107-74-4

Basic information

• Product Name: HYDROXYCITRONELLOL
• Synonyms: FEMA 2586;HYDROXYCITRONELLOL;HYDROXYOL;3,7-DIMETHYL-OCTANE-1,7-DIOL;3 7-DIMETHYL-1 7-OCTANEDIOL;(R)-3,7-dimethyl-octane-1,7-diol;3,7-dimethyl-7-hydroxy-1-octano;3,7-dimethyl-7-octanediol
• CAS NO: 107-74-4
• Molecular Formula: C₁₀H₂₂O₂
• Molecular Weight: 174.28
• EINECS: 203-517-1
• Mol File: 107-74-4.mol
• Article Data: 15

Chemical Properties

• Melting Point: 47.36°C (estimate)
• Boiling Point: 252.5°C
• Flash Point: 108.5°C
• Appearance: /
• Density: 0.9180
• Vapor Pressure: 0.00139mmHg at 25°C
• Refractive Index: 1.4599
• PKA: 15.14±0.10(Predicted)
• CAS DataBase Reference: HYDROXYCITRONELLOL(CAS DataBase Reference)
• NIST Chemistry Reference: HYDROXYCITRONELLOL(107-74-4)
• EPA Substance Registry System: HYDROXYCITRONELLOL(107-74-4)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 107-74-4(Hazardous Substances Data)

Usage

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.

Chemical Properties

Hydroxycitronellol has an odor reminiscent of rose and grape hyacinth.

Occurrence

Reported found in high bush blueberry, grapes, skim milk powder and white wine.

Preparation

By hydrogenation (under pressure in presence of Raney Ni) of 3,7-dimethyl-7-hydroxy-octan-1-al; also in good yields by catalytic hydrogenation (using Raney Ni) of 1,2-epoxy-3,7-dimethyl-octan-7-ol.

Aroma threshold values

Detection: 5 ppm

InChI:InChI=1/C10H22O2/c1-9(6-8-11)5-4-7-10(2,3)12/h9,11-12H,4-8H2,1-3H3/t9-/m1/s1

Upstream product

• 1564-98-3 6,7-epoxycitronellol 
• 1117-61-9 (3R)-citronellol 
• 7664-93-9 sulfuric acid 
• 7782-77-6 cis-nitrous acid 
• 106-21-8 tetrahydrogeraniol 
• 107-75-5 7-hydroxy-3,7-dimethyl-octanal 
• 106-22-9 Citronellol 
• 64-17-5 ethanol 
• 34212-48-1 (R)-7-hydroxy-3,7-dimethyl-octanal 
• 555-75-9 aluminum ethoxide 
• 2564-83-2 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical 

Downstream Products

• 107-75-5 7-hydroxy-3,7-dimethyl-octanal 
• 32779-58-1 2,6-dimethyl-hept-6-en-2-ol 

Relevant articles and documents

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Iron-catalyzed chemoselective hydride transfer reactions

A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.

Fe-Catalyzed Anaerobic Mukaiyama-Type Hydration of Alkenes using Nitroarenes

Hydration of alkenes using first row transition metals (Fe, Co, Mn) under oxygen atmosphere (Mukaiyama-type hydration) is highly practical for alkene functionalization in complex synthesis. Different hydration protocols have been developed, however, control of the stereoselectivity remains a challenge. Herein, highly diastereoselective Fe-catalyzed anaerobic Markovnikov-selective hydration of alkenes using nitroarenes as oxygenation reagents is reported. The nitro moiety is not well explored in radical chemistry and nitroarenes are known to suppress free radical processes. Our findings show the potential of cheap nitroarenes as oxygen donors in radical transformations. Secondary and tertiary alcohols were prepared with excellent Markovnikov-selectivity. The method features large functional group tolerance and is also applicable for late-stage chemical functionalization. The anaerobic protocol outperforms existing hydration methodology in terms of reaction efficiency and selectivity.

Hydroxyl citronellol and preparation method thereof (by machine translation)

The invention provides hydroxyl citronellol and a preparation method thereof. The method has the advantages of high yield and less three wastes, overcomes a plurality of problems in the prior art, and has a good industrial prospect. (by machine translation)