Hydroxycitronellol

Base Information

• Chemical Name: Hydroxycitronellol
• CAS No.: 107-74-4
• Deprecated CAS: 1321-91-1
• Molecular Formula: C₁₀H₂₂O₂
• Molecular Weight: 174.283
• European Community (EC) Number: 203-517-1
• NSC Number: 406140,67886
• UNII: R0B4U2I48W
• DSSTox Substance ID: DTXSID6044513
• Nikkaji Number: J26.180G
• Wikidata: Q27287607
• RXCUI: 1313707
• Metabolomics Workbench ID: 44199
• ChEMBL ID: CHEMBL3187980
• Mol file: 107-74-4.mol

Synonyms:3,7-dimethyl-1,7-octanediol;3,7-dimethyloctane-1,7-diol;hydroxycitronellol;hydroxydihydrocitronellol

Chemical Property of Hydroxycitronellol

Chemical Property:

• Vapor Pressure: 0.00139mmHg at 25°C
• Melting Point: 47.36°C (estimate)
• Refractive Index: 1.455
• Boiling Point: 252.5°Cat760mmHg
• PKA: 15.14±0.10(Predicted)
• Flash Point: 108.5°C
• PSA: 40.46000
• Density: 0.918g/cm³
• LogP: 1.94610
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 174.161979940
• Heavy Atom Count: 12
• Complexity: 110

Purity/Quality:

98% ^*data from raw suppliers

3,7-DIMETHYL-1,7-OCTANEDIOL 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Oils and Extracts
• Canonical SMILES: CC(CCCC(C)(C)O)CCO
• Description: Hydroxyeitronellol has an odor reminiscent of rose and grape hyacinth. May be prepared by hydrogenation (under pressure in presence of Raney Ni) of 3,7-dimethyl-7-hydroxy-octan-l-al; also in good yields by catalytic hydrogenation (using Raney Ni) of 1.2-epoxy-3,7-dimethyl-octan-7-ol.

Technology Process of Hydroxycitronellol

There total 22 articles about Hydroxycitronellol 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%

7-hydroxy-3,7-dimethyl-octanal (107-75-5) → 7-hydroxycitronellol (98206-63-4,122612-23-1,107-74-4)

Guidance literature:

With trimethylamine-N-oxide; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one) irontricarbonyl complex3; potassium formate; In ethanol; at 45 - 60 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.tet.2021.132187

Reference yield: 98.0%

Acetic acid 7-acetoxy-1,1,5-trimethyl-heptyl ester → 7-hydroxycitronellol (98206-63-4,122612-23-1,107-74-4) + 8-hydroxy-2,6-dimethyloct-2-yl acetate

Guidance literature:

With magnesium methanolate; In methanol; for 10h; Yields of byproduct given; Ambient temperature;

DOI:10.1021/jo961257b

Reference yield: 75.0%

Citronellol (106-22-9) → 7-hydroxycitronellol (98206-63-4,122612-23-1,107-74-4)

Guidance literature:

With iron(III)-acetylacetonate; methyl 4-nitrobenzenesulfonate; phenylsilane; sodium hydrogencarbonate; In methanol; at 0 - 20 ℃; for 12h; regioselective reaction; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.202015740

upstream raw materials:

ethanol

(R)-7-hydroxy-3,7-dimethyl-octanal

aluminum ethoxide

(3R)-citronellol

Downstream raw materials:

7-hydroxy-3,7-dimethyl-octanal

2,6-dimethyl-hept-6-en-2-ol

Refernces

• 1、 Beckwith,A.L.J. et al.. "-". . p. 2177 - 2188. Retrieved 1977.
• 2、 Wang, Daoyong,Shuler, William G.,Pierce, Conor J.,Hilinski, Michael K.. "An Iminium Salt Organocatalyst for Selective Aliphatic C-H Hydroxylation". . p. 3826 - 3829. Retrieved 2016.
• 3、 Coufourier, Sébastien,Ndiaye, Daouda,Gaillard, Quentin Gaignard,Bettoni, Léo,Joly, Nicolas,Mbaye, Mbaye Diagne,Poater, Albert,Gaillard, Sylvain,Renaud, Jean-Luc. "Iron-catalyzed chemoselective hydride transfer reactions". supporting information. . Retrieved 2021/06/07.
• 4、 Coufourier, Sébastien,Gaillard, Sylvain,Mbaye, Mbaye Diagne,Ndiaye, Daouda,Renaud, Jean-Luc. "Cyclopentadienone iron tricarbonyl complexes-catalyzed hydrogen transfer in water". supporting information. . Retrieved 2020/01/28.