126-91-0

Basic information

• Product Name: (-)-LINALOOL
• Synonyms: (R)-(-)-3,7-DIMETHYL-1,6-OCTADIEN-3-OL;(R)-3,7-dimethyl-1,6;(R)-3,7-dimethyl-octa-1,6-dien-3-ol;L-LINALOOL 80+% NATURAL;coriandrol;coriaudrol;3,7-DIMETHYL-1,6-OCTADIENE-3-OL;Agarol
• CAS NO: 126-91-0
• Molecular Formula: C₁₀H₁₈O
• Molecular Weight: 154.25
• EINECS: 204-811-2
• Mol File: 126-91-0.mol

Chemical Properties

• Boiling Point: 198 °C(lit.)
• Flash Point: 174 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 0.87 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.17 mm Hg ( 25 °C)
• Refractive Index: n20/D 1.462(lit.)
• PKA: 14.51±0.29(Predicted)
• BRN: 1721487
• CAS DataBase Reference: (-)-LINALOOL(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-LINALOOL(126-91-0)
• EPA Substance Registry System: (-)-LINALOOL(126-91-0)

Safety Data

• Hazard Codes: C,Xi
• Statements: 36/37/38-34
• Safety Statements: 26-36/37/39-45-36-36/37
• RIDADR: UN 1760 8/PG 2
• WGK Germany: 3
• RTECS: RG5800000
• Hazardous Substances Data: 126-91-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
(-)-Linalool is used as a reactant in the enantioselective preparation of ophiobolin sesterterpene via diastereoselective reductive radical cascade cyclization. It also plays a crucial role in the total synthesis of (-)-5,6-dihydrocineromycin B via (-)-linalool O-triethylsilyl ether and the total synthesis of pladienolide B analog.
Used in Analytical Chemistry:
(-)-Linalool has been utilized as a reference standard in the quantitative determination of lavender oil in lavaflam tablets using the gas chromatography method of analysis (GC). This application highlights its importance in ensuring accurate and reliable results in analytical chemistry.

InChI:InChI=1/C10H18O/c1-5-10(4,11)8-6-7-9(2)3/h5,7,11H,1,6,8H2,2-4H3/t10-/m0/s1

Upstream product

• 216861-19-7 linaloxymethyl butanoate 
• 71-36-3 butan-1-ol 
• 115-95-7 linalool acetate 
• 121468-44-8 Toluene-4-sulfonic acid (2R,3R)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranylmethyl ester 
• 471-10-3 linalyl chloride 
• 68224-83-9 (R)-3,7-dimethyloct-6-en-1-yn-3-ol 
• 78-70-6 3,7-dimethylocta-1,6-dien-3-ol 
• 61573-90-8 ((2S,3S)-3-methyl-3-(4-methylpent-3-en-1-yl)oxiran-2-yl)methyl methanesulfonate 
• 137958-52-2 (2S,3R)-3-Benzyloxy-1,2-diacetoxy-3,7-dimethyl-6-octene 
• 137958-51-1 (2S,3R)-3-Benzyloxy-3,7-dimethyl-oct-6-ene-1,2-diol 
• 50727-94-1 (2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol 
• 106-25-2 Nerol 
• 86777-86-8 (S)-2,2,4-trimethyl-4-vinyl-1,3-dioxolane 
• 86832-97-5 (S)-1,2-Epoxy-2-methyl-3-buten 

Downstream Products

• 60047-17-8 2-methyl-5-(2'-propyl-2'-hydroxy)-2-vinyltetrahydrofuran 
• 6876-07-9 2,6-dimethyl-1,3,7-octatriene 
• 33303-08-1 2,7-Dimethyl-1,4,6-octatrien 
• 6138-90-5 geranyl bromide 
• 78-69-3 tetrahydrolinalool 
• 123-35-3 7-methyl-3-methene-1,6-octadiene 
• 106-24-1 Geraniol 
• 3016-19-1 alloocimene 
• 99-86-5 1-methyl-4-isopropyl-1,3-cyclohexadiene 
• 98-55-5 terpineol 
• 7785-53-7 4R-α-terpineol 
• 532-87-6 p-camphorene 
• 138-86-3 limonene. 
• 123-76-2 levulinic acid 

Relevant articles and documents

Tuning the catalytic performance for the semi-hydrogenation of alkynols by selectively poisoning the active sites of Pd catalysts

Semi-hydrogenation of alkynols to alkenols with Pd-based catalysts is of great significance in fine chemical industries. Industrial Lindlar catalysts, employing Pb to modify the Pd nanoparticles for higher selectivity toward alkenols, however, generally suffer from both a severe activity decrease and environment pollution caused by using heavy metal Pb and additives. Therefore, how to overcome the selectivity-activity paradox remains a great challenge in industry. Here, we report a controllable strategy for the synthesis of semi-hydrogenation catalysts, which successfully improves the catalytic performance through selectively poisoning the edge and corner sites of Pd nanoparticles. When the integrity of the crystal face is reserved, both higher activity (～1340 h-1) and selectivity (～95% at 99% conversion) are achieved in the semi-hydrogenation of 2-methyl-3-butyn-2-ol (MBY) in ethanol, an industrially important intermediate product for the synthesis of vitamin E, without adding any toxic additives. What's more, the yield could exceed 98% at 99% conversion under no solvent and organic adsorbate conditions, which had never been achieved before. This work provides a different perspective to design and develop high performance catalysts for semi-hydrogenation of alkenols or even substituted alkynes.

Structurally diverse glycoconjugated volatile compounds from Oxytropis falcata Bunge

A phytochemical investigation on the whole plant of Oxytropis falcata Bunge yielded 16 glycoconjugated compounds with structurally diverse volatile aglycones but similar sugars. Of these, five were previously undescribed compounds with different volatile aglycones but same glucuronic acid (1 → 2) glucosyl moiety, including three octanol glucuronic acid (1 → 2) glucosides (1–3), one acyclic monoterpenoid glucuronic acid (1 → 2) glucoside (4), and one 4-phenyl-butan-2-ol glucuronic acid (1 → 2) glucoside (5), and 11 were biological related known glucoconjugated volatile compounds (6–16) isolated from genus Oxytropis for the first time. The structures of these compounds were determined by extensive spectroscopic analysis of MS, 1D and 2D NMR data. The absolute configurations of aglycones and sugar residues were assigned via enzymatic hydrolysis and subsequently comparison of the specific rotations. This is the first report of such structurally diverse glycoconjugated volatile compounds from O. falcata, which might be regarded as the precursor of free volatile compounds, and presents scientific evidences for better clarifying the volatile compositions of this medicinal plant and genus Oxytropis.

Metal-organic framework Co(D-cam)1/2(bdc)1/2(tmdpy) for improved enantioseparations on a chiral cyclodextrin stationary phase in gas chromatography

Initial efforts to combine a chiral metal-organic framework (MOF), Co(D-Cam)1/2(bdc)1/2(tmdpy) (D-Cam=D-camphoric acid, bdc=1,4-benzenedicarboxylic acid, tmdpy=4,4′-trimethylenedipyridine), with peramylated β-cyclodextrins to investigate whether the use of a MOF can enhance enantioseparations on a cyclodextrin stationary phase are reported. Compared with columns of peramylated β-cyclodextrin incorporated in a MOF containing sodium chloride, the column of peramylated β-cyclodextrin+MOF shows excellent selectivity for the recognition of racemates, and higher resolutions are achieved on the peramylated β-cyclodextrin+MOF stationary phase. Experimental results indicate that the use of Co(D-Cam) 1/2(bdc)1/2(tmdpy) can improve enantioseparations on peramylated β-cyclodextrins. This is the first report that chiral MOFs can improve enantioseparations on a chiral stationary phase for chromatography. Copyright

Synthesis and reactions of the optically active selenols derived from monoterpenes Dedicated to Professor Jacek Gawronski on the occasion of his 70th birthday

A convenient methodology for the synthesis of optically active selenols, derived from p-menthane, carane, and pinane, is described. The selenols were oxidized with air to give the optically active diselenides, and were also converted into the corresponding allylic selenides via reaction with Z- and E-cinnamyl, geranyl, and neryl chlorides. Oxidation of the allylic selenides with mCPBA gave the optically active alcohols via [2,3]-sigmatropic rearrangement of the in situ generated allylic selenoxides.

Characterization of a novel esterase isolated from intertidal flat metagenome and its tertiary alcohols synthesis

A gene coding for an esterase (EstEH112) was isolated from metagenome originated from Korean intertidal flat sediment. The putative esterase gene encoded a 340 amino acids protein with characteristic residues of lipolytic enzymes such as a conserved pentapeptide (GXSXG), the typical catalytic S-D-H triad, and a GGG(A)X-motif in the oxyanion hole near the active site similar to the hormone sensitive lipase (HSL) family. p-Nitrophenyl butyrate was the best substrate for the enzyme among the other p-nitrophenyl esters investigated. The apparent optimal temperature and pH for EstEH112 was 35°C and at pH 8.0, respectively. EstEH112 efficiently catalyzed the hydrolysis of various large tertiary alcohol esters. These characteristics of EstEH112 make it a potential candidate for application in biocatalysis.

Enantioselective synthesis of allylboronates bearing a tertiary or quaternary B-substituted stereogenic carbon by NHC-Cu-catalyzed substitution reactions

Allylic substitutions that afford α-substituted allylboronates bearing B-substituted tertiary or quaternary carbon stereogenic centers are presented. C-B bond-forming reactions, catalyzed by chiral bidentate Cu-NHC complexes, are performed in the presence of commercially available bis(pinacolato)diboron. Transformations proceed in high yield (up to >98%) and site selectivity (>98% SN2′), and in up to >99:1 enantiomer ratio. Trans- or cis-disubstituted alkenes can be used; alkyl- (linear as well as branched) and aryl-trisubstituted allylic carbonates serve as effective substrates. Allylboronates that bear a quaternary carbon center are air-stable and can be easily purified by silica gel chromatography; in contrast, secondary allylboronates cannot be purified in the same manner and are significantly less stable. Oxidation of the enantiomerically enriched products furnishes secondary or tertiary allylic alcohols, valuable small molecules that cannot be easily obtained in high enantiomeric purity by alternative synthesis or kinetic resolution approaches.

An efficient procedure for the 1,3-transposition of allylic alcohols based on lithium naphthalenide induced reductive elimination of epoxy mesylates

An efficient protocol for the 1,3-transposition of allylic alcohols has been developed. The method is based on the pretransformation of allylic alcohols into the corresponding epoxy mesylates, followed by the reductive elimination of the resulting epoxy mesylates by using lithium naphthalenide (LN) as a reducing agent. Georg Thieme Verlag Stuttgart.

Enzymatic alcoholysis of alkoxymethyl alkanoates: A possible approach for the kinetic resolution of tertiary alcohols

The pivaloyloxymethyl and butanoyloxymethyl derivatives of tert-butanol and linalool (1.4) are readily accepted by hydrolases. Linalool derivative 4b is alcoholysed stereoselectively by Candida rugosa lipase (E=9.7).

Asymmetric [2,3]sigmatropic rearrangement of optically active allylic selenides

Oxidation of an optically active allylic selenide derived from L-proline 1 with m-chloroperbenzoic acid afforded the corresponding chiral allylic alcohol 3 via asymmetric [2,3]sigmatropic rearrangement with fair enantioselectivity (up to 66% e.e.).

One-pot transformation of p-toluenesulfonates of 2,3-epoxy alcohols into allylic alcohols

A convenient and efficient method for the synthesis of synthetically useful non-racemic allylic alcohols from 4-methylbenzenesulfonates of non- racemic 2,3-epoxy alcohols is described. Satisfactory yields are obtained by treatment of 4-methylbenzenesulfonates of non-racemic 2,3-epoxy alcohols with potassium iodide followed by zinc powder and ammonium chloride in a one-pot manner. The method has been successfully applied to the synthesis of a key building block of C30-C37 botryococcenes.