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

Hydroxycitronellol is a natural organic compound with a pleasant, floral odor reminiscent of rose and grape hyacinth. It can be synthesized through various methods, such as hydrogenation of specific precursors using Raney Ni as a catalyst.

Uses

Used in Fragrance Industry:
Hydroxycitronellol is used as a fragrance ingredient for its distinct rose and grape hyacinth scent. Its aroma threshold value of 5 ppm allows for effective use in creating various fragrances for perfumes, cosmetics, and other scented products.
Used in Flavor Industry:
Due to its natural, pleasant aroma, Hydroxycitronellol can also be used as a flavoring agent in the food and beverage industry, adding a unique and appealing taste to various products.
Used in Essential Oils:
Hydroxycitronellol can be found in essential oils derived from plants such as high bush blueberry, grapes, skim milk powder, and white wine. It contributes to the overall aroma and scent profile of these essential oils, making them suitable for use in aromatherapy and other applications.

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.

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

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

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.

Cyclopentadienone iron tricarbonyl complexes-catalyzed hydrogen transfer in water

The development of efficient and low-cost catalytic systems is important for the replacement of robust noble metal complexes. The synthesis and application of a stable, phosphine-free, water-soluble cyclopentadienone iron tricarbonyl complex in the reduction of polarized double bonds in pure water is reported. In the presence of cationic bifunctional iron complexes, a variety of alcohols and amines were prepared in good yields under mild reaction conditions.