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

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

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

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

Downstream Products

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

Relevant articles and documents

An Iminium Salt Organocatalyst for Selective Aliphatic C-H Hydroxylation

The first examples of catalysis of aliphatic C-H hydroxylation by an iminium salt are presented. The method allows the selective organocatalytic hydroxylation of unactivated 3° C-H bonds at room temperature using hydrogen peroxide as the terminal oxidant. Hydroxylation of an unactivated 2° C-H bond is also demonstrated. Furthermore, improved functional group compatibility over other catalytic methods is reported in the form of selectivity for aliphatic C-H hydroxylation over alcohol oxidation. On the basis of initial mechanistic studies, an oxaziridinium species is proposed as the active oxidant.

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.

Visible-Light-Driven Dehydrogenative Coupling of Primary Alcohols with Phenols Forming Aryl Carboxylates

A preparative method for obtaining aryl esters from aliphatic primary alcohols and phenols was developed. The reaction proceeds under the irradiation of visible light at ambient temperature, dispensing with any oxidant or hydrogen acceptor. Primary alcohols having a variety of functional groups are successfully esterified with phenols. The produced esters can be utilized as the precursor of various carbonyl compounds.

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.

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)

IMINIUM SALT ORGANOCATALYSTS, METHODS OF MAKING, AND METHODS OF USING

Aspects of the present disclosure include compositions comprising iminium catalyst, methods of making, methods of using, and the like.

Iron(III)/NaBH4-mediated additions to unactivated alkenes: Synthesis of novel 20′-vinblastine analogues

An Fe(III)/NaBH4-mediated reaction for the functionalization of unactivated alkenes is described defining the alkene substrate scope, establishing the exclusive Markovnikov addition, exploring a range of free radical traps, examining the Fe(III) salt and initiating hydride source, introducing H2O-cosolvent mixtures, and exploring catalytic variants. Its use led to the preparation of a novel, potent, and previously inaccessible C20′-vinblastine analogue.

Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues

Full details of the development of a direct coupling of catharanthine with vindoline to provide vinblastine are described along with key mechanistic and labeling studies. Following an Fe(lll)-promoted coupling reaction initiated by generation of a presumed catharanthine radical cation that undergoes a subsequent oxidative fragmentation and diastereoselectivecoupling with vindoline, addition of the resulting reaction mixture to an Fe(III)-NaBHVair solution leads to oxidation of the C15'-C20' double bond and reduction of the intermediate iminium ion directly providing vi nblastine (40-43percent) and leurosidine (20-23percent), its naturally occurring C20' alcohol isomer. The yield of coupled products, which exclusively possess the natural C16' stereochemistry, approaches or exceeds 80percent and the combined yield of the isomeric C20' alcohols is >60percent. Preliminary studies of Fe(III)-NaBHVair oxidation reaction illustrate a generalizable trisubstituted olefin scope, identify alternatives toO 2 trap at the oxidized carbon, provide a unique entry into C20' functionalized vinblastines, and afford initial insights into the observed C20' diastereoselectivity. The first disclosure of the use of e xo-catharanthine proceeding through ?19'20'-anhydrovinblastine in such coupling reactions is also detailed with identical stereochemical consequences. Incorporating either a catharanthine Λ/-methyl group or a vindoline Λ/-formyl group precludes Fe(lll)-promoted coupling, whereas the removal of the potentially key C16 methoxy group ofvindoline does not adversely impact the coupling efficiency. Extension of these studies provided a total synthesis of vincristine (2) via &Lamb da;/-desmethylvinblastine (36, also a natural product), 16-desmethoxyvinblastine (44) and 4-desacetoxy-16- desmethoxyvinblastine (47) both of which we can now suggest are likely natural products produced by C. roseus, desacetylvin-blastine (62) and 4-desacetoxyvinblastine (59), as well as a series of key analogues bearing systematic modifications in the vindoline subunit. Their biological evaluation provided additional insights into the key functionality within the vindoline subunit contributing to the activity and sets the foundation on which further, more deep-seated changes in the structures of 1 and 2 will be explored in future studies.

Coupling reaction of alkyl chlorides with silyl enolates catalyzed by indium trihalide

Indium(III) halide catalyzed not only the coupling of alkyl chlorides with silyl enolates derived from esters, ketones, and aldehydes to give a variety of α-alkylated carbonyl compounds but also one-pot, three-component reactions of aldehyde enolate, alkyl chloride, and allylsilane or alkynylsilane.