSTox Substance ID: DTXSID101318114
• Nikkaji Number: J9.370J
• Wikipedia: Carotol
• Wikidata: Q5045553
• Metabolomics Workbench ID: 28386
• Mol file: 465-28-1.mol

Synonyms:Carotol;465-28-1;(+)-Carotol;UNII-NT5C9M36DE;(+)-8-Daucen-5-ol;NT5C9M36DE;Carotol, (+)-;3aalpha(1H)-Azulenol, 2,3,4,5,8,8a-hexahydro-3alpha-isopropyl-6,8aalpha-dimethyl-, (+)-;CAROTOL [MI];CHEBI:3431;SCHEMBL6514107;2,3,4,5,8,8a-hexahydro-3-isopropyl-6,8a-dimethyl-3a(1h)-azulenol;(3R,3aS,8aR)-2,3,4,5,8,8a-Hexa-hydro-6,8a-dimethyl-3-(1-methylethyl)-3a(1H)-azulenol;DTXSID101318114;LMPR0103550001;(3R,3aS,8aR)-6,8a-dimethyl-3-propan-2-yl-1,2,3,4,5,8-hexahydroazulen-3a-ol;C09628;Q5045553;(3R,3AS,8AR)-2,3,4,5,8,8A-HEXAHYDRO-6,8A-DIMETHYL-3-(1-METHYLETHYL)-3A(1H)-AZULENOL;3A(1H)-AZULENOL, 2,3,4,5,8,8A-HEXAHYDRO-6,8A-DIMETHYL-3-(1-METHYLETHYL)-, (3R,3AS,8AR)-;3a(1H)-Azulenol, 2,3,4,5,8,8a-hexahydro-6,8a-dimethyl-3-(1-methylethyl)-, (3R-(3alpha,3aalpha,8aalpha))-

Chemical Property of Carotol

Chemical Property:

• Vapor Pressure: 0.000154mmHg at 25°C
• Melting Point: <25 °C
• Refractive Index: nD20 1.4964
• Boiling Point: 295.8°Cat760mmHg
• PKA: 15.03±0.70(Predicted)
• Flash Point: 126.1°C
• PSA: 20.23000
• Density: 0.973g/cm³
• LogP: 3.92000
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 222.198365449
• Heavy Atom Count: 16
• Complexity: 305

Purity/Quality:

99% ^*data from raw suppliers

CAROTOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCC2(CCC(C2(CC1)O)C(C)C)C
• Isomeric SMILES: CC1=CC[C@]2(CC[C@@H]([C@]2(CC1)O)C(C)C)C
• Uses: (+)-Carotol is an essential oil extracted from Seseli libanotis plant. A natural product.

Technology Process of Carotol

There total 11 articles about Carotol 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:

C25H34O3 → carotol (465-28-1)

Guidance literature:

Multi-step reaction with 10 steps

1.1: toluene / 24 h / 70 °C / Inert atmosphere; Darkness

1.2: 15 h / 40 °C / Inert atmosphere

2.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 6 h

3.1: water / acetone / 2 h / 0 - 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C / Inert atmosphere

4.2: 2 h / 0 °C / Inert atmosphere

4.3: 22 h / 0 - 20 °C / Inert atmosphere

5.1: 5% palladium on Al₂O₃; hydrogen / ethyl acetate / 5 h / 20 °C

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Reflux; Inert atmosphere

7.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

7.2: 1.25 h / -78 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

9.1: Martins sulfurane / dichloromethane / 0.75 h / 0 - 20 °C / Inert atmosphere

10.1: Grubbs catalyst first generation / dichloromethane / 9 h / Reflux; Inert atmosphere

With Grubbs catalyst first generation; platinum(IV) oxide; n-butyllithium; Martins sulfurane; 5% palladium on Al₂O₃; tetrabutyl ammonium fluoride; water; hydrogen; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; acetone; toluene; 7.1: |Wittig Olefination;

DOI:10.1021/acs.orglett.6b02023

Reference yield:

C26H36O2 → carotol (465-28-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 6 h

2.1: water / acetone / 2 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C / Inert atmosphere

3.2: 2 h / 0 °C / Inert atmosphere

3.3: 22 h / 0 - 20 °C / Inert atmosphere

4.1: 5% palladium on Al₂O₃; hydrogen / ethyl acetate / 5 h / 20 °C

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Reflux; Inert atmosphere

6.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

6.2: 1.25 h / -78 °C / Inert atmosphere

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

8.1: Martins sulfurane / dichloromethane / 0.75 h / 0 - 20 °C / Inert atmosphere

9.1: Grubbs catalyst first generation / dichloromethane / 9 h / Reflux; Inert atmosphere

With Grubbs catalyst first generation; platinum(IV) oxide; n-butyllithium; Martins sulfurane; 5% palladium on Al₂O₃; tetrabutyl ammonium fluoride; water; hydrogen; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; acetone; 6.1: |Wittig Olefination;

DOI:10.1021/acs.orglett.6b02023

Reference yield:

(-)-(2R,5R)-2-(2-hydroxyethyl)-5-isopropyl-2-methylcyclopentanone → carotol (465-28-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 - 0 °C / Inert atmosphere

1.2: 2 h / 0 °C / Inert atmosphere

1.3: 22 h / 0 - 20 °C / Inert atmosphere

2.1: 5% palladium on Al₂O₃; hydrogen / ethyl acetate / 5 h / 20 °C

3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 3 h / Reflux; Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: 1.25 h / -78 °C / Inert atmosphere

5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

6.1: Martins sulfurane / dichloromethane / 0.75 h / 0 - 20 °C / Inert atmosphere

7.1: Grubbs catalyst first generation / dichloromethane / 9 h / Reflux; Inert atmosphere

With Grubbs catalyst first generation; n-butyllithium; Martins sulfurane; 5% palladium on Al₂O₃; tetrabutyl ammonium fluoride; hydrogen; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; hexane; dichloromethane; ethyl acetate; 4.1: |Wittig Olefination;

DOI:10.1021/acs.orglett.6b02023

upstream raw materials:

(1aR,3aR,8aR)-1a-Isopropyl-3a,6-dimethyl-2,3,3a,4,7,8-hexahydro-1aH-1-oxa-cyclopropa[c]azulene

Downstream raw materials:

daucalene

(1R,4R,5S,7S,8S)-7-acetyl-5,8-dihydroxy-4-isopropyl-1-methylbicyclo[4.3.0]nonane

Dihydrocarotol

Refernces